This Past Weekend w/ Theo Von – Episode #616: Retired Boston Detective

Guest: Kara Connolly
Release Date: October 9, 2025

Episode Overview

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.

Key Discussion Points & Insights

Starting Out: Early Career & Boston Policing in the ’90s

[03:36–07:53]

Kara joined the Boston Police, starting out in Dorchester and South Boston.
She explains the probationary period for new officers and the stark contrast between busy ("a ton of shootings and gang stuff" in Dorchester) and quieter districts (South Boston).
Demographics: Dorchester was more racially diverse while South Boston was “mostly white” at the time.
Misconceptions about "Southies" clarified; only outsiders pluralize it.
Early calls: Kara recounts her first "person with a gun" call – "I was shitting my pants... and it turned out to be bullshit. It wasn't even real." – Kara [06:40]
Law enforcement was riskier in the ’90s with higher crime rates—"Boston’s homicide count hit an all-time high of 152 cases" – Theo [07:53].
"It's become much safer... the gang's kind of aged out... or moved on in life." – Kara

Evolution of Police Work & Public Perception

[08:18–10:29]

Talks about the shift toward "community policing," walking beats, and changes in approach to building neighborhood relations.
Critiques modern “dancing cops” and social media outreach by police: "It's so goddamn cringy... that's not what people want when they call for help." – Kara [09:44]
Acknowledging efforts to make officers look less "paramilitary," but questions its long-term effect.

Becoming a Detective: Transition & Cases

[10:29–17:27]

Kara explains the rigorous process for detective promotion—exams, interviews, experience.
Differences between patrol and detective work. As a detective, “now you own that [case].”
Her first notable case: armed robbery of a cell phone store—“They literally tied her up with telephone cord... she hopped over to the phone all tied up with her ankles.” – Kara [13:44]
Case turned federal due to interstate commerce; suspects given long sentences because of prior records.
Importance of fingerprints in investigations and public misconceptions due to CSI-like shows.

"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]

The "CSI Effect" and Courtroom Realities

[20:27–21:38]

Kara details how TV shows have "ruined" jury expectations: "They literally come back with notes saying, why don't you have fingerprints? Why don't you have DNA?" – Kara [21:07]

Work-Life Balance, Family, and Burnout

[26:19–28:49]

Discusses the struggle of balancing detective work and family: shifts running late, holidays worked only every six years, impact on home life.
"It's tricky. It was difficult. It was a lie. It was hard." – Kara [27:21]
Transfer to the human trafficking unit partly motivated by more predictable hours.

Memorable, Graphic, and Surreal Police Calls

[29:43–44:22]

Kara recounts some of the most bizarre and harrowing calls in her career.

"Dick on the Sidewalk"

[29:43–39:02]

A mentally ill man cut off his own penis and left it on the sidewalk.
Gruesome details include following a blood trail, the body part being frozen to the pavement, and the man later returning to "kiss it" on the sidewalk.
"He leans over... tugs... threw it. ... He bent down, gave it a smooch, and got up and walked home." – Kara [36:41]

Baby in Trash Can – Miraculously Survived

[44:42–52:09]

Responding to a call about “puppies in the trash,” they discover a crying baby tied in a bag, left in a public bin by a woman who had just discreetly given birth and cleaned up after herself.
"The EMT comes walking down the street... and you can see his reaction. He picks it out, and then it's crazy activity." – Kara [46:24]
Baby is saved by a passerby who heard the crying; mother later caught and, after a long court process, received probation, not jail. Kara criticizes “cultural” defenses in court.
"I mean that's attempted murder. She tried to kill that baby. ... 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?” – Kara [51:56]

Impact of Leadership, Politics, and the Law on Policing

[58:59–68:01]

The relationship between police, the district attorney, and political leadership is crucial for effective law enforcement. "Shoplifting's no longer a crime. ... That's why shit's locked up in all these stores." – Kara [59:06]
Discusses the consequences of decriminalization of certain offenses, lack of prosecution, and the rise of smash-and-grab thefts.
Critique of former Suffolk County DA Rachel Rollins: “She was one of the ones not supportive.” – Kara [65:38]
Describes the explosion of homelessness, open-air drug use in Boston, and city decline along “Mass and Cass,” linking the crisis to these political decisions.

Human Trafficking & Sex Work Investigations

[71:14–94:22]

Kara spent 5 years in the human trafficking unit.
Most trafficking doesn't resemble movie portrayals; rarely are people “snatched off the street.”
The majority of cases were young, often vulnerable women manipulated and groomed by pimps.
"It's always kind of something missing — could just be they weren't getting attention at home or they weren't happy. And the pimps... very charming." – Kara [72:06]
Asian-run spas worked differently, moving women frequently to avoid detection and exploiting language barriers.

