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Kara Connolly
Was even bad in America.
Theo
You know, I'm not home a lot. You know, I can't keep a plant alive at the moment. But when I am home, my bedroom is. It's like my sanctuary. You know, it's. It's a sacred spot for sleep. Thankfully, I have a Helix sleep mattress. God, I like it. I mean, I get on that thing and Who? Baby girl, before I know it, it's morning, and I'm feeling good. In fact, I like mine so much, I got two of them. I put one of them in the guest room over there in case mom wants to come and just launch some of her dirty dreams into that thing. Because, honestly, sleep matters more to me than ever, especially when I'm on the go, if I'm home, you know it. Days are long when you shut it down. It's time to shut it down. Getting real sleep on my Helix sleep mattress makes all the difference. If your old mattress has you just launched in, locked in a trench over there, you need a ladder to get out that thing. It may be time for you to give Helix sleep a try. You can sleep great, too. Just go to helixsleep.comtheo to get 25% off site wide for our audience only. That's helixsleep.comt h e o Make sure you enter our show name after checkout so they know that we sent you if you're running a business. Before we begin, I'd like to say that some of the conversation from today is kind of graphic in nature. We're talking about police work and detective work, and some of it's intense. If. If those types of conversations are not for you, then please make that choice for yourself. Thank you. Today's guest is a retired Boston police officer and detective. She had over 20 years on the force before she joined the human trafficking unit and fought criminals in that world. We learned a lot about what it's really like out there, and I want to thank her for her service. Today's guest is Ms. Kara Connolly. Yeah, my hair. I've been losing some hair because of stress.
Kara Connolly
Yeah, it happens. Sucks. Just go in the sink and you got handfuls. Yeah.
Theo
You just wake up and it looks like you look back, you're like, oh, my pillow.
Kara Connolly
Yeah. Yeah, it's gross.
Theo
Your pillow's got sideburns on it or something. You know, your pillow's using a curling eye.
Kara Connolly
It's a mess. Yeah.
Theo
That's way too much. You've dealt with it.
Kara Connolly
Yeah. In the past. Yeah.
Theo
Yeah. And it was a stress from work.
Kara Connolly
Yeah. And other Things. But the, the minoxidil definitely helps because I was, I called my doctor and like, oh, she can't see you for nine months. And I was like, well, my hair's falling out. And they're like, well, you could see the nurse practitioner in two months. I was like, no. So I went to one of those online things and they sent me a minoxidil in like three months. I had little bald baby hairs sprouting out. It came back. So it does help.
Theo
Yeah, yeah, yeah. That's what I'm realizing. I just got to. Yeah. Just taking some time just to enjoy, do things. Just that I enjoy. That's what I'm, that's like my focus right now is just to do things that I enjoy because I'll, I'll let added stress stay on me as well, you know.
Kara Connolly
Yeah, of course that's what I'll do.
Theo
Yeah. And not realizing that everything's going to be okay, you know, that's my, my.
Kara Connolly
Boyfriend say, what does someone. I was nervous about today? And he's like, it's all gonna be okay.
Theo
Yeah, it really is. Yeah, everything's gonna be okay. Kara Connolly, thank you so much for joining us. You are a retired police officer and detective from Boston.
Kara Connolly
That's correct.
Theo
And you were on the forces for 30.
Kara Connolly
31 years.
Theo
31 years, yeah. And you started out in Dorchester, I think.
Kara Connolly
Yeah. When I graduated the police academy, they send you to a couple different places to tell you you're on probation or whatever. And I went to a part of the city called Dorchester.
Theo
Wait, probation? They send.
Kara Connolly
So when you, you join the police department, you go through the police academy.
Theo
Okay.
Kara Connolly
And then when you get out now they do it for a year, but when I did graduated, it was six months. And they have you, you basically it's probationary period to see if you're, you know, good enough, behave enough. I do the right thing for like six months. So they send you to a couple different places, like one busy district, one quiet district.
Theo
So they start you like a probationary period somewhere.
Kara Connolly
Yes. And you might stay there, they might move you, but that's how you're on probation for six months and then you're, you know, a full time police officer after that.
Theo
Okay. And what were those first years on the force like? Like in South Boston, was it?
Kara Connolly
Yeah. So I was actually born South Boston, so I was in Dorchester and I was in South Boston. So Boston at the time was a quieter district. Dorchester was very, very busy. In the 90s was like in Boston was a ton of shootings and gang stuff. So comparatively speaking, South Boston was a quieter place to end up for several years.
Theo
And what were the demographics of that area? Like where you were servicing kind of everywhere?
Kara Connolly
Dorchester's a different demographic than South Boston, population wise. Now South Boston's very hip and it's all young kids, but at the time I would say it was all just kind of families. Pretty quiet place at the time compared to other districts where a shooting every couple of days.
Theo
And is it mostly white, black, Latino, Asian?
Kara Connolly
Dorchester at the time when I was first, there was a lot of black, some white, some Asian. And South Boston at the time was mostly white, but some black and Latinos got it.
Theo
And who are the people they call Southies? Because you hear that a lot.
Kara Connolly
Southies is not a thing. You could say you're from Southie, but it's not pluralized. There's no s on the end of it. So I'm from Southie, but I never said that growing up. We always said South Boston, but most people said I'm from Southie.
Theo
Okay.
Kara Connolly
It's just a nickname for the part of town.
Theo
Right. So you're not like. But do other people call you Southies or the Southies?
Kara Connolly
No, people from like out of the city who hear about it became popular because it was in Goodwill. Hunting was up Austin. So that's kind of what put it on the map. So when people started moving there and didn't know any better, that's how they would say it. But people who grew up there back in 70s, 80s or whatever didn't say it like that. That pub that they, you know, they filmed in became like a big thing. El Street Tavern. And that was like around the corner from where I grew up.
Theo
And. And were the people there distrustful of police at the time? What was the relationship like between no.
Kara Connolly
People in Southie, like, like the cops compared to other parts of the city? I think in my experience, I mean, it was a quiet place when I worked there. Most of the stuff that kind of good stuff that happened or whatever crazier calls I've been on happened when I was a detective. Patrolman was pretty quiet.
Theo
Do you remember one of your first, like big like calls as a patrolman that was like, oh, this is real. Like, do you remember that? Like a first moment where you're like, this is pretty real?
Kara Connolly
Well, a lot of the calls, it's funny, a lot of the calls when it comes in, like person with the gun call. Like, I still remember my first person with the gun call. I was shit in my pants. Cause I was like, oh, my God, you know? And it turned out to be bullshit. It wasn't even real. So a lot of the calls are like that. You don't know they're fake until you get there. So you're like your adrenaline dump in the car and you're like, oh, my God, this is real. And I remember being like, what am I gonna do? Nothing. It was a big nothing burger.
Theo
Were you putting lipstick on or what? I mean, what do you even do?
Kara Connolly
No, there was no lipstick when I was a patrolman. No. Yeah.
Theo
Like, would you, like, powder up your face a little bit or something?
Kara Connolly
Just like, oh, no one powdered their face on the way to a call, huh?
Theo
That wasn't it?
Kara Connolly
No, that wasn't a thing.
Theo
Yeah, that's just in Charlie's Angels, huh?
Kara Connolly
Yeah.
Theo
What was it like being an officer in the 90s in that time period? Like, was that way different than you think it is now?
Kara Connolly
Yes, I think so. I mean, obviously the. The gang, the. The rate of shootings in Boston was much higher than. I forget what the highest homicide rate was in the early 90s. It might have been like 150, 160 people. Now Boston has like 35 a year. So it was a big difference. It's become much safer. Whether everyone's a gang's kind of aged out and they all went to jail or, you know, got shot or moved on in life. Whatever happened, it became much safer.
Theo
I'd say there's no money in being in a gang either. I think a lot of people are like, oh, this is a shitty business, you know, this says 1990, the homicide peak. Boston's homicide count hit an all time high of 152 cases, with much of the violence concentrated among youth and involving firearms. The spike was driven by gang violence, crack cocaine epidemic, and easy access to handguns.
Kara Connolly
Yeah, so 90s are a little different than now for sure.
Theo
Compared to then. How do you feel like police work is different between now and then? Do you have any thoughts on that?
Kara Connolly
I don't know. I mean, the whole, like, community policing aspect started when I was new, so that. That's kind of still progressed along, I think.
Theo
What does that mean, community policing?
Kara Connolly
Well, that's what they call it at the time. They had walking beats. So when I got on, you wouldn't be in a cruiser. Like, you'd walk the neighborhood kind of like they do in New York City. They have people walking around. There's not a lot of cruisers. And so they would put people in certain Parts of the city, like when I got on, for example, and I worked in Dorchester, I think there were like, seven or eight walking beats up and down, like, kind of the main street in the town. And now, excuse me, there's only a couple, and they just put those on again. So they're kind of trying to get back to that. So that was very different. Like, people who did the walking bits full time, like, knew everyone in the neighborhood. That was. The whole purpose is to get people into the neighborhood so people feel comfortable speaking to the police. Except the neighborhoods where they put the walking beats were usually the worst neighborhoods, and people didn't give a shit. They didn't want to talk to us, so.
Theo
Oh, it didn't matter anyway.
Kara Connolly
No, not the parts of the city where they had them. Now it's different. They don't have as many walking beats at all. They push a lot of the social media stuff. Like, the dancing cops is the fucking worst. It's so cringy.
Theo
And.
Kara Connolly
And the department. All the police departments do that. They put it out to try to be like, look, we're excessive. Oh, see, it's so, so embarrassing.
Theo
I haven't even seen this.
Kara Connolly
It's just. It's so goddamn cringy.
Theo
Are these real cops?
Kara Connolly
That's usually the. I don't know about them. Yeah, it says they are.
Theo
Oh, my.
Kara Connolly
Well, at least. At least they can dance. Like, when. When our department puts it out, it's like, she's like, red cops. Like, look, we're playing basketball with the kids, and you know what let's all do? Especially during COVID It's just. It's so cringy. They just point out the other day for female woman law enforcement day, and they had, like, women dancing. Some of my girlfriends and I sent it back and forth like, this is.
Theo
So who wants to see? Dude, the last thing I want is my cop dancing over there.
Kara Connolly
Is that what you're looking for when you call for help? Someone to show up and start dancing like you want someone who's gonna give you a hand? Yeah, it's just. I know they're trying to soften their image. They don't want to look, like paramilitary anymore. They want to look friendly and not scary and whatever. Whether it works or not, long term, I don't know.
Theo
Yeah. You get promoted to detective in 2005?
Kara Connolly
Seven.
Theo
2007.
Kara Connolly
Yeah.
Theo
Okay. And what is. What. What does it mean to. To become a detective? What does that mean exactly?
Kara Connolly
So to become a detective, back then, you had to take an exam, so it's like a six month, two year long process. You have to study for several months and there's like six or seven textbooks you have to read. So you take the exam and then they do kind of like an oral interview, depending on how you score on the test. And then they kind of combine your years of training and experience, your test score and your interview to say, okay, these people have a high enough score to get made detect. And then you do like a month's worth of training back at the police academy to. Because being a detective versus a patrolman, it's very, very different. First of all, you don't wear a uniform, which is my favorite part, but it's just completely different job. Like you're now responsible cop gets a call, they go to the call, they write a report and that's the end of it until they have to go to court. If the report that the cop writes about it gets assigned to a detective and now you own that. So you have to follow through. You have to follow up and go to court or take out criminal charges or whatever. So it's a very different job.
Theo
Is there a lot of lobbying to become a detective like whenever you're like on the force or people like I want to be detective and, and then do people. Is there any way to manipulate things so it betters your chances of becoming a detective? Or is it not like that?
Kara Connolly
Not like that. So everyone, if anyone's a patrolman, doesn't want to be a patrolman for long. I was a patrolman for 13 years, which was a long time. We had usually they do the detectives exam every two or three years and for some reason we had a seven year break because I didn't take it. I just had a child and I was like, I'll take the next one a couple years. And it was seven years. So I was a patrolman for a long time. So people wanted.
Theo
It was seven years to the next promotion.
Kara Connolly
Yeah, till the next exam. So it was a long wait. But people want it just because it's better than being a patrolman. Some people love being a patrolman and will do that their entire life. But most people either want to take an exam and become a supervisor, like a sergeant, a lieutenant, and keep kind of going up the chain, or people are interested in being a detective, so it's definitely desirable, you know.
Theo
Do you remember an early case as a detective that really kind of stood out to you?
Kara Connolly
Yeah, I had a good armed robbery once, you know, that sounds like an October on a good armed robbery.
Theo
Great. I Love a good armed robbery.
Kara Connolly
It was on Halloween, which is always one of the worst days of the year to work. Fourth of July, Halloween sucks. They're always crazy. But we had an armed robbery. It was a cell phone store. In the morning. It was in the morning. It was like 9:30 in the morning. The store just opened up and these two dudes went in and there was some girl, young girl, early 20s, working there by herself. It was in a shitty part of town. And they literally tied her up with like telephone cord around her wrists and her ankles and they stole. It was like 800 bucks or $785, whatever it was. But the feds ended up taking it because it was T mobile. And they can kind of loop in the commerce act, like by saying because commerce was halted with other states, it becomes like a federal case. But the guys ran and the girl. It was like something out of a movie. It was all on video. She literally hopped over to the phone all tied up with her ankles. And they put a gun to her head and everything. It was two got firearms. And she was terrified. And they. She hopped over to the phone and like, knocked it off with her head and was like calling for help.
Theo
At least she's in a phone store though. Like, at least, like.
Kara Connolly
But she was able to do that. And then it came in quick. So a couple of the guys from work, everyone I worked with, the best people on earth in Dorchester. They really were great, great cops. And they just kind of flood the area right away. And their descriptions going out. And one of the officers is actually one of my police academy classmates, ends up seeing these two guys walking down the street and a description of giving out clothing. They left like a trail of clothing down the street. They tried to drop everything and change their appearance.
Theo
It's hard to run and change at the same time.
Kara Connolly
Yeah. So they were just kind of. Yeah. Walking down the street and. Really nice. It's actually a little teeny. Is a nice neighborhood in this bad section of town. So they kind of stuck out and. But then he sees the trail of clothing, jackets and hats and shit left behind. So he called it in. These guys, one of them had on gloves, but the other one had band aids and tape around his fingers so he wouldn't leave any fingerprints. And as the guys, everyone went up there, the patrolmen were talking to him. He notices them gone. Like they're picking away to try to get the. The band aids and tape off their hands. And then another officer in the area was searching. She's looking in trash cans and she found the guns and then someone found the box, the money box. So that was a pretty good one.
Theo
It was an exciting one.
Kara Connolly
Yeah, it was just, it came together nicely. Everyone worked like, did so well together. Everyone was there at the right time to do the right thing. And then the feds took it. And they had serious criminal records. Both of them, one of them been doing armed robberies all over the city. It was like the same guy hit like five or six places. So we were glad to get him. They got. Because it was federal, they got like 20 something years. Each one of their brothers was a truck driver and he, that's how they got the guns. He was a cross country truck driver and he would, he bought guns in Arizona and then brought them back here.
Theo
So that's what made it federal, is that they were transporting guns across state lines.
Kara Connolly
I think they didn't end up prosecuting him because he basically testified against his brother.
