They Bet on Black: The Story of the Gambling Nuns w/ Deanna Ortiz

Summary

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Podcast Summary: The Nightly

Episode: They Bet on Black: The Story of the Gambling Nuns w/ Deanna Ortiz

Host: Hatch Podcasts (KP)
Guest: Deanna Ortiz (Comedian, Host of "Crime for Bed")
Date: December 26, 2025

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Episode Overview

This cozy Nightly episode features a hilarious and surprisingly wild deep-dive with Deanna Ortiz into the true story of Sister Mary Margaret Cooper and Sister Lana, two Catholic nuns who ran a 20-year embezzlement scheme to fuel their secret gambling trips to Las Vegas. With signature bedtime banter and pop culture references, KP and Deanna unpack the whole “holy heist,” reminisce on school fundraising oddities, and debate just how cold-hearted (or hapless) these nuns actually were.

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Key Discussion Points & Timeline

1. Tea, Sleepwear, and Wholesome Crimes

[00:29 – 02:05]

• KP and Deanna kick things off with cozy evening rituals: tea, sleep caps, and the joys (and hazards) of pretend arson.
• Lead-in to tonight’s true crime tale: Deanna is famous for her "Crime for Bed" stories—quirky, real-life crime stories that won’t keep you up at night.

"The only crime we commit is stealing a few Z's." – KP [00:29]

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2. Set Up: Enter Sister Mary Margaret, High Roller

[02:06 – 05:24]

• Deanna introduces Sister Mary Margaret Cooper, a long-serving nun/principal at St. James Catholic School in Torrance, California.
• She was strict, old-school, and the sort of nun "who’d pick making you walk the playground perimeter over detention." [04:00]
• The school was always on a tight budget, leading to a quirky annual casino night fundraiser—"because nothing says Catholic school like blackjack for the kids’ roof fund." [05:24]

“When I’m picturing her, I picture the stereotypical nun. The clothes, not a hair out of place. She’s very strict. And actually, a lot of the students that she taught have the same memory… her favorite punishment being walking the perimeter of the playground.” – Deanna [04:04]

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3. The Nuns’ Vegas Double Life

[05:24 – 08:44]

• Sister Mary Margaret and her close associate, Sister Lana, ran the casino fundraiser—and always “won big.” Parents noticed but “what are they gonna do, accuse a nun of stealing?”
• The two began taking regular trips to Vegas, even renting a townhouse every summer to gamble through the night—a “bachelorette party for two nuns among the Vegas chaos.”
• Their “mysterious rich uncle” cover story turned eyes away from their increasingly lavish behavior.

“Anytime that they did this fundraiser, the people who would always win big was Sister Mary and Sister Lana. No, Sister—surprise! They would walk away with the big prizes of the night… but what are they gonna do, accuse a nun of stealing?” – Deanna [05:53 – 06:13]

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4. The Long Con Unravels

[08:44 – 12:45]

• Sister Mary Margaret, handling all school finances, was able to embezzle funds undetected for years.
• The scheme is uncovered when the church decides to audit the books upon Sister Mary’s retirement in 2018. Suddenly, “red flags everywhere.”
• A family notices their tuition check is cashed into the wrong account; as the investigation snowballs, the scale of theft is revealed—over $800,000 gone over 20 years.
• The money was meant for vital repairs and children’s needs, instead funneled to “the roulette table.”

“The only reason that she was able to get away with it is because she was the one making the calls. She was the accountant, she was the finance. She did everything.” – Deanna [09:17]

“When they added all of the stolen money up, it was over $800,000 that went into the sisters’ pockets.” – Deanna [10:05]

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5. Reactions and Consequences

[12:05 – 13:50]

• The school’s response: quietly fire the nuns without calling police. “The optics are not good on that. You do not want to be the one that's doing that” (accusing a nun of theft). – KP [06:13]
• Parents are outraged and rally to press charges. The story goes public; both nuns are arrested for embezzlement.
• At 80 years old, Sister Mary Margaret is sentenced to 366 days in federal prison and ordered to pay back $825,000.

“If I went to jail and my bunky was a nun—like an old stealing nun—that’s a little hardcore, right?” – Deanna [13:39]

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6. The Reflection: Motives, Morality, and Movie Pitches

[13:50 – 15:48]

• Deanna and KP debate whether the sisters were calculated criminals or just in over their heads—concluding perhaps Sister Mary Margaret was colder, and Sister Lana a bit swept up.
• Pop culture segues: the guests dream up an HBO adaptation (“Ocean’s 15”), and draw parallels to Thelma and Louise or “two best friends running against the grain.”

“I want a movie. I want an Ocean’s 15…very Thelma & Louise to me. Two best friend women running against the grain. It’s fun.” – KP [14:29]

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7. “Would You Rather” Game: Crime Drama Edition

[16:09 – 17:53]

• In the spirit of late-night unwinding, KP and Deanna play a “Would You Rather” game with comedic takes:
  • Be the first interviewed, “gruff witness” in a Law & Order episode
  • OR the murder victim in a British seaside crime drama

“It’s always by the sea…and you get justice. Usually those British crime solvers, they’ll get you.” – KP [17:07]

• Both riff about their dream minor character roles and the joys of clichéd TV crime tropes.