"John Stings": Undercover Operations

Kara and her team targeted sex buyers via online ads, meeting men in hotels to make arrests.
"Every time we did it, we got a doctor. Every fucking time." – Kara [80:21]
Unique terminology in the sex trade explained: gfe (girlfriend experience), Russian, Greek, bareback (bbb).
“Northeastern University professor... will you put me in yoga positions? That’s what he wanted.” – Kara [81:35]

Observations on Buyers and Sellers

Most buyers were married, sometimes fainting upon arrest; some were affluent, others working class.
"I hated telling people I worked there because it was like a conversation killer. ... Well, it’s just interesting how perverse, like, sexuality can get." – Kara [90:56]

The Complexities of Helping Victims

Many women returned to pimps or refused to testify; sustainable change was rare.
“You can't help people till they are ready for some help.” – Theo [93:38]

High-Stakes, Long-Term Investigations

[94:21–99:48]

Kara recounts a successful three-year joint investigation with Homeland Security that brought down a violent, prolific trafficking ring operating across multiple states.
"Took like three years to get enough people to... testify… I think he got like 33 years in jail." – Kara [97:36]
She was awarded “Detective of the Year” and recognized by Mark Wahlberg and Peter Berg at the ceremony.

Human Side of Policing & Retirement

[101:33–113:17]

After moving from Boston to Charleston, South Carolina, Kara reflects on life after retirement and the importance of having friends "outside the job"—something not always easy as police culture is insular and can feel isolating.
"You don't want to feel like you're on all the time. ... We are not fit for public society." – Kara [103:08]
She spends her time painting, enjoying the beach, and spending time with her daughter.

Notable Quotes & Deep Dives

“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?” – Kara [21:07]
“I was going to write a book... ‘Dick on the Sidewalk and Other Stories from the Street’.” – Kara [29:43]
“Some people are just bad people. Some people end up that way because of the way they’re raised. And some people are just bad.” – Kara [110:42]
“Dick on the sidewalk sounds funny. But that was a suck morning. ... More for that kid than me. ... Baby in a trash can and all this other. It’s hard.” – Kara [102:24]
“Human trafficking is like when someone’s trafficked ... to sell sex ... through coercion or force or threats...” – Kara [72:06]
“You can’t help people till they are ready for some help.” – Theo [93:38]
Theo on changes in policing: "I wonder if it's what we are doing or what is being done to us that's having more of an effect..."

Timestamps for Important Segments

03:36 — Kara Connolly’s background and early years as a Boston cop
07:53 — Boston crime rates in the ’90s; the realities of gang violence
13:44 — Detailed armed robbery case
16:41 — The importance of (and misconceptions about) forensic evidence
21:07 — How TV and juries have made prosecution harder
29:43 — "Dick on the Sidewalk": Gruesome, surreal police call
44:42 — Baby left in trash can, miraculous rescue story
59:06 — DA’s policies and the explosion in property crimes and theft
65:38 — Impact of “decriminalization,” city decline, and Mass & Cass
71:14 — Defining human trafficking and realities behind the crime in Boston
80:21 — Doctors and professionals caught in sex stings
94:21 — Three-year investigation, federal charges, winning “Detective of the Year”
101:33 — Life after the force; transition to Charleston and reflections on friendships

Tone & Atmosphere

Conversational and real—plenty of humor mixed with the dark and graphic truths of being a cop.
Kara’s storytelling is vivid, forthright, and often self-deprecating.
Theo balances curiosity, levity, and respect for tough subject matter.

Closing & Reflections

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.

For More:
Follow Theo Von and "This Past Weekend" on your favorite podcast platform.

This summary covers the main content and tone of Episode #616, omitting ad reads and non-content segments.

This Past Weekend w/ Theo Von – Episode #616: Retired Boston Detective

Guest: Kara Connolly
Release Date: October 9, 2025

Episode Overview

Key Discussion Points & Insights

Starting Out: Early Career & Boston Policing in the ’90s

[03:36–07:53]

Kara joined the Boston Police, starting out in Dorchester and South Boston.
She explains the probationary period for new officers and the stark contrast between busy ("a ton of shootings and gang stuff" in Dorchester) and quieter districts (South Boston).
Demographics: Dorchester was more racially diverse while South Boston was “mostly white” at the time.
Misconceptions about "Southies" clarified; only outsiders pluralize it.
Early calls: Kara recounts her first "person with a gun" call – "I was shitting my pants... and it turned out to be bullshit. It wasn't even real." – Kara [06:40]
Law enforcement was riskier in the ’90s with higher crime rates—"Boston’s homicide count hit an all-time high of 152 cases" – Theo [07:53].
"It's become much safer... the gang's kind of aged out... or moved on in life." – Kara

Evolution of Police Work & Public Perception

[08:18–10:29]

Talks about the shift toward "community policing," walking beats, and changes in approach to building neighborhood relations.
Critiques modern “dancing cops” and social media outreach by police: "It's so goddamn cringy... that's not what people want when they call for help." – Kara [09:44]
Acknowledging efforts to make officers look less "paramilitary," but questions its long-term effect.