Theo
But what made it such a big, what made the sentencing so severe because they were.
Kara Connolly
The way the feds do it in federal court is they basically add up. It's a point system and depending how many charges or cases, how many times you've been found guilty, then you were considered an armed career criminal and you get extra time added on.
Theo
Ah, got it.
Kara Connolly
But yeah, for 785 bucks they went to jail for like 20 something years each. It was crazy.
Theo
It's idiots.
Kara Connolly
Yeah, pretty much. That poor girl was terrified. I always felt bad for her.
Theo
Yeah. Oh, that would be so scary, dude. I don't know what I would do if someone did something like that. Like pull like, you know, she didn't.
Kara Connolly
Even want to identify them. We were trying to do like a, we do a bring back or show up, you bring. Because we brought them to say have her identify them and she was like hiding behind the blinds in the store. We usually have them like go out in the sidewalk and the person will like look through a car window. But she was literally hiding. She was absolutely terrified. She's crying and everything.
Theo
How important are fingerprints? Is that a real thing? How important is that when you were detective?
Kara Connolly
Well, that's a real thing because everyone's are different.
Theo
Yeah.
Kara Connolly
So if you get found at a scene, whether it's a break in or a robbery or something like that and they find your fingerprints. Well, what other excuse do you have for being there? So it's a pretty good. Especially now people like in court, when cases go to court, they don't want witness identification. They want. Because all the CSI shows they think we all have this bags of evidence to show when it comes to court. So juries want to see forensics. They want fingerprints. They want, like, cell phone records. They want DNA left behind because of the TV shows. Makes it look like that's left at every scene. But these guys covered their fingerprints. They had masks on. Like they put, you know, bandanas around their face. But the girl identified them from the clothes. One of them didn't have a mask on, but. So fingerprints are definitely very important.
Theo
And what's the process of actually lifting fingerprints? What is that? And you hear the term lifting fingerprints.
Kara Connolly
Different surfaces use different tools. Like this surface. The grain of the wood would be no good. You need like a smooth surface. Like, they train us on like granite, like countertops.
Theo
Oh, yeah, granite's nice.
Kara Connolly
Yeah, it's very smooth. It's shiny. So if someone leaves a fingerprint, you have, whether you have dry or oily hands, you're leaving oil behind. And you could take your powder and you spin the little powder on like a smooth surface, and literally the fingerprint pops. And then you just take this kind of clear square of like sticky tape and then like press it down and then lift it up so it transfers onto the outline. Transfers onto. There you go.
Theo
Can there be fingerprints in a place? Like, could you look at a counter or something and see nothing and there could actually be fingerprints there?
Kara Connolly
Yeah, you can kind of. If you use a flashlight, sometimes you can see it if it's a clean surface, if it's like a shithole house or filled. Like bank robberies, we don't do fingerprints because so many people go up to every teller. Like, even if a bank robber comes in and puts his hands down, there's 10,000 other fingerprints there from the people that came before you.
Theo
Right.
Kara Connolly
So they don't. We don't bother with something like that because you have to be able to show it's a suspect. So they won't like, put it into the system to see who it even belongs to.
Theo
Could a surface be so dirty that then the print itself actually makes it clean and that. You know what I'm saying?
Kara Connolly
Yes. On dirty windows, we get those on a break in when they push up. Push up a window and leave them behind. And you can literally see them because you can see sometimes they'll smear the dirt. Sometimes it's so dirty, though, the dust won't. The dust won't adhere to it.
Theo
Got it. What. What's a person who picks up the fingerprints? What do they call that person?
Kara Connolly
Well, we do it. Detectives.
Theo
Detectives do it.
Kara Connolly
Do it in Boston? Yeah, some in other places, like the crime scene tech will come out and other departments, but we do it ourselves. Unless it's like a major incident, like a homicide, then the homicide unit will call the forensic unit, like, and they'll. Those, those are civilians. They're not police officers, but they'll have, they have gone to school for that. So if it's like a major, you know, like I said, a homicide or something, they'll call in the crime scene text to do it. They don't want to mess with us.
Theo
And you ever have a day where it's just busy, you're like, oh, I got to get to my kid's birthday or whatever. I'm gonna just. We'll hope for the best on this when you take off.
Kara Connolly
Yeah, it sucks. Like, you could be. Your shift ends at 4:00'.
Theo
Clock.
Kara Connolly
If you work days and it, you know, 3, 45, someone, a person stabbed. All right, I won't be home till midnight, so.
Theo
Oh, you say oh, so you stay?
Kara Connolly
You stay.
Theo
Oh, yeah. I. I was saying, like, if you ever had a thing where it's like, I gotta get out of here, you know, I'm. Instead of doing the work, you know, instead of dusting for these fingerprints, I'm. Hit the road, you know, can't do that. You can'.
Kara Connolly
No, it's on you if it's your case, if you're on call. We call it catch day in Boston. But detectives, like, certain squads are in charge of all those calls that day. So five things could come in. We could get a shooting, a stabbing, an armed robbery, and a missing person. And they're all assigned to you. But it's not that busy. But it can be. You might have a day like, you don't even go pee. You don't even eat lunch. It's few and far between, but it definitely happens.
Theo
Wow, so you're just cruising like that?
Kara Connolly
Yeah.
Theo
How much. You mentioned television a little bit ago. How much is television and what people think and expect? How much has that affected, like, the prosecution of cases?
Kara Connolly
Ruined it. Absolutely destroyed it. Yeah. Everyone has such high expectations. If they watch, you know, CSI Miami or whatever the hell it is and see, they solve everything instantly. And they have cooperative witnesses or they have all these piles of evidence and like I said, people in. Because of that, people in regular juries and regular court cases expect. Oh, they literally come back with notes saying, why don't you have fingerprints? Why don't you have DNA? Like, why don't you have that? Well, not every Case has that, like I said, a bank. Robbie comes in, they don't touch the condom. We have no DNA. We have no fingerprints.
Theo
We have no semen either.
Kara Connolly
On eyewitness identification and videos now everywhere, video's huge. Video's a huge help. But it's definitely. The shows have been a detriment to prosecuting cases for sure.
Theo
So you think it's made that the shows have made it harder to prosecute cases?
Kara Connolly
Absolutely. Because people have higher expectations. The juries do.
Theo
The juries do. And they're like, oh, there's not enough here.
Kara Connolly
Yes. They'll be like, it's not. You don't have anything. Where's all. Where is everything? Like, well, we have a. You know, we've got the video and we've got this and that and like, no. So it's tricky. Yeah. It's not been our friend.
Theo
It's fascinating. It's. Yeah, it's fascinating because it kind of glorifies the sport of being detected, but at the same time ruined it. That's. A lot of things happen like that once things get glorified so much kind of, they get ruined sometimes. I think that's just almost a general rule of things. It feels like, except for God, probably. Everybody knows there are things they can do to reduce monthly costs and improve their finances. But who has time to go through all their expenses and decide what to trim? Rocket Money can relieve some of that stress and help you feel confident in the financial decisions you make. Rocket Money is a personal finance app that helps you find and cancel your unwanted subscriptions, monitors your spending, and helps lower your bills so you can grow your savings. Rocket Money's 5 million members have saved a total of 500 million in canceled subscriptions, with members saving up to $740 a year when they use all of the apps and premium features. Cancel your unwanted subscriptions and reach your financial goals faster with Rocket Money. Go to RocketMoney.com Theo today. That's RocketMoney.com T H E O RocketMoney.com Theo Bluechew, baby. You know it. Get on it. Bluechew. Bluechew is that upgrade button for your sex life. Chewable tablets that deliver stronger, harder, longer lasting erections without the hoops. No waiting rooms, no pharmacy lines, no people trying to tickle you while you're trying to. While you're trying to just manage your own life. Just a quick online visit. And once approved by a licensed medical provider, Bluechew sends the chews straight to your door. Guys, if you've been thinking about it. Now is the time to try BlueChew with your first month free. Yep, free great sex is just a few clicks away. Make life easier by getting harder and discover your options@bluechew.com and we've got a special deal for our listeners. Try your first month of BlueChew free. When you use promo code THEO, just pay five dollar shipping. That's promo code THEO. Visit BlueChew.com for more details and important safety information. And we thank BlueChew for sponsoring the podcast. You always, you always hear like the show's the first 48. Right. And my friend Chris D', Elia, he's a comedian, he's, he has this great joke. He's like the first 48. And I'm paraphrasing, he's like the first 48. It's like these detectives have 48 hours to solve the crime, but really they have as much time as they want.
Kara Connolly
Yeah, right. They do. We do. You know, sometimes you waiting on video, like it doesn't obviously if you don't have a suspect like right away, but if you work at it, sometimes the evidence is out there, you just have to find it. It might not slap you in the face at 10 minutes after the incident.
Theo
Right. But do you really only have 48 hours?
Kara Connolly
No, we have all the time you need. Except. Except it gets busy. And if I have three cases that day and if like I got to work on it and then two days from now I get another big one that like a shooting or stabbing or whatever, now your attention is split. So time is of the essence because something else is always going to happen. It's going to happen, something's coming. And whether you have a leisurely amount of time to work on the case, then you work it overtime, then you're working a double to try to stay and work on this case because another one could come in tomorrow. So it is this point to it. Like the 40 ads are important, but I think more so because something else is coming. So it's going to take the attention away. And then you can only be in so many places at once. You know what I mean? You can't, you can't.
Theo
Yeah, yeah, I never thought about that part of it. How do you prioritize what cases are most important?
Kara Connolly
I mean, obviously like if someone gets shot or stabbed, like that's a violent crime and you want that person who it's more defendant based, like at the kind of person that's going to do that. You want them off the streets. Right, right. And if you know, compared to, you know, identity fraud. Well, that's not an emergency. That. That can wait. You know what I mean? So those kind of like. Because we get a ton of fraud, that check fraud and all that shit, bank fraud. It's a nightmare because it's a lot of the times it's not even taking place. We have our victims in our city, but suspects are all over the country or all over the world.
Theo
Yeah.
Kara Connolly
So you can't prosecute them.
Theo
Yeah.
Kara Connolly
So it's. It's hard to chase down. So those are kind of. To the victim. It's not a lower priority. They're the one that had their money stolen or whatever. But it's not the same as being.
Theo
Shot or stabbed or having a criminal that's.
Kara Connolly
Yeah. Violent armed robbery or something.
Theo
You gotta find this guy now because obviously they're in heat for crime.
Kara Connolly
Yes, exactly.
Theo
Wow. So are there days when you kind of get to the end of your shift almost, and you look and you're like, oh, my God, there's still that one missing person I didn't reach out about. Or there's still this one thing.
Kara Connolly
There's always a pile, and now I.
Theo
Have to go do that.
Kara Connolly
Yeah. Oh, you very rarely get to go home at the end of your. Of your shift. You're always staying.
Theo
And how. What's it. What's that effect like on your home life? Like, were you able to have kind of a home life? Like, what was that like for you?
Kara Connolly
Yeah, I mean, it's. It makes it trickier for sure. You need help at home. It definitely makes it more difficult.
Theo
And were you able to have a family stuff? Do you have children?
Kara Connolly
Yeah. Nice.
Theo
Oh, your daughter's here.
Kara Connolly
My daughter's here.
Theo
Oh, nice. I forgot. Yeah, I didn't forget, but I think I just didn't know if she wanted to say it or not. Maybe too. So. Yeah. What was. So. Yeah. How do you. How do you manage that? Was that.
Kara Connolly
It's tricky. It was difficult. It was a lie. It was. It was hard. Yeah. Because you expected to come home. I get you to help them with some project or just got to make supper, and you have to call and be like, I'm not. I'm not gonna make it. Someone got stabbed or I gotta stay late. A lot of times, you know, you're gonna be like, okay. Those days, I know I can stay late because I have coverage with the kids or whatever. Yeah. But it's not easy.
Theo
But at least you had a good excuse.
Kara Connolly
Yeah. I mean, I wasn't out, you know, yeah, getting shit faced.
Theo
But yeah, I'm getting my nails done or I'm getting.
Kara Connolly
Yeah, I'm working.
Theo
Yeah. At least it wasn't like, yeah, I'm drinking or something or UCLUS is on third base. I can't, you know, I'm not going to be home on time.
Kara Connolly
Yeah, yeah.
Theo
Do you start to see where family life suffers? Do you see it like, you know, because that's also a common theme in a lot of like police serial programming and films and stuff where the detective is working late and then there's the family thing starts to suffer, you know.
Kara Connolly
I mean, I'm sure it did, but like I said, you kind of figure it out, you make it work. Yeah, you can. Like I was a detective in a busy part of the city. That's why I transferred to the human trafficking unit. Because that was like a Monday through Friday job, not a rotating schedule. Because I worked holidays. We worked every Christmas. You got a holiday off every six years. So. But you'd get all the holidays off that year. So that year you're getting, you know. Excuse me, you're getting Easter. Excuse me, please. Thanksgiving, Christmas, New Year's, you'll get all the biggies off, but then it's six more years until you get another one.
Theo
Wow.
Kara Connolly
So I went to human trafficking.
Theo
Drink some water real quick.
Kara Connolly
You're good. Horrific.
Theo
Sorry, miss. You are a detect. You are. I don't want to tell you what to do. Anything. Thank you for your service. That's what I'm saying. So it's six, so that. Wow. I just. That's wild.
Kara Connolly
Yeah.
Theo
So that time you get to spend with your family, it's really crucial.
Kara Connolly
Yeah. Especially holidays, you know, but if you're working different shifts, if you're working the midnight shift, you can kind of go home and sleep for a couple hours and then, you know, meet everybody at Thanksgiving. So that's how Boston worked. Obviously different cities do different things. We just had six squads rotating days off. But some units, like the human trafficking unit is Monday through Friday. So it's a little more normal if you have young kids or a family and you want being regular person, as I call it, and have Saturday and Sunday off like everybody else. Those units are better for something like that.
Theo
Got it. And I know you ended up in that unit. I want to talk to you about that in just a second. Take me through a couple more detective calls that were interesting to you or.
Kara Connolly
That really stood out, I'd say I always, my joke was always going to be that I was going to write a book. And the name of it was going to be Dick on the Sidewalk and Other Stories from the Street. The last few. The last few years I was a detective, I got like three of the craziest cases of my life. After third in year 31, we had some of the guy cut off his own dick and threw it on the sidewalk.
Theo
Oh, for what?
Kara Connolly
Because he was. He was crazy. He was mentally ill. But we don't know any of this. So the call came in in the morning. I was on the way in. It was early in the morning. It was cold out. I remember that.
Theo
Oh, yeah.
Kara Connolly
I have the radio on, and I hear the dispatcher call a car and then start to laugh. And then she says, disregard, we don't know what's happening. So I'm driving to the station, and then a call comes in again, sending a different car. Cause it was like the midnight shift ending, sending a different car. Hey, can you go to this location? Someone said there's some male And a piece of male anatomy on the sidewalk. And we were all laughing. We thought it was. We just thought it was a dildo. We thought it was a joke. That's why the dispatcher was laughing.
Theo
He just thought it was like a WNBA game or whatever.
Kara Connolly
Exactly. It wasn't green. Call comes in, like 10 minutes later. And my detective that I was working with at the time looked it up on the computer to see the text of the call. Like, what does this actually say? And then we saw that the caller was from a nearby health center. And it said there's, you know, it look, appears to be a penis on the ground. There's blood everywhere. We're like, oh, shit, that's not fake. So the patrolman.