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8. Closing Notes

[17:59 – 18:16]

• KP thanks Deanna for the “absolute trip” of a story; the episode winds down with light-hearted reflections on nuns, Vegas, and the surreal charm of bedtime crime stories.

“What an absolute trip. I love it, and I hope I dream of them tonight. Lana and Sister Mary Margaret, thank you so much for sharing your crime story with us.” – KP [17:59]

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Notable Quotes & Memorable Moments

• On the strange optics of the scam:
  “But what are they gonna do, accuse a nun of stealing?” – Deanna [06:13]

• On the unorthodox fundraiser:
  “...I can see why it really popped off, because I would imagine the parishioners are like, looking to be able to do a little sin. And then it’s like, if it’s hosted by the church, you don’t feel bad.” – KP [05:24]

• On Vegas nun life:
  “Two nuns, a bachelorette party, and, like, I don't know, Lady Gaga all at the poker table.” – Deanna [06:52]

• On intentions and morality:
  “I think Sister Mary is cold hearted. And I think Lana more got wrapped up in it and was like, everything—no problem, we'll figure it out.” – Deanna [15:12]

• On prison bunkmates:
  “If I went to jail and my bunky was a nun—like an old stealing nun—that’s a little hardcore, right?” – Deanna [13:39]

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Highlights & Takeaways

• Almost cinematic in its absurdity, the story combines unlikely criminal masterminds (nuns!) with classic themes of temptation, trust, and the pitfalls of putting too much financial control in one person’s hands.
• The hosts keep the tone cozy and humorous, ensuring the story feels like a wild bedtime tale rather than true crime horror.
• Lively pop culture tangents and a playful ending “Would You Rather” segment provide a soothing wind-down.

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Essential Timestamps

• [02:12] – Story of Sister Mary Margaret begins
• [05:24] – The Catholic School “casino night” fundraiser
• [06:52] – Nuns’ double life in Las Vegas
• [08:44] – The discovery and unraveling of the embezzlement
• [10:05] – The $800,000 revelation
• [12:45] – Consequences: legal action, prison, and repayment
• [14:29] – Movie/TV pitches and the moral debate
• [16:21] – “Would You Rather” game segment

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For late-night listeners or fans of light true crime with a twist, this episode delivers a hilarious, bizarre, and memorable tale of two nuns who truly bet big.

Transcript

[A]

Hello. You're about to drift into an episode of the Nightly a podcast designed to help you unwind and relax. For the full phone free immersive light experience. Visit Hatch Co. Enjoy.

[B]

Hi there everyone and good evening. I am kp. Welcome to the Nightly on Hatch, where the only crime we commit is stealing a few Z's. Speaking of crime tonight, we are joined again by Deanna Ortiz. She is a fabulous comedian and host of the Hatch Bedtime podcast. You know it. You love it. Crime for bed. Hi, Deanna.

[C]

Hi. How are you?

[B]

I'm good, thank you. How's it going with your. With your cozy little evening this evening?

[C]

Oh, it's going good. Yeah. I'm just, you know, got a tea warmed up, ready to dive into some crimes.

[B]

Ooh, man, I kind of got to get into tea. I do a morning tea, but I got to do evening teas.

[C]

A cozy time tea. It's like, especially now that it's getting colder outside and it's like it is just the perfect little final end to the night.

[B]

Yeah. I mean, they kind of sell me alone with just a sleepy bear in a nighttime cap. That is enough for me to want to get on in.

[C]

Should we all get into like caps and sleeping gowns now?

[B]

I wonder about the cap because that's gonna fall right off. But I guess a bonnet would be better. I know that's good for your hair.

[C]

Yeah.

[B]

But it does need the long trail.

[C]

That's part of the allure. Yeah. The longness and a stub of candle as I putter around my house.

[B]

That I would really like to do, but I would trip and light my house aflame. Speaking of crimes like arson.

[C]

Yeah.

[B]

I think you have another amazing crime for bed story to share with us over here, don't you?

[C]

I do, yeah. So this story is a little crazy and I just first have to ask, do you gamble? Do you gamble at all? Do you go to the casino?

[B]

I have. I'm not opposed to it. Like if someone suggests it, I'll get on in there. Yeah.

[C]

It's the craziest thing about me. Every time I go to the casino, I hit it big. I win, I go in for five minutes, I make $400 and I walk out.

[B]

Oh my gosh. Wow. That is very, very cool. That's a great little like life hack to have.

[C]

Yeah, but. And it's only for slots and I. I don't know how to count cards. But if there was a place that I'm gonna cheat at, it is gonna be poker. And that's what Brings us into our story that I have today is the story about the gambling nun, Sister Mary Margaret Cooper.

[B]

I am so in with just the title. Wow.