Becoming a Detective: Transition & Cases

[10:29–17:27]

Kara explains the rigorous process for detective promotion—exams, interviews, experience.
Differences between patrol and detective work. As a detective, “now you own that [case].”
Her first notable case: armed robbery of a cell phone store—“They literally tied her up with telephone cord... she hopped over to the phone all tied up with her ankles.” – Kara [13:44]
Case turned federal due to interstate commerce; suspects given long sentences because of prior records.
Importance of fingerprints in investigations and public misconceptions due to CSI-like shows.

"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]

The "CSI Effect" and Courtroom Realities

[20:27–21:38]

Kara details how TV shows have "ruined" jury expectations: "They literally come back with notes saying, why don't you have fingerprints? Why don't you have DNA?" – Kara [21:07]

Work-Life Balance, Family, and Burnout

[26:19–28:49]

Discusses the struggle of balancing detective work and family: shifts running late, holidays worked only every six years, impact on home life.
"It's tricky. It was difficult. It was a lie. It was hard." – Kara [27:21]
Transfer to the human trafficking unit partly motivated by more predictable hours.

Memorable, Graphic, and Surreal Police Calls

[29:43–44:22]

Kara recounts some of the most bizarre and harrowing calls in her career.

"Dick on the Sidewalk"

[29:43–39:02]

A mentally ill man cut off his own penis and left it on the sidewalk.
Gruesome details include following a blood trail, the body part being frozen to the pavement, and the man later returning to "kiss it" on the sidewalk.
"He leans over... tugs... threw it. ... He bent down, gave it a smooch, and got up and walked home." – Kara [36:41]

Baby in Trash Can – Miraculously Survived

[44:42–52:09]

Responding to a call about “puppies in the trash,” they discover a crying baby tied in a bag, left in a public bin by a woman who had just discreetly given birth and cleaned up after herself.
"The EMT comes walking down the street... and you can see his reaction. He picks it out, and then it's crazy activity." – Kara [46:24]
Baby is saved by a passerby who heard the crying; mother later caught and, after a long court process, received probation, not jail. Kara criticizes “cultural” defenses in court.
"I mean that's attempted murder. She tried to kill that baby. ... 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?” – Kara [51:56]

Impact of Leadership, Politics, and the Law on Policing

[58:59–68:01]

The relationship between police, the district attorney, and political leadership is crucial for effective law enforcement. "Shoplifting's no longer a crime. ... That's why shit's locked up in all these stores." – Kara [59:06]
Discusses the consequences of decriminalization of certain offenses, lack of prosecution, and the rise of smash-and-grab thefts.
Critique of former Suffolk County DA Rachel Rollins: “She was one of the ones not supportive.” – Kara [65:38]
Describes the explosion of homelessness, open-air drug use in Boston, and city decline along “Mass and Cass,” linking the crisis to these political decisions.

Human Trafficking & Sex Work Investigations

[71:14–94:22]

Kara spent 5 years in the human trafficking unit.
Most trafficking doesn't resemble movie portrayals; rarely are people “snatched off the street.”
The majority of cases were young, often vulnerable women manipulated and groomed by pimps.
"It's always kind of something missing — could just be they weren't getting attention at home or they weren't happy. And the pimps... very charming." – Kara [72:06]
Asian-run spas worked differently, moving women frequently to avoid detection and exploiting language barriers.

"John Stings": Undercover Operations

Kara and her team targeted sex buyers via online ads, meeting men in hotels to make arrests.
"Every time we did it, we got a doctor. Every fucking time." – Kara [80:21]
Unique terminology in the sex trade explained: gfe (girlfriend experience), Russian, Greek, bareback (bbb).
“Northeastern University professor... will you put me in yoga positions? That’s what he wanted.” – Kara [81:35]

Observations on Buyers and Sellers

Most buyers were married, sometimes fainting upon arrest; some were affluent, others working class.
"I hated telling people I worked there because it was like a conversation killer. ... Well, it’s just interesting how perverse, like, sexuality can get." – Kara [90:56]

The Complexities of Helping Victims

Many women returned to pimps or refused to testify; sustainable change was rare.
“You can't help people till they are ready for some help.” – Theo [93:38]

High-Stakes, Long-Term Investigations

[94:21–99:48]

Kara recounts a successful three-year joint investigation with Homeland Security that brought down a violent, prolific trafficking ring operating across multiple states.
"Took like three years to get enough people to... testify… I think he got like 33 years in jail." – Kara [97:36]
She was awarded “Detective of the Year” and recognized by Mark Wahlberg and Peter Berg at the ceremony.