Theo
Yeah, that's real.
Kara Connolly
The patrolmen go up there, and so that's our starting point. We don't know anything else. And literally, there it is. I wasn't there yet. The patrolman see it on the sidewalk, and there's a blood trail. So they start following the blood trail, and it went a long way, several hundred yards. And it gets worse and worse. So that's how it starts. So that's our starting point. And the patrolmen follow the blood trail. And then they're following it up the stairs of this three family house. It's like three apartments, one house. And the blood gets bigger and bigger. They knock on the door. This guy opens the door completely naked. A hole where his dick used to be. And he's just standing there, not talking. And they're like, hey, buddy, you okay? Like and he's just like. He doesn't speak. He just stares at them so that they're new. They were newer guys. I felt so bad for them. That's a tough call. They weren't brand new, obviously, but that's a lot for young guys to see, this, right?
Theo
Oh, yeah. Just see some cock down the street or whatever.
Kara Connolly
Why don't you come in and sit down? So they. And turns out it was like a group home for mentally ill people, but there was no staff members or anything there. So there's three people in the house. It is a bloodbath. There's blood everywhere in the bedroom, the floor, the sink was full of it. So they find that, and they get on the radio and they're like, get us an ambulance, whatever. Because we don't know how does someone. Alive, right? So he's alive. So I get called, and me and another detective, my boss, went down, and it's on the sidewalk, and they're taking photographs or whatever, and they call. Once the ambulance find out he's alive, they just assume somebody had bled out somewhere and was dead or someone did it to somebody else. He's like, no, I did it. Like, oh, shit. Okay.
Theo
So he's being honest.
Kara Connolly
Yeah, well, he's just completely and utterly mentally. At some other point, he'd, like, cut off his own nipples. He said to let the devil out. So the poor thing was very mentally ill. He was young, early 20s. So once the EMTs find out this person's alive, now they want to try to collect it to see if they can reattach it at the hospital. So we had done our photos. I actually have a video of this whole thing. I pulled video from the street nearby. Surveillance video. That's how I know kind of everything after the fact. They come down to reattach it. And we had just done the photos. I didn't look directly at it. We. I can do.
Theo
Oh, never stare into it.
Kara Connolly
You do like a. You do like, a weird blurring. It's almost like when someone blurs out somebody's face, and that's what your brain does. You're like, I don't want to see that.
Theo
I want to see all of it.
Kara Connolly
It was. It was big. It was nasty. So they try to come down to take it off the sidewalk. They goes to pick it up, and.
Theo
What are they using? A spatula or whatever?
Kara Connolly
No, I. He had gloves on. He's using his hand, and he had.
Theo
This weird, like, as a pervert.
Kara Connolly
Clear cylinder. He was an emt. He had this, like, Cylinder thing. He was gonna put it in like.
Theo
One of those bank. Remember at the bank you would put that check in the thing and send it back up.
Kara Connolly
Literally like that. So he, dude, he goes to pick it up and it's been so cold. He's tugging it and it was frozen to the sidewalk.
Theo
No way. Like that guy from Christmas story. Bring that up.
Kara Connolly
Like his tongue. That's what happened to the poor guys.
Theo
Bring that up real quick because people forget that that can happen. Oh, yeah. Oh, and let's get. Just. Just to give us a. A descriptive visual. What kind of wiener are we talking about? And if we're wieners. Oh, I don't know if it's still. What kind of. What kind of wiener side, like, because that's just a sod walk wiener. What kind of wiener are we talking about?
Kara Connolly
It's big.
Theo
It was.
Kara Connolly
It was big and it looked purple. Oh, it was. Yeah, it was. It was a black guy and it almost looked purple. But he went to tug it and because it froze, he gave it a second tug and then it like. He didn't let go of it. It like air and this thing came out. I don't know if it was urethra. I don't know what the it was. I compared later to like a balloon. Streamer came like flying out the end.
Theo
Oh, that's some party confetti, baby.
Kara Connolly
Turned and dry heaved into the street. I've never thrown up at the job. I've never done it. I dry heaved into the street. I was like, what the. And some young patrolman who was there, and this is all on video, he's in his uniform and he does this little kicky, uncomfortable dance because he's like, oh my God, that was horrific.
Theo
Oh, he couldn't handle it like that.
Kara Connolly
No, exactly. And then later I pulled the video from the street. We're like, how did this get there? How did this guy get back to the house? He had cut it off several hours before in the house, walked down the street and he's completely naked. Nobody called police. This is the best part. There's people going to work. It's like three or four in the morning. Busy, busy street. Driving down the street. He's completely naked. What? No one called 911. And he's walking down the street and I have a video of it. He leans it's. He cut it, but it wasn't off altogether.
Theo
Oh, so he leans down, bro, that's.
Kara Connolly
Whoa. Tugs. And then threw it on the sidewalk. No. Oh, so.
Theo
So he tell me that part Again, he what? So he.
Kara Connolly
So I'm watching this.
Theo
So he leans. Tell me that part again.
Kara Connolly
So I'm watching the video and try to find him, like, what time this happened. And you just see this form. It's dark, and he's completely naked walking down the street. And all of a sudden he leans over. I'm like, what's he doing? And he's in the direction. It's kind of from the side direction of his crotch. You see his heart move like a tug. And then he just. Through it. And I. I remember when I pulled the video, I didn't know this had happened. I watched it and I pushed my chair back from the desk and screamed. I was like, what the fuck? The worst part is he came. So if you could believe something's worse, he came back about a half an hour later. He walked like a mile. They said that's what saved him, why he didn't bleed to death. It was so cold, it coagulated the blood. So he didn't bleed to death. He came back, and he's walking down the street, and as he sees it, he walks over to it and gets down on all fours and leaned over and kissed it.
Theo
Nuh.
Kara Connolly
And then got up and walked away. I thought he was going to eat it like a dog bone. Honest to God. I was like, what is happening? What is happening? He bent down, gave it a smooch, and got up and walked home. Oh, God, it was crazy. Oh, my God, the poor bastard.
Theo
Oh, let me tell. Because I got to go through a couple beats of that story, and dear God, let me just say that out loud so God knows that we're just alarmed by this. First of all, the fact that he cut it and it was just hanging there.
Kara Connolly
He didn't do the job.
Theo
Just like a piece of Memphis mistletoe just hanging there. That's so wild.
Kara Connolly
Yeah, it was nuts.
Theo
Like mistletoe at a Diddy party or something. And then he hugged it off. I can't even imagine. Because you've read, like, a little hangnail when you pull it off.
Kara Connolly
Kills. And this is like. There's a lot of nerve endings.
Theo
Oh, that's the ultimate hangnail. Yeah, that's the most.
Kara Connolly
That should be the name of my chapter. Not Dig on the Sidewalk. The ultimate hang.
Theo
That's the most hangiest nail. Yeah, that there is. Ike, when you said that, it got so visceral. I think for me, and I'm sure.
Kara Connolly
For anybody listening, most men get the.
Theo
Same reaction, and then I wonder what flew out of it. Pull that up on Perplexity. Because I'm thinking that's just a little.
Kara Connolly
You know, what it looked like in the photo. And when I saw it come out, you know what like, sausage casing looks like before there's a sausage in it? It's almost like skinny, opaque, kind of almost. I don't know how else to describe it. It's. It's like kind of gray and translucent. It was like a little small than my pinky. And this thing just flew out. I just could. Not even.
Theo
I. Yeah, that's just a little wiener. Funfetti, homie. Let's look at. No, give me a gander at it, man. I'm trying to get. I'm trying to get a gander. Yeah, let's look at the. But let's look at the parts here because it's. It's. It's fascinating to know. What is that?
Kara Connolly
Yeah, I don't know what. I don't know what the. It was.
Theo
That's a vagina. Oh, no, that's a wiener. Sorry. There's some these days you can't tell. The other day my buddy showed me a picture of his naked wife. She has a wiener. And I was like, all right, well, that's a surprise.
Kara Connolly
Yeah, maybe it's a urethra. Yes. Because see, the urethral opening goes down to the end. That's what it was.
Theo
God boy.
Kara Connolly
Yeah, it was. It was dicey. That was a dice. And I remember when we got the call, and I remember standing over it thinking like, where did I go wrong in my fucking Life? That it's 7:45 in the morning and I'm looking at someone's dick on the goddamn sidewalk. You know, I was like, wait, what did I do? What did I do to deserve this?
Theo
It's a question as old as time.
Kara Connolly
You know, it really is. Poor bastard.
Theo
I think a lot of women have asked themselves things like that overall, you know, and in hindsight, what. How does that even follow up? Do you guys keep that in evidence?
Kara Connolly
No, they tried to reattach it at the hospital. So they rushed him to the hospital with it. And they did attach it, but it didn't take. It was like a month later. They had to like take it off.
Theo
Yeah, imagine that month. Oh, my God.
Kara Connolly
So it's funny, because of the group home, we were trying to find out what is this kid's story, what's his name? Because the other kid in the house was not with it at all. Couldn't even. He was just sitting there playing video games. Of course it's like a bloodbath. So we're like.
Theo
It's hard to get the kids off the games.
Kara Connolly
Right. So. But these guys, they're like 20. So I call the supervisor of the group home and I was trying to get some information. He's like, oh, him. We're trying to find him an in house an in a placement in a hospital or a psych ward because he's, you know, he's been exposing his penis in group classes or whatever in group meetings. And I said, well you're late. You're a little late. Because he cut it off and threw on the side with the guy's like what? Like you could tell he himself because that's his how someone's supposed to be supervising.
Theo
Yes. Obviously somebody's supposed to be there making sure at the very least someone's not lopping off their own wiener.
Kara Connolly
Yeah.
Theo
And I just can't. I can't even imagine the month wait to know if. If it's going to take or not.
Kara Connolly
You know, I don't think he cared. But still just as I think he was obviously crazy. I know that's not the technical.
Theo
But you don't think he cared why?
Kara Connolly
I mean, cut off to begin with. He said he was letting the devil out. Like he's just extremely mentally ill. And I don't think he even kind of.
Theo
I mean, I think there's a part of a lot of people that think the devil lives inside of their Genesee. For some people.
Kara Connolly
Yeah. And like I said, he cut his. He cut his nipples off. He like carved something in his forehead. Like this poor kid was. Was really messed up.
Theo
It's heartbreaking that people go through so much and I, I just. But I can't imagine that month where you're waiting to see. Right. Like they have the bandages. It's almost doing it.
Kara Connolly
Like how do you. Oh yeah, I can't sit there while. And saw it all. And he didn't like.
Theo
Did he use a saw now? Let's ask.
Kara Connolly
No, it's just a big long kitchen knife. But you know, it was dull as dishwater. It was in some shitty group home. It's not some nice Henckels knife. You know what I mean? I'm sure.
Theo
Well, it's not like hands, those scissors.
Kara Connolly
It was like some plastic handled shitty kitchen knife. It was like this long.
Theo
You got to see the knife.
Kara Connolly
Yeah. We were up in the apartment.
Theo
Was it a. Basically knife you get like if you made your kids dinner, you give them a knife or your husband.
Kara Connolly
No, not a steak Knife, like, a little bit longer. Like, it would come in your knife.
Theo
Block for, like, carbon serrated or whatever.
Kara Connolly
I don't remember that.
Theo
God.
Kara Connolly
I don't think it was serrated.
Theo
I hope it was otherwise serrated.
Kara Connolly
Might be more jagged, but I think.
Theo
You would get it done pretty quicker. I don't know if we can. I mean, the more we talk.
Kara Connolly
God only knows how long he was working at it, because the bed, the whole bedroom. So the kid I was working with, thank God. God, he had been in the crime scene unit, so he would go into scenes all the time. Like, he. We. He put on Tyvek suit to go in because there's so much blood. We go stepping through it.
Theo
Oh, the wiener holds a lot, baby. That's the Lord spigot.
Kara Connolly
The Lord lots that day.
Theo
God boy. Definitely God. And who was the other kid? Just some honky sitting there playing double dragon or something.
Kara Connolly
He's sitting there. It's like a grown man with his legs crossed like. Like, you know, so, you know, that's weird. The crisscross applesauce.
Theo
Yeah.
Kara Connolly
He's sitting there, like, trying to. We're talking like, hey, do you know what happened? He's just, like, trying to look past us, like, because we're in the way of his game.
Theo
Played a game.
Kara Connolly
All right, this guy. Ain't this.
Theo
What game was it? Do you remember?
Kara Connolly
No, I was concentrating on other.
Theo
Wow.
Kara Connolly
Yeah. He's literally just trying to look around us.
Theo
I bet it was one player. They didn't have a lot of two player games at that time. Wow. Oh, my God. But the worst. Imagine you just. You're. You're. You're waiting. You're. They wrap your wiener. They. They do the repackaging. And I bet at that point it's almost like the masked singer. You're just waiting. They take it off and you're seeing like, okay, is this. What do we have here?
Kara Connolly
You know? Yeah. What's the result?
Theo
Yeah, do we have a Shaquille o' Neal here? Do we have a Mugsy Bogues here? You know, I think you're just waiting.
Kara Connolly
To see what you're gonna end up with.
Theo
Oh, that must have been horrible. The big reveal, you know, and they're like, move that bus. And then the bus takes off and you're weak and you're. And your. Doesn't work. Dude, that's the freaking worst. God, I hate that.
Kara Connolly
That was.
Theo
I hate that. Oh, that's harrowing.
Kara Connolly
Yeah, that was one.
Theo
That's harrowing. And it's cold. Was it so Cold outside? Was it hard to stand outside? Was it that cold?
Kara Connolly
We weren't outside that long once we took the photos. And when the EMT came down and collected it, there wasn't else much to do at that scene. So then we went up to the house, and it wasn't cold in there. We were outside for maybe an hour, 45 minutes.
Theo
I don't even remember because it wasn't.
Kara Connolly
Like 20 below, right?
Theo
But it was chilly, right?
Kara Connolly
Yeah, it was cold.
Theo
But the. The part for me, I think that'd be the wildest is say you are. You know, you're so cold, you run out there, you're looking at the. And then it gets too cold. You gotta run back into your car.
Kara Connolly
No, there was no running back.
Theo
And together you're, like, texting, like, all right, let's meet. Meet out there again in 30 seconds. Like, you know what I'm saying? Like, you're having to battle the cold so much.
Kara Connolly
No, not at that case.
Theo
You're like, oh, yes. Yes. Yeah, it's a black. And you have to go sit back in your car. Like, that's the part that we get, you know, having to build up the. Just to stay warm out there. Oh, God, that's insane.
Kara Connolly
Yeah, it was crazy.
Theo
And it is. And that's the kind of. It's like, you know, you're sitting there and then you're watching your kiddo blow out some birthday candles or something.
Kara Connolly
You go from that to something else. That was a day. Yeah, we went out for drinks after work that day.
Theo
Oh, yeah.
Kara Connolly
We're going out tonight.
Theo
Yeah. Off of black and tan, huh? That's what I'm saying, dude. I love some Johnny Walker.
Kara Connolly
Yeah.
Theo
There was another story to pivot. I know that you had mentioned whenever our producer, Nick, had reached out to you, and thank you so much for coming.
Kara Connolly
Of course.
Theo
I want to say thank you so much. You look lovely today, too. It's a really great outfit. Who chose that? You did.
Kara Connolly
I did.
Theo
Yeah. You did a great job.
Kara Connolly
Thank you.
Theo
There was a story you talked about finding someone had left a child.
Kara Connolly
Someone put a baby in a trash can. And I preface this right away by saying the baby lived. The baby was fine.
Theo
Okay.
Kara Connolly
But that call came in for Patrolman. There was, like, a senior housing on our district, and there was a gentleman who lived there, an elderly man, and he had someone who used to come and clean his house for him, and he called 911 because he said someone just had a baby in his house and then left with it in a bag. And it was crying. So the patrolman goes to the call and he goes up and talks to him. The apartment is pristine. There's no sign of a baby being born. He said she was in the bathroom. He's like, it's no, nothing happened.
Theo
Nobody had a baby.
Kara Connolly
So he called the officer, called an ambulance for a psych eval, saying, is this guy, the old man, something's wrong or he maybe has dementia? I just wanted to check on and make sure he's okay. So as the ambulance is pulling up again, I have this on video. That's how I remember the sequence. The ambulance pulls up and pulls in. There was like a horseshoe driveway, and they pull in the driveway, and just as they're doing that, a girl is walking down the street, maybe 50, 60ft away, maybe a little more from the apartment. And it's a very busy street in Dorchester. It's Dorchester Ave. And she's walking on the street, and there's a wrought iron trash can in the street. And she walks by and she hears something. She thought it was like someone put puppies or something in the trash. She hears something crying. She sees the ambulance, goes running over and waves him down and says, I think there's a baby or something in the trash can.
Theo
Wow.
Kara Connolly
So the EMT comes walking down the street. You could tell, he thinks she's full of by the way he's walking. There's no urgency.
Theo
But everybody in this neighborhood's full of.
Kara Connolly
There's no urgency to his gate. He's just like, okay. Because they get. They inundated with calls. They are buried all day long. He's like, all right, we're here for this.
Theo
But he goes walking over. He goes in the typical haunted trash can in Dorchester's.
Kara Connolly
He goes in, and you can see his reaction. He picks it out, and then it's crazy activity. He puts it on the. You could see this was all in the video, but you can't see exactly. You could see insane movement. All of a sudden, he's on the air. And at the same time, the officer was up in the house, said, like, what's the ETA of my ambulance? He never showed up. And at the same time, the girl had called 911 and said, There's a baby crying in a trash can. So this, like, is all kind of happening at once. So then we all go flying up there when they're like, yeah, there's a baby. We don't have a mother. We don't know what's going on. The woman I spoke to, the gentleman in the house. He said it was his cleaning woman. He had a different name for her. That wasn't her real name. Cause we're trying to track her down. Like, is she bleeding out somewhere? Is she hurt? Does she need help? What is the story?
Theo
She just had a child, maybe.
Kara Connolly
So he said she was in the bathroom for a couple hours. He thought she had stomach problems. And then she asked him, do you have a pair of scissors? And then she asked him for a bag. And then. Because I interviewed him, me and my partner, and he walks. He said she walked out of the bathroom and she had like a big tote bag with her, like her purse. And the baby was in the bag. And he could hear crying. He's like, what's that? Is that a baby crying? She's like, oh, this is nothing.
Theo
Yeah. And then walked out or whatever. So that's crazy.
Kara Connolly
Then on the video, you can see her walking down the street. And there's people coming toward her. And there's a gentleman passing her just as she gets to the trash can. She waits for him. And as he goes past, she looks around, pulls it out and goes right. Right in the trash can. So turns out she had gone in there, had the baby. She was at her 30s, she wasn't a kid. And she wasn't. Not mentally ill. She just didn't plan on keeping the baby. She had the baby how alone? I do not know. And then cleaned the bathroom. That's why it was so pristine.
Theo
When people think of women, like, that's the power. I mean, women. It's just like how she did that.
Kara Connolly
I do not know. She sat in the tub and had a baby with no help.
Theo
Women are powerful, man. And then to clean up the bathroom.
Kara Connolly
Cleaned it up.
Theo
But she also is a cleaning lady. I could understand, you know, that's why.
Kara Connolly
It was so nice. Yeah. When the.
Theo
She, I guess, has to hide her. I guess so.
Kara Connolly
Yeah.
Theo
Is. Did you determine that she's mentally unwell? No, she was fine.
Kara Connolly
Didn't want the baby. But we don't know any of this at the time, so we. All we have is a phone number. She signed in on, like the log at the senior housing. And she put a phone number down. And one of the patrolmen working at the scene, they blocked off the street. There were like helicopters overhead. This was like news. It was on the news. And one of the officers who was blocking the street, the traffic, we all get the phone number. And he starts looking through reports because he's sitting there blocking the street. He starts looking through reports because we don't have the right name. That guy gave us the wrong name, like the wrong age. He said she's a girl. She was in a 30s. To him she was a girl. Because he's in his 80s.
Theo
He's a pervert too.
Kara Connolly
So I'm not judging him.
Theo
I don't know him.
Kara Connolly
He said she's a good looking girl. So maybe you're right. The office, the patrolman starts looking through reports and finds a phone number attached to a different name. So then we start looking for. And we find the driver's lights like this again. All took like over an hour because there's a lot going on and headquarters is calling and everybody's like, this is huge, you know, so what this kid finds the kid's real woman's real name and phone number and they start pinging the phone. So it turned out she, after she put the baby in the can, walked down the street and got on the trolley, took the tea back to like to Mattapan, the train station, and then got on a train or a bus and went to her house in Milton. So we knew what her address was. While she's in transit, we're following, they're following the ping and she's like moving through the city. And then my supervisor and a couple of detectives, at least one met her at the house with an ambulance. So like this lady, we don't know what's going on with her. So her at the house and said like, hey, you gotta go to the hospital, are you okay? Like what's going on? They went in the house, she like rented a small in law or something in the house. They said there were no baby items. It was full term baby, there was no crib, there was no diapers, there was nothing. So she did not plan on keeping this baby. She had no intentions of doing that. Obviously she didn't have a single thing in the house. But they took her to the hospital, she was fine. They kept her in the hospital for a few days. But I mean she literally tied the bag in a knot. Like she tried to kill the baby. And that girl who walking by saved it because it was cold that day. She saved that. She saved that baby.
Theo
That's unbelievable.
Kara Connolly
That might never have been found. Like the city comes and dumps those trash cans, that baby's gone.
Theo
The odds that the girl happened to be walking by and hear it.
Kara Connolly
Yeah.
Theo
And do they re partner that child and that mother?
Kara Connolly
Well, I think she tried to kill it. So I don't know. The homicide unit came and took the Case. Why? I don't know. Because, you know, the baby lived, but it's obviously a biggie, so they ended up taking it. It took four, like four years to go through court. It was during COVID I remember people wearing masks when it was on the news. But it took like four years to wind its way through court. No jail time. I'm like, that's attempted murder. She tried to kill that baby. There's nothing wrong with her. She wasn't a scared 16 year old. You know what I mean? She was just. Her defense attorney tried to say that it was cultural and I'm like, do people throw babies in trash cans in her culture? What the fuck?
Theo
Was it a black or Asian? Mexican?
Kara Connolly
She was. She was Haitian. She's from Haiti. Like that's not cultural. Oh, shit, there she is.
Theo
Mother allegedly abandoned newborn and trash bin. And Dorotheus is charged with attempted murder.
Kara Connolly
Yep, that's her.
Theo
She.
Kara Connolly
She didn't serve any time. No, she got probation. Yeah. None of. We weren't very happy with that.
Theo
Well, yeah, because you just like the psychology of that person that's out in the world. How could they value life?
Kara Connolly
Yeah. She doesn't. At least not that life.
Theo
Yeah. And how could you probably value one of the most precious lives unless maybe there was some extra. I wonder if there was an extreme circumstance of how she had that child.
Kara Connolly
But we weren't told. We were in communication with the da. Like they never told us. Other than it being cultural. We're like, what the fuck culture is that? That's not a culture anywhere.
Theo
Yeah, well, the media makes it likes to make it easy.
Kara Connolly
Yeah. But I think it took so long because court cases were just dragging on because, you know, nobody worked during COVID except us or whatever. I think it like everyone just gets tired of it and wants to go away. I don't know. Crazy.
Theo
Yeah, I mean. I mean, stuff like that's harrowing, you know, I don't know how you can. I don't think there's a way to shed that skin if you're a police officer or a detective. Even though it may seem superficial, like in some ways you just move on and finish your day. There's got to be a part of you inside of you that stores a lot of that. That uncomfort and like.
Kara Connolly
Sure.
Theo
I mean, illness. It's got to be you kind of.
Kara Connolly
I'd say you learn how to deal with it. I dealt with things better years on my job than I did when I was new. You know, stuff that used to upset me. You have to. It's your brain safety mechanism, too, so you don't lose your goddamn mind, you know? I mean, you learn how to. That's why cops laugh at murder scenes. Like, it's, it's, it's. It's tension release. We're not laughing at a murder scene. Like, people are trying to talk and say, okay, a lot of people, that's. Everything's normal here. You know what I mean?
Theo
Like, yeah, when Brad White was in.
Kara Connolly
He was in brains on the street. And you're like, so you know, what are you going to get for lunch later? Like, we have to do something to distract. Distract your brain and you get better at it.
Theo
Yeah, that's this. This officer that we had in who came in was talking about. He worked in Los Angeles, and he talked about this one story where he had. A mother had called. Her son was going to commit suicide. She was worried. And. And he gets there and the mother comes out to greet him, tell him what's going on. My son's inside. While they're outside talking, the son kind of steps into the doorway on a screen door kind of, and takes his own life with a shotgun.
Kara Connolly
Oh, shotgun's messy, man.
Theo
So then there's. Now he's standing out here with the mother. So he has to console the mother at the same time. And now go approach this situation.
Kara Connolly
Right. So you, you have to do many. Like, you're like, oh, I just saw someone blow their head off with the shotgun. And the mother's screaming and on the ground, I'm sure. But yet it's still like, not a crime scene.
Theo
But it's an active situation.
Kara Connolly
It's an active scene. You have to lock it down. And there's a lot. They're chaotic, you know, and if you're. Especially if you're alone, there's only one or two of you, and there's a lot going on. They're very chaotic.
Theo
Yeah. I can't even imagine how things go from seeming real and normal to absolutely surreal. Like in a moment, almost like you're in a movie or a video game. I remember he said he walked into the. He had to push the door wouldn't open all the way. Cause the body was like.
Kara Connolly
The body's too heavy. Yeah, you have to push him out of the way.
Theo
So he's pushing this, and then he steps inside. And part of the brain matter had hit the ceiling and it fell down the back of his shirt.
Kara Connolly
Oh, I think this is a Vegas guy. This is the Vegas sergeant. I think I saw that on your podcast.
Theo
Well, I think Brad, he may have done. He may have been in Vegas for a bit. He may have been in la, I believe. But, but he, but just.
Kara Connolly
It's gross. Like I've stepped in that. Like, like, how do you. Like you said, how do you really.
Theo
Oh no, it wasn't him. That was Chris Curtis.
Kara Connolly
Yeah.
Theo
This other guy was Brad White. But just fascinating, fascinating story. But just hear it like, I don't think nobody else goes to work and has this horror movie. That can happen once once in a while.
Kara Connolly
Please. CMT's fire. That's kind of it. Yeah.
Theo
Yeah.
Kara Connolly
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Kara Connolly
Yes.
Theo
Leadership. Yeah, they do. What's that whole relationship like? Like, break it down for me. What that's like?
Kara Connolly
Well, it's.
Theo
It.
Kara Connolly
You know, obviously things are very politically charged right now, more so than they've been in the past, I think, in my experience. So it depends on if your mayor is supportive or not. Historically. I mean, I had several mayors on in 31 years as a police officer, and some are more supportive than others. And some DAs get elected that are just like, oh, we're not gonna make. Vandalism's no longer a crime. Larceny is no longer a crime. Shoplifting's no longer a crime. Well, the people in the stores are still calling us when someone's stealing $10,000 worth of shit. But the DA is like, not prosecuting. So now that's why shit's locked up in all these doors. It's the DAs who are like, you know, whether it's the Soros DAs or whoever the fuck they are that got elected that are softer on crime or whatever. That's your job as a district attorney to prosecute crimes. And those are state laws on the books. So if those laws are still on the books, then why aren't you prosecuting it? So that's why shit is locked up in cvs, because people can indiscriminately steal all over the country. They ended up getting prosecuted. We had one guy, it was him and his brother doing it. They were like two man wrecking team. Every CVS and Walmart, Walgreens, we added up just like one kid in one month. It was like $30,000 worth of shit he stole. Now, how is Target or CVS recouping that? They're not. That's gone. But the DA doesn't care. So if you have a, like, right now, there's a good DA in Boston, I think, and he's doing more to make, you know, working with the officers as a team. Like, we're on the same team here. We're just trying to prosecute criminals and help victims. And if, you know, the DA is not supportive of that, like, what about all those victims whose Houses are getting broken into or their property's vandalized, and the DA is like, yeah, we're not going to prosecute that crime anymore. What about the people whose shit's getting stolen and ruined or whatever? Like, don't you care about them?
Theo
Right. And don't you care about how they feel then about their city and about their country? And. And then you guys are the ones that have to deal with it on the street level.
Kara Connolly
Oh, everyone hates us.
Theo
They take it out on you. But. But still, if someone hates the mayor, they take it out on the police. I'm saying it's like, yeah. And you guys kind of can't probably speak up on it sometimes because you're in a position where you're working under that regime. Yeah, yeah. I think about that about the border, too, sometimes with like, you know, people illegally coming across the border, and then people can have whatever thoughts they want about people coming over. Right. I think everybody needs to be legally documented. That's here. However they figure that out. But, you know, but the people that matter mo. That they're. Whose opinion matters most to me are the people who live. Right. What about the guy right there, the border town who's trying to put his kids to sleep at night and they want to be able to feel safe. That just. Just because they bought a house somewhere.
Kara Connolly
Yeah.
Theo
That there's not people running through their neighborhoods, whether those people have good intentions or bad, but just with the fear. The fear that. That it puts in their families.
Kara Connolly
You know, it's just all quality life stuff. It's all quality of life issues. And they don't seem to get that because it doesn't bother them if they're living in some, you know, multi million dollar house somewhere or a nicer part of the city or state. It's not happening around them. Like you said, the people in the border towns, they don't have a choice.
Theo
Yeah. It's. Especially if there's. And if you. If the. What about the. The. The guy who's worked at CVS for 20 years and he loves it. Right. And he loves seeing people come in and he loves. Like, that's something. He knows some of the older people, he's watched them get older and come in and get their medicine, and he's watched one of them lose their spouse over the years, and now they come in alone. But he's like a smile in their life once in a while when they come in. And now he has to be of deterrent to crime.
Kara Connolly
Like they come in with trash bags.
Theo
Yeah. Oh, it's unbelievable.
Kara Connolly
Literally, just clear the shelf. They go and still sell all their stolen shit at, like, the smaller bodegas and convenience stores. So they sell when they steal all the detergent and, you know, all that. They still. In baby formula that's been locked up for years. They go and sell it someplace else.