Human Side of Policing & Retirement

[101:33–113:17]

After moving from Boston to Charleston, South Carolina, Kara reflects on life after retirement and the importance of having friends "outside the job"—something not always easy as police culture is insular and can feel isolating.
"You don't want to feel like you're on all the time. ... We are not fit for public society." – Kara [103:08]
She spends her time painting, enjoying the beach, and spending time with her daughter.

Notable Quotes & Deep Dives

“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?” – Kara [21:07]
“I was going to write a book... ‘Dick on the Sidewalk and Other Stories from the Street’.” – Kara [29:43]
“Some people are just bad people. Some people end up that way because of the way they’re raised. And some people are just bad.” – Kara [110:42]
“Dick on the sidewalk sounds funny. But that was a suck morning. ... More for that kid than me. ... Baby in a trash can and all this other. It’s hard.” – Kara [102:24]
“Human trafficking is like when someone’s trafficked ... to sell sex ... through coercion or force or threats...” – Kara [72:06]
“You can’t help people till they are ready for some help.” – Theo [93:38]
Theo on changes in policing: "I wonder if it's what we are doing or what is being done to us that's having more of an effect..."

Timestamps for Important Segments

03:36 — Kara Connolly’s background and early years as a Boston cop
07:53 — Boston crime rates in the ’90s; the realities of gang violence
13:44 — Detailed armed robbery case
16:41 — The importance of (and misconceptions about) forensic evidence
21:07 — How TV and juries have made prosecution harder
29:43 — "Dick on the Sidewalk": Gruesome, surreal police call
44:42 — Baby left in trash can, miraculous rescue story
59:06 — DA’s policies and the explosion in property crimes and theft
65:38 — Impact of “decriminalization,” city decline, and Mass & Cass
71:14 — Defining human trafficking and realities behind the crime in Boston
80:21 — Doctors and professionals caught in sex stings
94:21 — Three-year investigation, federal charges, winning “Detective of the Year”
101:33 — Life after the force; transition to Charleston and reflections on friendships

Tone & Atmosphere

Conversational and real—plenty of humor mixed with the dark and graphic truths of being a cop.
Kara’s storytelling is vivid, forthright, and often self-deprecating.
Theo balances curiosity, levity, and respect for tough subject matter.

Closing & Reflections

For More:
Follow Theo Von and "This Past Weekend" on your favorite podcast platform.

This summary covers the main content and tone of Episode #616, omitting ad reads and non-content segments.

#616 - Retired Boston Detective

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Summary

This Past Weekend w/ Theo Von – Episode #616: Retired Boston Detective

Episode Overview

Key Discussion Points & Insights

Starting Out: Early Career & Boston Policing in the ’90s

Evolution of Police Work & Public Perception

Becoming a Detective: Transition & Cases

The "CSI Effect" and Courtroom Realities

Work-Life Balance, Family, and Burnout

Memorable, Graphic, and Surreal Police Calls

"Dick on the Sidewalk"

Baby in Trash Can – Miraculously Survived

Impact of Leadership, Politics, and the Law on Policing

Human Trafficking & Sex Work Investigations

"John Stings": Undercover Operations

Observations on Buyers and Sellers

The Complexities of Helping Victims

High-Stakes, Long-Term Investigations

Human Side of Policing & Retirement

Notable Quotes & Deep Dives

Timestamps for Important Segments

Tone & Atmosphere

Closing & Reflections

Summary

This Past Weekend w/ Theo Von – Episode #616: Retired Boston Detective

Episode Overview

Key Discussion Points & Insights

Starting Out: Early Career & Boston Policing in the ’90s

Evolution of Police Work & Public Perception

Becoming a Detective: Transition & Cases

The "CSI Effect" and Courtroom Realities

Work-Life Balance, Family, and Burnout

Memorable, Graphic, and Surreal Police Calls

"Dick on the Sidewalk"

Baby in Trash Can – Miraculously Survived

Impact of Leadership, Politics, and the Law on Policing

Human Trafficking & Sex Work Investigations

"John Stings": Undercover Operations

Observations on Buyers and Sellers

The Complexities of Helping Victims

High-Stakes, Long-Term Investigations

Human Side of Policing & Retirement

Notable Quotes & Deep Dives

Timestamps for Important Segments

Tone & Atmosphere

Closing & Reflections