Theo
I mean, babies are still.
Kara Connolly
Bodegas is buying it off them. They know it's stolen shit, so they're a fault. Fault, too.
Theo
Yeah.
Kara Connolly
But like I said, the employee. What about him? Like, he doesn't want to do that when he goes to work.
Theo
No. And then he has.
Kara Connolly
Not a cop. He doesn't want to do that.
Theo
He's not a cop.
Kara Connolly
Yeah. He'll not chase people.
Theo
Yeah. That's the thing. They've made it so that almost every person has to feel like a cop. And then also that every per. That there's not a lot of support out there. Who. And. And that's a sick thing. And our government does that from the top down. And I believe that they. There is a reason they do that. They want to erode a sense of community and they want to erode a sense of normalcy. And they're doing it.
Kara Connolly
Yeah.
Theo
You know, who's the mayor that they have now over there that's been supportive. Do you feel like.
Kara Connolly
Kara, we haven't had a supportive mayor. That's the D A. Kevin Hayden. He's supportive, our mayor.
Theo
Hey.
Kara Connolly
Hey.
Theo
Boy out of Newton, huh? What's Newton like? Is it good over there?
Kara Connolly
Newton's very, very nice city. Outside, it's. It's a different city than Boston.
Theo
Down in Newton over there, I definitely.
Kara Connolly
Caught some Newton's high end.
Theo
Newton is. Yeah. Oh, yeah. Yeah. Newton.
Kara Connolly
Big money to live in Newton.
Theo
Big Newton, they call it.
Kara Connolly
It was big money to live there.
Theo
Oh, God, look at that. A bunch of people.
Kara Connolly
Probably he's from there. I think he lives in the city now. He's Suffolk County. He's not attached to the city. He's Suffolk County. But our prior. Prior DA was. It was atrocious.
Theo
I bet every kid over there has a signed Tom Brady football. That's that kind of.
Kara Connolly
Well, he lived in Chestnut Hill, which is part of Brookline, and Newton, it's like sandwiched right in that neighborhood there.
Theo
Yeah, I bet all those kids have that dude. Yeah. How was the D A support been over there? So this is a district attorney now?
Kara Connolly
Yeah, he's good.
Theo
It was. He was he during your term?
Kara Connolly
He was there when I retired. Yeah.
Theo
He was appointed by Charlie Baker, preceded by Rachel Rollins.
Kara Connolly
Yeah. Thumbs down on her.
Theo
Oh, she was another. Yeah. District attorney.
Kara Connolly
Yeah.
Theo
And now. So she.
Kara Connolly
She became a US Attorney under Biden, and then she was, I believe, fired from U.S. attorney with some ethics violation or some such.
Theo
Oh, Biden would hire anybody. He was asleep. You fucking dude. He was fucking. Yeah, he would hire Fred Flintstone to find out.
Kara Connolly
Someone sending him to bed at night. She was a good fit. Oh, I'm sorry. She resigned before she was. She was canned.
Theo
Rachel Rollins was not formally fired, but resigned from a position in May 2023, filing multiple ethics investigations. And. Yeah. And I don't know exactly what happened here, but what. What's it like from one DA to it? Like, how can it.
Kara Connolly
Well, she's the one that decided when we weren't going to prosecute Larceny's shoplifting, vandalism, the minor crimes. And she used to say, those aren't Right. Those aren't. I forget which. What verbiage was used. It was like, they're not, like, not victimless crime, but they're trying to say that. No, they're not. Even if it's CVS or Target, a big corporation, they're still losing millions of dollars. It was her.
Theo
She. She.
Kara Connolly
She was one of the ones that was not supportive.
Theo
And do you think it's a DA in that space? Do you think she's making her own choices? Or do you think that's coming down from a higher. Do you allegedly. Do you think it's coming. Because it just seems crazy to say we're not going to prosecute.
Kara Connolly
How do you do that?
Theo
It's.
Kara Connolly
It's a state law. How do you decide what you're.
Theo
During her campaign, Rollins pledged to decriminalize certain offenses, such as shoplifting, drug possession.
Kara Connolly
Yeah.
Theo
Wanton. Oh, wonton. Or malicious.
Kara Connolly
Wanton. Malicious. Yeah.
Theo
Or property. Drug possession. Tend to distribute. What?
Kara Connolly
Yeah, it's crazy. That's why Mass and Cast. You've heard of the part of Boston. I don't know if you heard the part of Boston called Mass and Cast. It is a disaster down there. There's drug addicts everywhere. They're all over the streets destroying property. There's needles all over the city in South End in that area. It's kind of. It was. It was focused there, and now they've tried to kind of break it up the last few years because it was insane. And now they've pushed it out. Yeah, there was 10 cities down there. Look at this shit. Yeah.
Theo
And look. And some people say this is just a bill.
Kara Connolly
They have safe shoot up zones there. They're letting them shoot up heroin to per se in safe places.
Theo
Oh yeah.
Kara Connolly
So now the needles are all over the south end and the poor people in the south end, they pay a lot of money to live there. These are beautiful brownstones. And now there's people shitting in their front yards, throwing needles everywhere, breaking. Say one guy was breaking into a house while people was under construction. The second floor. This was just a few weeks ago. And there's a guy's family there with his kids and they had like an old key or something and they were breaking in and going to like shit in the floor on the second floor that was under construction. He went up and there's like a pile of human shit in his house. He's like, what is going on? They put up cameras. The guy was going in and out every night to like sleep on the floor in this house under construction and then shit on the floor.
Theo
It's like the emoji or whatever.
Kara Connolly
Yeah. Like, what is wrong with you?
Theo
What?
Kara Connolly
So that part of the city, I feel bad for people who live down there. That's Atkinson Street.
Theo
Yeah. Where is it?
Kara Connolly
It's Atkinson Street. It's near the jail.
Theo
Yeah. Well. And look. And a lot of people say this is just a bill's tailgate or something over here. I'm not saying that. Some people say this is a pinto tailgate. I'm not saying that. What we're saying is that this is a lot of drug use that's happening over there in this town in Boston. But here's another thing though. They have this everywhere now.
Kara Connolly
Oh, it's everywhere.
Theo
Every city has this.
Kara Connolly
Every democratically run city. I think I could be wrong.
Theo
Well, we don't have one here. I know that. I hope not. Anyway. I don't know.
Kara Connolly
Austin got ruined. Austin was a blast. And I took my daughter there several years. I'd been there 10 years ago. And I was like, this is the coolest place. Reminds me of here a little bit. Like 6Ass 6th street where all the bars used to be. And then I went back a few years later because my daughter's way into music. I wanted to take her and she was afraid to get out of the car. There were homeless people sleeping in hammocks strung from street signs in the street. And it was just rampant before they. Like if you were homeless, you got arrested.
Theo
There was. Yeah.
Kara Connolly
Which isn't the best thing, but you got to do something. They're like throwing bricks through all the windows that have been there a Long time. Austin got ruined. Seattle's a hole. Portland. Yeah.
Theo
Portland is. I'll have to sneeze, but Portland is a. But also. It's awesome. I will say this.
Kara Connolly
Yeah. I was up there when I do landscape photography as a hobby, or it used to. And I tried. Went up to Oregon and in Washington, and I love. It's the coolest place. Like, it's such a cool vibe.
Theo
That element that's out there. It's like, why are we.
Kara Connolly
It's like, I don't know, their end game. Like, what is the point of ruining all these cities?
Theo
I think they wanted to just. They want us to deteriorate. They want us to have no sense of purpose. Right. They want us to, like, not have any pride in the places where we are because they've been so riddled. They get people addict. You know, the opioid epidemic was put on America and was allowed to occur. Right. They want this.
Kara Connolly
I wasn't like that when I was young. No.
Theo
They want this to happen. It is a. There is. It's no doubt to me that this is an organized agenda.
Kara Connolly
Yeah. I don't get it.
Theo
But I believe that people can fight back, and I believe that.
Kara Connolly
I think it started a little bit.
Theo
I think so, and I hope so. And also, it gives you a sense of purpose in the world. It's like you're here to defeat evil, you know? And we are all can be a part of that. And I think it's something that makes us feel that way. Let's pivot a little. You ended up in the. Oh, Quick question. Did you ever see Irish Mickey Ward? Did you ever run across him when you're running around over there? Did you ever hear about him or anything?
Kara Connolly
Oh, yeah. He's boxer.
Theo
Yeah.
Kara Connolly
Yeah. I never ran across him.
Theo
That's cool.
Kara Connolly
Yeah.
Theo
Yeah. I was just watching the Fighter the other day and that's about him, right? About him, yeah.
Kara Connolly
Wasn't he in it? Didn't he play as the coach?
Theo
Yeah.
Kara Connolly
Something. No, he. I thought they gave him a part.
Theo
He was in it at the end.
Kara Connolly
Okay.
Theo
Christian Bale, Marco.
Kara Connolly
That's when he got all skinny for it. Yeah.
Theo
Such a great movie, but. And all the sisters and stuff. They did such a great job in that film. I got to go to watch Lainey Wilson last night.
Kara Connolly
Oh, that's right. The concert. How was it?
Theo
Yeah, I should have got y' all tickets. I didn't even know we're here.
Kara Connolly
Oh, no good.
Theo
Forgot. That's okay. It was so great. It was so great. Jelly roll was Zaire, so I got to see him. Ella Langley, I got to meet her. She has a beautiful voice. It was just great. It was like a special time.
Kara Connolly
Nice.
Theo
Yeah. And Lainey's just a boss. She's just turned into like a. Some people start to step into whatever gift they were given in the world, and some people kind of meander around the outside of it, I think. And in no way is like a vic is better than the other, really. I think it's all by person. But she has just really embraced this role of just being like this on stage presence. It was really powerful to watch. She does a great job pivoting. Anyway, that's. You ended up in the human trafficking unit?
Kara Connolly
Yes.
Theo
So I have the safe term or how does that work?
Kara Connolly
Yeah, that's. So I was in a district detective at Dorchester and then I went for several years, like five years or so to the human trafficking unit and then I went back to Dorchester. But yes, I had a five year stint in the human trafficking unit as a detective.
Theo
So what. What is your definition of human trafficking? Let's just get that clear. Because you hear so much, right? Like a few years ago, you would hear this social kickball that was big. This was big four years ago. And everybody notices it's gone now, right? Notice how the kickballs fly. It's like, oh, that's the big thing. Everybody's commenting on it online and now it's gone, right? It's really out of the zeitgeist. I know it's still. There's still things happening, but notice how that happens, right? And everybody's like, you'd see memes online. It's like tonight while you sleep, one and a half million children will be taken across trains across America being human trafficked. And you're like, what in the shit, dude? So what did you really see? What were you expecting when you got into that space?
Kara Connolly
So I didn't know. Know like everybody else. I didn't really know what that meant. I just, you know, I knew someone asked me to if I wanted to join the unit. And, you know, I didn't know a lot about it. I thought it was just like the movies, like, you know, people being snatched off the street and forced into. To be processed in. In my experience, at least when I did it, that was not the case. So I guess human trafficking is like when someone's trafficked for the purpose of. To sell sex. Right, against their will through, you know, coercion or force or threats or whatever. But when I got there, a lot of the cases we had, it's funny, there were just several pimps that kind of ran the city that were involved. You always came back to the same, like, six or seven guys who always had all these different women working for them. And it was always girls. Not always. I shouldn't say that. Mostly it was girls from the neighborhood or just outside the city, like the suburbs or whatever. And something in their life, like, was fucked up. Whether it was, you know, a parent situation where they had one parent or they'd been, like, sexually abused as kids themselves. Or there was, like, a dcf, which is Department of Children and Families. Like, there were foster kids. It was always kind of something missing. It could just be they weren't getting attention at home or they weren't happy. And the pimps, a lot of them could be very charming. And they would meet these girls. They'd just meet them in the street, go to the train station. They hang at the tea. At the tea in Boston. Or I had one girl, it was a guy walking, talking to when she was walking down the street, and like, oh, you're pretty. You want to be in a music video? And she's like. She's like a teenage girl. Yeah, that'd be cool. And she went like. They shot the video, and then, like, I say, like, we have to finish the video. And then they, like, make her go to another state and, like, like, oh, we're gonna take pictures of you and put you online and. And you're gonna, you know, have sex with these guys for money. They don't get any of the money. The pimps get all the money. So that was a situation where it was kind of. She was not a lot. She was not willing. Like, that was kind of a quick one, like, over a week or two. But a lot of them, they groomed the girls for a long time. They, oh, you don't have any money. I'll give you some money. I'll take you to get your nails done, honey. I had one guy. I literally had text messages for, like, a month's worth, and you could see him grooming her. She worked in a store. I think her dad. Her mother was deceased, and her dad now wanted to be a woman. And it was, like, fucking with her head. And he, like, changed his name to Susan or something. And then she met this guy working in a store, and he was like. He's like, oh, you're working today, honey. I'll bring you a tuna sandwich, and I don't want you hungry. And it was. You could see it Was like, you know, just progression of a relationship. And like, a month later, she was like, oh, that's my boyfriend. A lot of them think this. This pimp's their boyfriend. And like, a month later, you could see the messages. He's like, all right, we have seven guys coming in. And you know you're gonna do all seven of them at a party. There's like a bachelor party or some shit. And then she's like, can I keep, you know, a hundred bucks for the piggy bank? And he's like, no, it's all mine. It was like a thousand dollars.
Theo
Damn.
Kara Connolly
So it's like. Like they see something missing in their lives and they just manipulate them or they're like. They're a little messed up to begin with. They're like. They're in a bad situation. They don't know how to get out of it. They think these guys are boyfriend, you'll do this if you love me kind of shit.
Theo
So that was a lot of the sex trafficking you saw, huh?
Kara Connolly
Yeah, that's what that was. In my experience, yes. There wasn't a lot of people being snatched off the street. Like, no one's being shipped in in a shipping container from Russia. And all these girls getting, you know, the nail salon, the. The. The spas are a little bit different. The Asian women, they were moving them around. Yeah, but those were tough because the second we try to, like, go in and they move, they're gone. They're gone to New York, New Jersey. Different women, they're gone. They don't know their names. There's, like, how many different dialects have been pronounced. The name Chinese. Trying to get our Chinese officers. Hey, can you translate this? And they're like, it's a different dialect. Like, it was a disaster. So those were. Those were the.
Theo
You're, like, we're looking for.
Kara Connolly
So we did those.
Theo
Yeah. That's crazy. That kind of shit's wild. And I don't like those kind of places. I'll say that. I walk into one of those salons or whatever, I say, if anybody jerks me off, I'm jerking them off. That's what I tell them. No homo.
Kara Connolly
I'm just saying.
Theo
But I'm. You know what I'm saying? I put the pressure on everybody in the building.
Kara Connolly
Just so everyone knows what you're going into.
Theo
Don't even jerk me off. If somebody tries to even sneak up on me and jerk me off.
Kara Connolly
Some of these girls would sleep in there. They would sleep on the beds at.
Theo
Night when they sleep, and then they wake up and jerk you off. That's the problem.
Kara Connolly
But one of them had. We went in one there sink. There were baby turtles in the sink filled with water, swimming around. Like, what the.
Theo
They like the animalia in there. They love aqua animals, a lot of soup.
Kara Connolly
I don't know what the hell they were doing. I don't know what they were doing with those things. We're like, what the. I don't know, you know. And we also did part of the human trafficking and we did John, what we call John stings. We target the sex buyer rather than. That's kind of a. It was a European model that they found to be more effective rather than, you know, cops used to arrest the prostitute. Well, what about the guy paying for it?
Theo
Of course.
Kara Connolly
Yeah. So then you target that angle of it. Like we're gonna tell you if you don't have buyers, then no one's gonna be selling it. They tried to do it kind of backwards that way. So we would do what we call Johnstings and we'd put ads online. Backpage doesn't exist anymore, but we put them on that. It was Craigslist first and then it was Backpage. I don't know how they're doing it now. Whether it's on Insta or, you know, TikTok. I don't know where the hell they're doing now. I've been out of the unit for about six years now.
Theo
You'd have parties and people would find people on Backpage and invite them over, you know, like, yeah, they would hire strippers and stuff like that to come and dance or hang out. So it was definitely a place where people were kind of illicit and illegal.
Kara Connolly
Oh, yeah, that was there.
Theo
Yeah.
Kara Connolly
When you put an ad in, you could pay extra to bump it at the top. So it was so prevalent when we were doing it. Like, we put an ad in the morning, say I put my ad on. We, like three or four of us in the office would do fake ads. And you'd have to do, like real photos. Cause the guys who were doing it all the time, like, we'll do reverse Google Image search to find out did this picture appear someplace else so they know if it's a fake photo. Because then maybe you're a cop, but you're not going to look like who you're pretending you look like. So we'd all put our ads up. And then, you know, you put on at 8, at 8:30, your phone's ringing. It's crazy. 8:30 in the morning, they're Already starting to call. And we'd set up our dates for the day. Like, we'd have a hotel room, and we'd be waiting in the hotel room, and we'd have dates set up every half an hour to show up.
Theo
And will y' all hide under the bed? Bed?
Kara Connolly
No, no, it's hiding on the bed. I would have to open the door, and. And there'd be, like, guys, like, in the bathroom, Officers in the bathroom behind the wall. So I. My trick was. And I was at, like, 45, 46 when I was doing it. And my Adam's supposed to be 34. I didn't look 34, but I opened the door, I'd have, like, my hand.
Theo
Would be the girl.
Kara Connolly
Oh, I was a prostitute. Yeah.
Theo
What?
Kara Connolly
Yeah.
Theo
What were you.
Kara Connolly
So I have to talk to them on the phone.
Theo
Were we all understaffed or something? They just shouldn't have you also the detention to have.
Kara Connolly
You're the one establishing probable cause. So if someone else is doing it, and then you have to, like, go testify in court. Well, you're not the one that had the interaction with them. So what we do, we put our ad online. You'd put your photos and some stupid saying, like, you know, what you're offering and how much it costs, and it causes acronyms for everything. That's what. I didn't know anything about this before I started about gfe, which is girlfriend experience, which means she'll kiss you full service. Means, like, sex and a blow job. And then there's, like, Russian and Greek, and there's all these stupid acronyms for everything else. And they. They thought they were being clever by saying, oh, I want gfe. So they're not asking for sex.
Theo
Oh, I see.
Kara Connolly
So by them saying I want GFE or I want Russian or I want this, they think they're being clever. Except you can say, like. Well, based on my training experience, I know Russian means titty job, like, or whatever. And then. So you talk. They call you on the phone.
Theo
Titty job.
Kara Connolly
Yeah. That's a Russian, by the way. I didn't know that.
Theo
I'll take it. I mean, whatever they're giving, you know, I mean, it is. I'm sorry. Yeah, that's okay.
Kara Connolly
So you'd. You'd basically talk to them on the phone. They call you, and some of them are real nervous. Obviously, you could tell the long time or say, you got right to business. And some of them want to flirt with you on the phone or whatever. Can you send pictures of your eyes or your feet? The foot fetish guys are out there big time, but. And then you're like, the more you do it, I'm like, I don't have time for this shit. Like, do you want to come? You know, we showing up or not? So you'd basically make the arrangement. So once they showed up, you already had probable cause. They always already agreed to pay you for sex before they ever showed up. So then by them showing up at the hotel, they're like basically completing the entire. The elements of the crime. They showed up, they already agreed to pay you for such and such. So then you can arrest them right.
Theo
When they get there. Really?
Kara Connolly
Yeah. But like, depending on where we do it, if we did it, like nights or downtown parts of the high end hotels would let us use their rooms. Oh, yeah, give us a high or whatever.
Theo
You do anything in there?
Kara Connolly
Every time we did it, we got a doctor. Every fucking time. The Brigham Hospital, one of the best hospitals in the world. Allegedly. The Beth Israel one. Guy showed up in scrubs with like Beth Israel Hospital on it. Yeah, like, what the fuck? You on lunch break? It was crazy. We got doctor every time.
Theo
Why you think?
Kara Connolly
I don't know. Too busy. Too busy to get a girlfriend? I don't know. That could be it.
Theo
Yeah. I wonder what that is.
Kara Connolly
That's just fantastic. I don't know. It was. We always got. And when we did it in like the not so nice parts of town, then we'd get like, you know, the cable guys and the plasterers. And for some reason I always felt bad for them. They didn't have any money, but it's the same crime, so I shouldn't have felt bad for them. They were just, you know. But I did the rich guys. Cause they got very arrogant when you tried to arrest them. They were all arrogant. We had one guy who's a Northeastern University professor, and he was on the phone with me saying, I'm a professor. And he was trying to talk me down on my prices. I don't make a lot of money.
Theo
That's what I would do. I would text him, like, look, how about this $70. Some lady's coming over for $70. I'm like, Jesus. And now I'm like. Like I would.
Kara Connolly
He was bargaining with me. I don't make a lot of money. Meanwhile, I made more money than me.
Theo
Yeah.
Kara Connolly
But he. I always laugh. He wanted me. He's like, will you put me in yoga positions? That's what he wanted. He's freaks. I'm like, yeah, I got my Lulu's On. Come on over. Like, you just. He wanted to be in yoga positions, me to put him in them. And then aggressive kissing.
Theo
And when you get some weird requests or anything like that. Yeah, like, look. Anything. Pretty wild. Like, were they any, like, people you to enjoy them and their wife, like, join, stuff like that?
Kara Connolly
No, nothing. We never got those. We got a lot of. Almost everybody was married. One of them, we did. We met him in a bar. He said it was the end of the night. He was too nervous to come to a hotel. He said he'd never done this before or whatever. So we agreed to meet him downstairs at the hotel. Had a bar downstairs. And we. I was just sitting there. And now, again, I'm supposed to be 34. And even 10 years ago, I didn't look 34.
Theo
I think you look great.
Kara Connolly
I look 34, but. Thank you, but. So I'm sitting at the bar waiting, and the signal is for, like, me to touch my hair. And there's two cops down the end of the bar. And he comes in. I see him walk past. He comes in. The bar is crowded. I see this guy walk in. I said, that's him. I knew it was him. You could tell. Like, his face was. He was. He wasn't like, hey, I just got to a bar, and he's all chilled. He was, like, intense. And he walked right past me and went to the men's room, looked at them like, that's him. He's got his fucking Burberry scarf on and his, you know, $400 jacket. And he came over and approached me, a librarian. He tapped me and, you know, said, oh, my name or whatever. And then when they came up to arrest him, he fainted. We had so many guys faint or, like, collapse on the bed. He's. He went. His face, he was white as a ghost. And he just went down. So the officers, like, drag him out to the vestibule, the bar were like, we gotta call this guy an ambulance. But he. He snapped too. And he's crying and. And he's like, oh, he's like 30 years old. Like, dude. He's like, I'm so anxious all the time. I. I'm trying to get my wife pregnant. And I was like, you think you're gonna get her pregnant by a prostitute? Like, what is wrong with you?
Theo
I mean, it's worth a shot. You know what I'm saying?
Kara Connolly
I'm not saying you go a stranger and they. None of them. Nobody wants to use a condom. That was bareback. That was another code.
Theo
Oh, they were Doing.
Kara Connolly
Yeah, that was a code. Bbbjs Bareback. Bareback. So they. They didn't want to. Oh, there you go. Here you go.
Theo
Bareback. Sex without condom.
Kara Connolly
Yeah.
Theo
Bbb.
Kara Connolly
And they'll ask you how much extra? Like, how much will you charge me for a bareback? So none of them wanted to use a condom. So they're all going home to their families after fucking some rando who's got. Having sex with five people that day.
Theo
Yeah.
Kara Connolly
Like, how many diseases, not to mention.
Theo
In what township is it in?
Kara Connolly
Just Boston.
Theo
Yeah. Oh, yeah.
Kara Connolly
So this guy's bringing the. Oh, I'm trying to get my wife pregnant. What are you bringing home? Yeah, bottom bitch. That's the pimp's main. Main girl. She's the one who runs it for him. I see that in the terminology. Yeah.
Theo
Let's see some more terms here. The in call. Yes.
Kara Connolly
That's only b. See, they go on forever, huh? Yeah.
Theo
And where people ever asked. So I'm trying to think of anything people are asking for, like golden showers, urination type of thing.
Kara Connolly
I never had. I never got asked for those. One thing they asked you for, the guy's like, will you do a handy? And I'm like, was that a quick hand job? Like, I had no idea what the it was. And my partner at the time is like, googling on the urban dictionary. Like, what's that? It was some crazy thing about choking and she's on top, and then you flip and he's on. I was like, how the. Do they come up with these names? Like, what does that even mean?
Theo
That's all that Cirque du Soleil shit people are doing.
Kara Connolly
Like, how is that a handy? Because I was like, is that. Like, what is that?
Theo
That's all that welterweight stuff, I think. I don't know what it is. What about. Was there a lot of stuff? Like people want you to touch the. Their. The hole in their butt or anything like that? Like, any weird stuff?
Kara Connolly
No, they never got that specific on the phone. But they would ask for anal. That was Greek. They were like, we do one of them the clever way. They're like, oh, do you speak any languages? So then I'm supposed to say, yeah, I speak Greek and Russian. That's what I mean. They think they're clever. They have all these weird online forms where they talk about the prostitutes. They rate them. I forget what the page they used to rate them on. So that's why we had to change up our photos and use real stuff because these guys all talk to each other. The long. The guys that do it all the time.
Theo
Time.
Kara Connolly
Not the one timers.
Theo
The lifers.
Kara Connolly
Yes. Or dabblers like yourself.
Theo
Dabblers, yeah. In and out. In and out. In and out.
Kara Connolly
Yeah. They talk to each other and rate the girls. It's crazy. It's a crazy life.
Theo
And when would a night like that for you guys end? Like, was there a certain point where you guys.
Kara Connolly
Yeah, we kind of call it. So, like, the calls would start coming in the morning, and we'd, like. We'd have, you know, higher overtime to transport all because they'd be showing up. Sometimes they show up at the same time, like, oh. And they come into the same room. So we try to stagger the dates. Dates. And we have them schedule the area hour every half hour, whatever. And after, like, eight or 10 hours, the boss would call it. We always did a Super bowl weekend. It was Cook county in Illinois, did a big funding thing for it. They got money from the feds, and they all kind of agreed to do it. So at certain times a year, Super Bowls were always when we did it. So we call it a night after, like, eight. After we arrested, like, 12, 14 people or whatever. She'd be like, all right, that's enough.
Theo
Enough. Like, so on super bowl weekend, you guys are so. So.
Kara Connolly
Yeah.
Theo
So on most super bowl weekends, you guys are doing that.
Kara Connolly
We were. When we're in the human trafficking unit. Yeah, but it's. We got one guy. He was. He was. I was talking to him on the phone. I'm like, this guy is so old now. I'm laughing. I was very shy about it when I first started doing it. I don't know who the hell. I'm not a prostitute. I don't talk to these people. So I'd be all anxious, like, hiding in the bathroom. So there's this eight cops in there. I don't want them listening to me. Like, yeah, you can stick in my house for an extra 50. Like, I was embarrassed. And then I got more comfortable. And they would just be laughing. Like, I'd just be like, yeah, this is what you want. Okay. And everybody's laughing. One guy.
Theo
Yeah, come on. My four old.
Kara Connolly
Whatever for 30 bucks sounded so old. And he's like, you gotta. You know. Yeah. You know, I'm an older gentleman. And I remember saying, that's all right. I'll take it easy on you. And then he shows up. He's, like, shorter than me. Turns out he's, like, multimillionaire philanthropist from Beacon Hill on the boards of, like, Children's hospital and all this crazy. He laughed. He burst out laughing when he got arrested. He was a tiny little guy with glasses. He laughed. Everyone else shits himself or gets angry, but he laughed. He's the only one. He didn't give a shit. He's like, yeah, I'll pay the fine. I don't care. Just get my phone back. We take all their phones. And I remember I was doing a detail at Fenway park and he was in contact. He's like, I paid my fine. Can I get my phone back? Because we take their phones as evidence. We have to show their text messages or whatever. And if they plead, pay the fine or plead out, they get their property back because the case is, is done. But if they're fighting it, then we keep the evidence because we have to do a search warrant on the phone and all this stuff. He's like, yeah, I paid my fine. He literally, he showed up at the Red. I'm like, I'm working in detail. Like, you can come and get it. So I was in uniform that day because normally I'm not in uniform. And he showed up and he's laughing in the car. I'm like, here's your phone. I'm like, what's the matter with you? Like, why don't we got money? Go get a girlfriend. He's like, ah, see, it's not worth the trouble. I was like, all right, have a good day. He did not give a shit.
Theo
Wow.
Kara Connolly
Yeah.
Theo
Gosh, dude, did you, did you ever just like accidentally just hook up with one of them? Like, did that ever happen?
Kara Connolly
No, no, that didn't happen.
Theo
Like, did one of her show up and you're like, oh, this guy's kind of cute? I wish it wasn't like this.
Kara Connolly
No, I never thought. I wish it wasn't like this. But yeah, some of them weren't. You know, that's what we say. Some of them are good looking. You're like, what's go get. What's wrong with you? Like, you're a good look. We used to say, like, you're a good looking dude, you can get a girlfriend. Some of them are like, like grotesque. Like, you could see why they're paying for it. Like I said, the doctors don't have time. Maybe, I don't know, they don't want the commitment. But some of them be good looking dudes. Like, what's wrong with you?
Theo
I think for some guys, they, they have a. Their sexual experience, especially if it starts off with pornography. A lot of times is really.
Kara Connolly
Well, that's an issue now. They don't know what's real life, you know.
Theo
Right. But they don't. But then it's if, say, like, you know, if it starts off with pornography, it's very skewed, right? Because this is a. An environment that's kind of like you can get exactly what you want out of pornography, is put the terms in, you get what you want, and that's your intimacy. So that's how you build it. Right? So then it almost makes. It doesn't. It's not Right. Doesn't make anything right or anything like that. And some people, you know, like, prostitution is one of the oldest businesses in the universe, right? It's always been there. But some people, they. The next. The closest way they can get somebody is almost just trying to create the same thing, but in real life, right? So, like, I need to create the same thing where it's like I can kind of get what I would like.
Kara Connolly
Like, yeah.
Theo
These are my Google terms. These are the things that I like, and I'm gonna pay for that.
Kara Connolly
They don't want to waste time maybe. I don't know.
Theo
Oh, I think some people, for sure, it's time. It's like, I don't want to have a big relationship. I just want to have.
Kara Connolly
I don't want to take someone out to dinner every, you know, twice a week and spend hundreds.
Theo
And there's a lot of that that goes on, and I don't look down upon any of it. I just think it's. It's interesting that, you know. But, yeah, the laws are the laws and those. And that's just what your experience was like.
Kara Connolly
Yeah. So what I learned, like, I, you know, it's like, hey, if a girl wants to do it, but in reality, I think 99% of the time, they're not making a dime, so they're doing it all, and the pimp's taking all the money. So that's why I was like, well, that sucks. Like, I had, like, one girl who was like, no, this is how much I make. And she does. But something called sissy play. And I was like, what's. Guys who, like, want. Not want to get hurt, but close to not like sadomasochism or whatever, but she made a lot of money. She's like, I make, you know, $500 an hour or whatever.
Theo
That's weirdo.
Kara Connolly
Guys, you know me, my partner would be like, we need to do job retire. Like, what the hell?
Theo
I know a dude like that.
Kara Connolly
She kept her own money, but literally out of everyone else I ever met, they didn't, they didn't keep it. They had to hand it over. So guys think when we try to do it as like an education thing, we tell the guys when we rest them, like, we're not doing this to hurt because they're always like, don't tell my wife. Like, everyone would panic, say, look, it's kind of was supposedly at the time like an education thing. We're trying to make you aware these girls, you think it's. You're doing something and you're paying for the service, they're giving you the service and everyone leaves happy. But the girls weren't getting the money. They were getting the kicked out of them half the time.
Theo
That's heartbreaking.
Kara Connolly
So.
Theo
Oh yeah, happy stuff.
Kara Connolly
I hated telling people I worked there because it was like a conversation killer. Like you'd see people's shoulders just droop. You're like, oh, you work at the improv unit. Like, oh. So you know. Well, I'm sure nothing good there. Nothing good happened in there.
Theo
Well, it's just interesting how perverse like sexuality can get and the things that cause it in our world. You know, it's another thing why they even allow pornography to exist. Like, I don't know if we need it, like as readily available as it is. We had a woman come on named Lila McElwait and she was telling us that a lot of the pornography you see online, it's non consensual. Right. And so a lot of times you could have somebody basically masturbating or watching and, and enjoying a crime and they don't even know it.
Kara Connolly
They don't know.
Theo
Just the whole circle of it all is kind of depraved. But then I, I have friends that do sex work and they work for themselves and, and they're masterful at it.
Kara Connolly
Fair enough. If they're, if they're working for themselves and they want to do that and they're making the money, that is victimless.
Theo
Yeah. And I think. And people may have issues with people on both sides of the transaction. Probably have some issues and may or may not. It could be different. But. But anyway, yeah, that would just be. But yeah, some people are in a weird stuff. I had a buddy, he would hire a woman just to tickle him until he himself.
Kara Connolly
Oh, this is some weird out there. There's a lot of fetishes, man. That's why I found out about. I started putting my feet in the photos because I was like, I got to get the foot fetish guys. Yeah, yeah, because people want some. Like the guy wanted me to put him in yoga positions. How does that do it for you? Yeah, it's bizarre. Like you said the guy wanted to tickle till he got till the. Yeah, that's a really specific wish.
Theo
Oh, if you tickle like how do you get there?
Kara Connolly
Yeah, how do you get there? And go like, were you tickled as a kid? And we're like, oh no, I'm gonna myself. And then as adult, that's what it does it for you probably.
Theo
I don't know where you watch a funny movie and then you have to pee. Like maybe. I don't know, I don't know how you start.
Kara Connolly
I don't know how you get there.
Theo
But yeah, if somebody tickled me to last, I would be upset.
Kara Connolly
Right.
Theo
I think overall, I think most would. Did you ever feel like you were had to be like a protector for these women? Or did a lot of them feel like they just, they were in their own space and that's what they wanted and it's not something you can really help with. Like a lot of the women, there's.
Kara Connolly
A lot of case. It was a lot of. I feel like you're just banging the head off the wall going nowhere. You help somebody get them and you get them away from somebody, you get them into. It's like a safe home. Like there was a woman who ran a non profit a place to put these people, get them some clothes. Like a lot of them, they'd steal their shoes and their IDs and their phones or whatever so they couldn't run away. So you find them a place to stay and you know, get them Target gift cards so they can go buy like a toothbrush and some soap. And then like the middle of the night they jump out the fucking window. So like you do, you're like getting called out of your house at 10 o' clock at night to go help somebody and then they're like, oh well she's gone. And so many of them ended that way or they just disappeared. They wouldn't testify against them. So the cases went nowhere. So it was a little frustrating.
Theo
Yeah, I think it's people. You can't help people till they are ready for some help.
Kara Connolly
Exactly, yeah.
Theo
Did you. What about any, was there any gay active. Was there any gay pimps out there? Was that that kind of thing?
Kara Connolly
I don't know.
Theo
A guy ever lie and say like when you busted him, like if, like say you set him up with a female prostitute and he, he just like he's like, I'm gay. I'm just joking. You know, happy Halloween or whatever.
Kara Connolly
You know, they never tried that. I mean, the jigs up, as soon as they show up. Most of them knew it. They like fall on the bed. A couple of them cry. Like, really?
Theo
Yeah.
Kara Connolly
But no, none of them, no one ever tried to show the gay card. Be like, it wasn't me. I'm just here for fun.
Theo
Yeah, I'm just, I was just joking with you.
Kara Connolly
Yeah.
Theo
You, you had a, you had an investigate. You had a three year investigation that you worked on.
Kara Connolly
Yeah, that was a human trafficking case that I did with someone from Homeland Security Investigations.
Theo
Okay, and what was that like? Take me through some of that story. You had a three year investigation that.
Kara Connolly
Actually started with the one I told you, the girl, the music video.
Theo
Okay.
Kara Connolly
That's how it started. And we, we got a call to Children's from Children's Hospital in Boston saying this girl there said she was raped in Rhode Island. I think she was 15, maybe or 16. That's how that case started. And then we found out all she had was a nickname. Wasn't even Guy's real name. She had like his Facebook page and.
Theo
A nickname like Smokey or something.
Kara Connolly
Yeah, I don't want to say it.
Theo
Okay, sorry, nevermind.
Kara Connolly
No, the guy.
Theo
Yeah, I was just guessing if it.
Kara Connolly
Was Smokey, it wasn't Smokey. So she all shares a nickname and we kind of worked backwards from that. Like, one of the Homeland Security agents drove the girl. She's like, oh, this woman drove me to Rhode island, but she wasn't involved, but she drove me. And this is where she lived. She lived in this neighborhood. That's where I had to meet her. So the Homeland Security guy started driving around and he saw the car in the neighborhood and got the license plate. So then I start looking on my end because he doesn't have access to Boston police reports. I start looking for the license plate and a car that matches her description because we don't know if it's exact. And I find a car, but it's a guy's name. But then I start looking for reports with someone for that last name. And then I found a woman with that last name and with her first name because she told me the girl's. She knew the woman's first name. All we had was a first name and a red car. So then I find the last name in the car registration. I find old reports with this woman with their first name and the same last name. And we're like, oh, shit. That we pull up the. You know, we did a photo raid, show the girl, and she's like, that's her. So then we start talking to her and we end up going. It was like a spider web. So these two guys. There were two guys who pimped her out in Rhode Island. But she did get raped by some guy. The guy in Rhode Island. I got like seven years for the rape or something, because she did not go willingly. And those two guys worked for another pimp. And he had women all. I think he was in his late 20s and he had, I think, like 11 baby mamas and like 17 kids or 14 kids, something crazy. But he had like 27, 28 victims. Girls that worked for him over a period of time, including a bottom bitch. She's like the girl that works for him who recruits girls and is basically in charge of everything, collecting the money, whatever. She works herself too, usually the bottom bitch. But that took like three years because we were like, in Maine, New York. These girls went to New Jersey, they went to Vegas, California. They would drive. They would drive to Vegas and work and then drive back. But he had all these women working from. And he was very, very violent. Like, he would beat the shit out of the girls. He would pee on them, stole their shoes, their licenses, their cell phones so they couldn't call home. Like, like I said, some of these girls came from, like, messed up places. And it took like three years to get enough people to. Because every time we found somebody, we found somebody else. Yeah. So that took a long time. But that was. That was. He was. He was. I think he got like 33 years in jail because that went federal because of all the different states. That was a biggie.
Theo
Well, thank you for that. Thank you for that work. Thanks.
Kara Connolly
I liked going back to the district. I mean, I liked it at the time the schedule worked. But the district is great. People like the patrolman. Because when you were in the human trafficking, there's no patrolman. It's just detectives. So it's like four or five detectives and a supervisor. When you go back to the district, there's, you know, 100, 200 people there, so it's a lot more fun.
Theo
Yeah, you're part of life.
Kara Connolly
We laugh all day and stuff like that. So I was happy.
Theo
I realized that kind of stuff. I go hang out with the football team around here sometimes, and it's just like some of the best parts of my week. Because there's just people around.
Kara Connolly
Yeah. And you can't, like.
Theo
Otherwise my life is Very much like kind of by myself. Not by myself, but it's a limited amount, you know.
Kara Connolly
Yeah. It got old. And again, all the cases, most of them go nowhere, so that's frustrating. And I just wanted to go, you know, back to the district and it's great people, they're the best people on earth and you just had laugh all day, you know, like when it's real shitty. Like the one with the guy, you know, two women stabbed and the dog was stabbed in the stomach or whatever. Like, those are like. We work with really good people.
Theo
We're all there together.
Kara Connolly
Yeah.
Theo
Yeah. And you. And you won detective of the year for that, right?
Kara Connolly
Yeah, for the federal mess. For the three year. Yeah.
Theo
Let's go, Kara. Congratulations.
Kara Connolly
It's funny, you know, Mark Wahlberg was at the ceremony for the Boston Police foundation gave me the award. The detectives union did too, but the Boston Police foundation did. It's like a non profit and at the time they were promoting the movie Patriots Day and Peter Berg, the director and Mark Wahlberg were there for the award ceremony, gave me a picture with them or whatever.
Theo
You did. Yeah, that's cool. I'm gonna have to. I will.
Kara Connolly
Yeah, they were. They were promoting that.
Theo
I'll text Mark and send him our picture. I don't know if. He probably doesn't even know who I am, but I think I accidentally snuck his number off of a sheet one time.
Kara Connolly
Mark Wahlberg.
Theo
Yeah.
Kara Connolly
Yeah. Cause he's from Dorchester, where I was a.
Theo
Yes. Oh, then I'll make sure that's where.
Kara Connolly
He and his brothers, the family's from.
Theo
Not even in a braggy way. I'll just be like, hey, this is awesome. I just wanted to let you know I met one of Dorchester's finest today right here. But congratulations. That's so cool. Did that make you feel a sense of accomplishment?
Kara Connolly
Yeah, I mean, I worked hard. Again, it was with Homeland Security and a Homeland Security agent. She did a shit ton of work, more than me. She was great. We worked together on it. And like I said, it was a long. It was a long investigation, so I was very happy to be. Have it resolved, you know.
Theo
Yeah.
Kara Connolly
In the process of it, someone, the pimp who was in charge, who thought the first two pimps that got caught with a girl in Rhode island that I found through a nickname or whatever, they thought one of them was rat into the feds. So he had someone shoot one of them in the head. No, he lived, but not good. It was like a piece of pie was missing from his head and he Just. He could sing, but he couldn't talk. He could no longer speak. That's when I found out they said in the brain, like, oh, it's different parts of the brain. He could, like, single the Alphabet and happy birthday, but he couldn't speak. Oh, and he was not rat into the feds. He was nobody. He was like, away in New Jersey with some girl.
Theo
Not at that point. You're like, who did? And he's like, D, E, F, G. Yeah, I got.
Kara Connolly
I was in court on something else, and one of the DA's. Did you hear this guy got shot? And I was like, what's his name? I was like, oh, shit, that's. We're looking for him. We have an arrest warrant for him. But that guy had him shot.
Theo
Man. To get caught up in such depths of darkness. Yeah.
Kara Connolly
Yeah. So that was. I was glad to be done with that one.
Theo
Is most of your social life with. With police officers and cops and stuff? It is.
Kara Connolly
It was until I moved.
Theo
Move where?
Kara Connolly
I moved out of Boston. I moved to South Carolina.
Theo
You did?
Kara Connolly
Yes.
Theo
No way. What part do you live in?
Kara Connolly
Yeah, I live just outside of Charleston, dude.
Theo
I used to go to College of Charleston for one semester.
Kara Connolly
Nice.
Theo
Yeah, I used to live over on King street above a buddy's apartment for a while.
Kara Connolly
King Street's the shit.
Theo
It was pretty neat. It was a little bit different, but it was. Was fun. And it's beautiful over there.
Kara Connolly
It's gorgeous. And I don't want to be cold, so. And I'm not a Florida person.
Theo
And your daughter lives over there?
Kara Connolly
Yeah.
Theo
You guys got Folly Beach? That's right there?
Kara Connolly
Yeah. Iop Palm. Sullivan's Island. Yeah, but they. She. She lives. No, we live north of. Just north of Charleston. So, yeah, we moved there. So right before I moved. Forget where we're going with this.
Theo
What was I saying? Is most of your social life.
Kara Connolly
Oh, yeah, yeah, yeah. Until I moved. Yes. And it's weird. Everyone's like, oh, you gotta have friends that aren't cops. So I have friends that I'm still friends with from high school, that I've been friends with for 40 years. So I have a core group of girls, a few girls that I've known since high school. But it's weird when you become a cop. Like, it's hard to talk to regular people. Only because I always said I felt like a party trick if you're out in a large group and someone's like, oh, they're a cop. You got any stories? Did you ever shoot anybody? No, I Didn't fucking shoot anybody. And if I did, it was a bad day. So maybe I don't want to talk about it. So I think that's why we all just end up hanging together. Because we get it. Whether it's, you know, cops or nurses or whatever. Yeah, they get it. Because you don't want to feel. You don't. You don't want to be performing all the time. Like, I don't want to talk about it. Sucks.
Theo
Yeah.
Kara Connolly
Some of it's funny.
Theo
Just handcuff sex jokes, you know, like.
Kara Connolly
Dick on the sidewalk sounds funny. But that was a sock morning. You know what I mean? More for that kid than me. But in baby in a trash can can and all this other. It's hard.
Theo
Yeah. First of all, a lot of these sound like. Like, a lot of these sound like baby shower party games, too.
Kara Connolly
I do want to say that.
Theo
And that's not what we're doing here today, guys. It's just kind of some of the way things sound.
Kara Connolly
Yes. That's. Those are my. What I call my chapter. My titles of my chapters of the alleged book I'm going to write. That's why I shortened it like that. But, like, you don't want to feel like you're on all the time. So that's why we hang together. Because we all get it. And we have weird sense of humor. We're different. Different people. Like, when we have Christmas, I run the. I used to run the Christmas parties for our district. And they'd be like, oh, we can section off a part of the bar. We're like, no, no, no, no. We have to be in our own space. Like, we are not fit for public society. I used to say. Because we say shit that is not funny. And if it's funny to us, but if, like, random normal people who just go about their business heard some of the shit that we'd say, they'd be horrified.
Theo
Oh, I've had very recent experience with some of that. And I feel you 100%. Wow. Was it hard to move away then?
Kara Connolly
No, I was ready.
Theo
You were?
Kara Connolly
Yeah, I was done. And I wanted to be warm. My daughter was already down here, so.
Theo
Oh, your daughter lives in Charleston?
Kara Connolly
Yeah. So I was. So I wanted to come down.
Theo
Is that your only child?
Kara Connolly
Yeah.
Theo
Oh, she's beautiful.
Kara Connolly
Thank you.
Theo
And are you still married or.
Kara Connolly
No, no divorce years. Yeah.
Theo
And was that harder? Is it hard to keep them do. Are a lot of officers married? And is there a lot of dating on the force? What's it. What's that? Kind of life like for. It's a little, it seems very spend.
Kara Connolly
A lot of time together. So there's always a lot of relationships form in the police department. Like cops end up married to each other. I'm divorced. I've been divorced for years. It's funny, my ex husband and his new he's remarried wife, they moved down here too.
Theo
Oh, nice.
Kara Connolly
Yeah, so we all get along. So they. So they could be near my daughter and they have a child as well. So she has, she has a brother with him. But it's hard. It seems easier now for some reason. Cops now, in my experience that I've seen, are more family oriented than they were when I was young. There was a lot more drinking going on then like guys would stay late in the parking lot and like no one would go home. And now everyone's all about their family. So I think it's morphed whether it's who they're choosing or who wants. No one wants the job. First of all, by the way, when I took the police exam, like 10,000 people took it. And now they can't even get like 800 people to take the test. No one wants. I mean, it's terrible.
Theo
People hate us, of course, when your district attorney's not supporting you, when your government isn't supporting.
Kara Connolly
And all over the country, like, no, we're not the fire department, everyone, America's heroes. It's a joke. We laugh that no one wants to see us coming. And it's just gotten worse and worse over time because we're not politically supported, even nationally or weren't in the past. It's changed. So it's hard to maintain relationships. Like unless because we're with each other, we all work 12, 14, 16 hours a day.
Theo
I can't even imagine.
Kara Connolly
And so that's how a lot of them end up together, I think. And then again, because they understand it. It's hard for a non police person to understand what's going through our crazy heads because we're all crazy. And we wouldn't take, we wouldn't have taken the job, I think, if it didn't make you crazy.
Theo
I can't even imagine you have to drive in a car that has a siren on it. First of all, sometimes it's kind of aggravating. And then when you get there, you might have to shoot somebody or get shot. Yeah, I'm out. Yeah, it's a lot, you know.
Kara Connolly
You know, it can be. So it's a lot for a regular person to live with someone who's who's dealing with that? I think.
Theo
Yeah. Is it hard to keep the work at work for a lot of people or is it not. Is it.
Kara Connolly
I. It changed. I mean, it varies by person. Some people can shut it off, they don't give a shit, just go home and shut it off. And some people get really, you know, up over it and drink too much or they're too, you know, mental, like, like depression or whatever.
Theo
So what did you think about Trump utilizing the National Guard to help out in some of these.
Kara Connolly
Great.
Theo
I did too.
Kara Connolly
I mean, if the mayor's aren't going to fix it, you can't have that much chaos in the streets. Do something.
Theo
I agree.
Kara Connolly
The fact that they're fighting it, like, oh, how dare you clean up my city. Are you insane?
Theo
I would love if there's military and I mean, like, especially if it helps us get to a point where we don't need that, where there's a bit of there, you know, where it solves the people wanted.
Kara Connolly
It's funny, when everyone was hating on us a few years ago, bad after George, Floyd and stuff, everyone hate us. Videotaping you. Everywhere you go, cameras, every, every radio call you're at, the phone's out in your face. They're waiting for something to happen and they're cursing at you, spitting on like, they spit on you when they talk. And that's not. And you can't react to that. You can't be like, you know, you can't get into it with people. And so we're what pieces of. Yeah.
Theo
Do that?
Kara Connolly
Everyone that's who does it. Everyone, Every piece of. Does it. But then you find out, like, the normal people in the neighborhood, they want us there. They come out, they're like, thank you. Thank you for coming. But that's doesn't happen as often as you'd like.
Theo
And it is interesting. It is like, you know, I think it is a nice reminder to find ways to stop by our police and fire departments and be supportive. You know, one thing that's kind of fun about fire departments, I'll say is you can walk by and see the guys right there sometimes right by the truck, you know what I'm saying? So you can go up and say, hey, you can go up and like, yeah.
Kara Connolly
It's not like walking into a police station. Right.
Theo
Yeah. There you like, okay, well, it just.
Kara Connolly
Has to be secure because there's prisoners inside and there's firearms. So.
Theo
That's true. It's different.
Kara Connolly
Can't be as open and welcoming at.
Theo
A Fire department is just a crock pot full of freaking ballpark franks going on. So it's a different. Now they'll guard those with their life.
Kara Connolly
Some of those guys, different atmosphere.
Theo
Yeah. And yeah, and there's the one guy that's like afraid to slide down the pole. He just waits. Everybody else goes and then he just takes the stairs real fast. But it's none of that's any judgment. These guys are heroes. But that's one thing that's nice. Like we're in New York the other day and they were even doing a call and we like took my buddy's son up and he, he like will wear his little fire jacket around town and he'll just like go get into the fire truck and like they come back and we're just like, this kid's just in their truck.
Kara Connolly
But no, kids love fire trucks. I mean that's, you know, and cruisers, they like the noise. The noise and the lights.
Theo
It's exciting.
Kara Connolly
They think it's cool, you know.
Theo
Oh, wow. Oh, look at this. Here we go. Sean Diddy Combs sentencing live updates comes, gets 50 months in prison.
Kara Connolly
That's actually not that much.
Theo
Four years for his conviction on two prostitution related offenses. What were the offenses? Can you let me know?
Kara Connolly
He must have been sex trafficking of a minor.
Theo
Maybe the most. He got acquitted of the most serious charges. Faced racketeering, conspiracy and sex trafficking. Found him guilty on two counts of transportation to engage in prostitution. You know, I personally thought that this whole thing was something they were trying to create during the election of kind of like. I don't know how they were trying to use it, but I thought it was.
Kara Connolly
They were trying did some crazy shit.
Theo
Oh, for sure. I mean, but do you think he was just a freak that got really addicted to what he was doing and a power like a power hungry. From what I hear, he's a very power controlling type of person.
Kara Connolly
Yeah. I mean, I obviously don't know the gist of the cases why they charge him with conspiracy and sex trafficking with their minors involved helped. So I don't know why. Yeah. So we got what, just over four years. I don't know what he. I mean you can't get them for sex parties, so there's obviously something there.
Theo
That's a good point. And who knows what they kept back. Who knows what got like behind closed doors?
Kara Connolly
Yeah, yeah. Victims don't want to testify. Was he the one with the girl who's kicking the out of in the hallway at the elevator? That was pretty bad to watch.
Theo
Yeah. Never mind. You know what? That give him 10 more years. I am, I'm sorry. I, I. And you know what's messed up? I forgot about that.
Kara Connolly
Yeah.
Theo
You know, there's so much evil out there.
Kara Connolly
Sometimes it's non stop. Every week there's something else. Every day something else comes out. So.
Theo
But do you think. Okay, so going back to that. So that statement, and I agree with it, is a lot. But if we go back to like working the beats on the indoor chest when you were starting, like there's a better way to do it, right? There's a better way we can be.
Kara Connolly
Yeah. People have to be human beings. But there's a lot of people that aren't. There's pieces of shit for whatever reason, whether it's poverty or their upbringing or drugs mess the fucks up families to no one. So I don't know, I don't know what the answer is. It's not what we're doing.
Theo
Right. I wonder if it's what we are doing or what is being done to us that's having more of an effect on us or, or, or probably some, some.
Kara Connolly
Well, yeah. When we can't control it, people are going to be pieces of and bad. Like that's not our fault. That's not your fault. We didn't do anything. We're just going about our business, having a job, getting up in the morning, going to work or whatever.
Theo
Yeah.
Kara Connolly
The people that choose to. I'm just gonna rob this person. Some people are just bad people.
Theo
Yeah.
Kara Connolly
Some people end up that way because the way they're raised. And some people are just bad.
Theo
They really are just the way they are. Yeah. And I think sometimes we do get caught in this space of like oh, we have to react to recuperate everybody and we gotta save everybody. Right.
Kara Connolly
There's real victims out there, right. It's not them, it's not those guys.
Theo
That's a good point. Oh, when it came to the prostitute, the, the john, the pimps and everything like that. Is there a certain like ethnicity, like is it Asian, is it black, is it white, Is it, do you hear like a sir, is that a, is that whole universe of a certain world like where a lot of these. Because you always hear like Asian prostitutes, like was it a certain or is it anybody?
Kara Connolly
So the spot were Asian, their pimps were Asian. But the ones in my experience, in all of my cases, whether they were male or female pimps, because we had a couple females, they were, they were black, they're African American.
Theo
Really Black female pimps too.
Kara Connolly
They worked. Yes. They ended up like the bottom bitch. They end up kind of working on their own.
Theo
The most common ethnicities of pimps in the United States, according to available arrest data and research, are predominantly black, African American, making up about two thirds of identified or arrested pimps. Wow. Followed by a smaller proportion of. Of Latino, white, multiracial, mixed people. They'll do. They'll pretty much do anything. And Asian individuals.
Kara Connolly
Yeah. The spas were the guys. People running those were Asian.
Theo
That's kind of crazy. I wonder. Well, maybe it has a lot to do with that music that's in that culture, too. Just the way that some of that music is so vulgar and like, bitch, pimp, and that, you know.
Kara Connolly
Yeah. Stuff's glorified.
Theo
Yeah, that's a good point. I think that that culture has the most glorification of the music of the performers. Now, a lot of the. A lot of the producers and agents of that group are white, so certainly just as much.
Kara Connolly
Yeah. They're involved, too.
Theo
Responsibility. Yeah. Thank you so much for hanging out. I want to know, what do you like to do now? So are you retired now?
Kara Connolly
I just retired three months ago.
Theo
Congratulations.
Kara Connolly
Thank you so much. Very happy. I put in. You're supposed to put in 32 years to get your full pension, but I gave up after 31.
Theo
What?
Kara Connolly
Yeah, 32 years.
Theo
You get your. So you still get. You still get a pension?
Kara Connolly
No, I get my pension. It's just not. The most you're going to get is 8, 80% of your salary after 32 years. And I stayed till 31 years and I get like 77% or something.
Theo
That's fair.
Kara Connolly
Yeah. I'm down south now. I go to the beach. I paint. I do oil painting as a hobby.
Theo
You do? Yeah. Would you do us a little bitty painting and we could put it in?
Kara Connolly
No, I'm terrible. I'm just learning. I copy artists that I like. That's how I'm learning. It's like mixed colors and stuff like that. So I copy artists, paintings, things that I appreciate, and I try to recreate them just in the learning process. I'm terrible. I'm brand new.
Theo
If you ever do want to do something even small and it can even be years from now, you want to.
Kara Connolly
I'll send you a little painting.
Theo
Yeah.
Kara Connolly
My niece is an actual painter, and I told her I was coming. She's like, bring. Bring Theo a painting.
Theo
Oh, that's cool. That's sweeter. Well, I'm glad that I asked. That would be really nice to Have. Because then I can tell people who it's from. All right. And thank you so much for your service.
Kara Connolly
Thank you so much. Thank you for having me. Thank you for having normal people on and not just. Just, you know, like you. It's nice to have someone who gives a shit what we're doing instead of, you know.
Theo
Yeah. Well, I think I'm learning more that. That's just so much more important to me. Sometimes I think. I don't know, this whole thing has been interesting, like, just talking to people and stuff like that, because I'm not really the best interviewer, but I do. I am curious about people.
Kara Connolly
Well, that's what makes a good interview. You ask people questions. You know, You're a great interviewer. Come on.
Theo
Wow, that's sweet of you. Thank you.
Kara Connolly
You're welcome. I love the Amish kid interview. That was great.
Theo
Oh, he was good.
Kara Connolly
He was great.
Theo
He was.
Kara Connolly
He was very, well, spin. He was just very direct. He seemed so natural at it. He really did.
Theo
I know.
Kara Connolly
I see your hat there. I like your.
Theo
And Louis CK Just gave me his new book. I give it to your daughter, but it's kind of for boys.
Kara Connolly
It's a boy book. Is it a novel?
Theo
It is. And he did a really great job writing.
Kara Connolly
All right. He's funny. He's funny. I know he had trouble in the past, but. He's a funny bastard.
Theo
Yeah, he is. Yeah. And I'm so glad he had trouble in the past because that's how he and I got to know each other. Each other. Because we've all had trouble and that. So it's good.
Kara Connolly
That's great.
Theo
Yeah. And in the spirit of service, we got a picture of our. This is our Jim Jeffries. He was a comedian that was on. That's his nephew, Lieutenant Max Nugent. Yeah. Who was an officer in the Australian army, and he passed away in a helicopter crash. So he is our. He's our hero. So we're excited to have him and have him there. Yeah, it's nice. Yeah, he's cool. He's got a. He seems like a neat guy, so I'm sure we'll get to know, channel some thoughts and feelings and energy from him over the years. But anyway, thank you both for your service. Congratulations on your move, and you look lovely. And I wish you a beautiful second half of your life as it evolves. Thank you for bringing your daughter. And we got you guys set up for dinner night over at 12:30 Club. That'll be fun.
Kara Connolly
That's lovely. Thank you so much.
Theo
Yeah. I appreciate you. Thank you so much.
Kara Connolly
Thank you.
Theo
Yep.
Kara Connolly
Lovely to meet you. Now I'm I'm just floating on the breeze and I feel I'm falling like these leaves I must be cornerstone.
Theo
Oh.
Kara Connolly
But when I reach that ground I'll share this peace of mind I found I can feel it in my bones but it's gonna take.
Guest: Kara Connolly
Release Date: October 9, 2025
In this episode, Theo Von sits down with retired Boston police officer and detective, Kara Connolly, who served over 30 years in the force, including a stint in the human trafficking unit. The conversation explores her career journey, gritty real-life stories from the street, the realities of police work in Boston over three decades, the impact of social changes on law enforcement, and her insights into human trafficking, detective work, and the toll of the job. The discussion is candid, at times graphic, but rich with humor and humanity.
[03:36–07:53]
[08:18–10:29]
[10:29–17:27]
"People in court ... want forensics. They want fingerprints, they want, like, cell phone records. ... CSI shows make it look like that's left at every scene." – Kara [16:41]
[20:27–21:38]
[26:19–28:49]
[29:43–44:22]
[29:43–39:02]
[44:42–52:09]
[58:59–68:01]
[71:14–94:22]
[94:21–99:48]
[101:33–113:17]
Kara expresses contentment with her retirement and gratitude for the recognition of her career. The episode closes on a warm, personal note, celebrating the resilience of those in public service, the complexity of the work, and the need to share real stories often left out of media narratives.
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This summary covers the main content and tone of Episode #616, omitting ad reads and non-content segments.