[C]

So Sister Mary Margaret, great name. While she was entrusted with watching over the children of Southern California Catholic School that she was working at, she also kept a watchful eye over their tuition checks. Year after year, she filled her pockets with the school's money and headed straight to Vegas. And I'm not so sure about, like, the tenets of the Bible, but, like, thou shalt not steal is definitely one of them. But I do think maybe we should add.

[B]

Yeah, steal is up there.

[C]

Is there anything about betting on black?

[B]

See, there's nothing on that. And then they technically didn't use the word embezzle. And that's a separate form.

[C]

So you can get.

[B]

You can really pull hairs on some of that.

[C]

We get into semantics on this. I love it. So a little bit of background on Sister Mary Margaret. She started working at a Catholic school in Torrance, California, in 1988. She had kind of working all over California with. At different schools before settling down in the Torrance area, where she stayed at the school, St. James Catholic School, for 30 years. It was a small school. It had, like, 300 students. And she was basically the principal. There was no principal title, but that's basically what she was doing. And when I'm picturing her, I picture the stereotypical nun. You know, the clothes, not a hair out of place. She's very strict. And actually, a lot of the students that she taught have the same memory of just, like, her favorite punishment being walking the perimeter of the playground as a punishment instead of, I don't know, detention.

[B]

Huh. Okay. Getting the steps in.

[C]

Yeah. A classic nun.

[B]

She's also quite classic. Cause it really doesn't get more classic than Mary Margaret. Sister Mary Margaret is kind of the name you use when you're like, oh, what should I name this nun character? It's like, yeah, go with the classic, right?

[C]

Yes. An old favorite. The entire time she's at this school, they're, like, running on a small budget. So the school has fundraisers constantly to raise more money. And the number one, like, biggest successful fundraiser that they had was when they turned the school into a makeshift casino, which I think is so crazy for a Catholic school to, like, play poker for a fundraiser. Like, just have a bake sale like everybody else.

[B]

But I guess they're trying to, like. I can see why it's really popped off, because I would imagine the parishioners are, like, looking to be able to do a little sin. And then it's like, if it's hosted by the church, you don't feel bad. Like, you can. You can feel good going to the church's casino. Maybe you'd feel a little worse going to another casino.

[C]

Right? And you're like, oh, it's all for the kids, but I do get to play blackjack.

[B]

Yeah. They're, like, putting their whole house down payment on this one event for the school.

[C]

So anytime that they did this fundraiser, the people who would always win big was Sister Mary and Sister Lana. No, Sister Surprise. They would walk away with the big prizes of the night. If it was, like, a raffle prize or, like, you know, some donations, they were the two taking it home. But the parents didn't really, like, raise an eye. I mean, what are they gonna do, accuse a nun of stealing?

[B]

Like, the optics are not good on that. You do not want to be the one that's doing that.

[C]

What a lucky nun. I guess that's what we're gonna, you know, chalk it up to that. So Sister Lana was the other nun in Kahoot with Sister Mary. She was hired in 96. And they were basically, like, besties. They would make regularly scheduled trips to Vegas, and they were roommates at one point. And on their summer breaks, they would just, like, rent a townhouse in Vegas and just, like, sit at the poker table until, like, early in the morning. And I would love to see that. Two nuns, a bachelorette party, and, like, I don't know, Lady Gaga all at the poker table.

[B]

That's incredible. And, you know, they were a hit. That's the thing is, like, Vegas is, like, desperate for, you know, anyone that's got something different going on. And, you know, walking in with your habits on. These two would be a total hit. They're getting bought. I guess they probably don't drink, but I don't know. Their moral compass is a little different than I've known. So maybe they do drink, but they're getting bought something.

[C]

I feel like at this point, if, like, you are a gambling nun, like, have a glass of red wine. Sure, sure.

[B]

That's true. Yeah, Have a little of Jesus's blood.

[C]

There we go. Come on.

[B]

Throw him back at the table.

[C]

And so anytime that anyone would, like, even question what the sisters were doing, they would say, oh, well, Sister Lana has a mysterious, rich uncle who's giving her all this money, and I have covered a million crimes. Everyone always has a mysterious, rich uncle, without fail.

[B]

Everyone but me. I would love one. Okay, interesting.

[C]

So this goes on for 20 years, the sisters have a second house in Vegas. They're considered high rollers at their favorite casino. 20 years of gambling. And then in 2018, Sister Mary is ready to retire. So this was the catalyst for like finding it everything out to get ready for her retirement. The church decides to do an audit to get the church's finances in order while they find a replacement. So it all was never retire. I guess that's the moral.

[B]

What I. Yeah, I assume nuns, when they retire are basically just still doing nun stuff.

[C]

Right? What do you.

[B]

I guess, I don't know. I guess she just doesn't have to make kids walk the perimeter anymore.

[C]

Even thought about that, like, what would she even do? Where would she even go?

[B]

She's probably still just going to spend like a lot of time chilling, praying and baking.

[C]

I don't know.

[B]

Maybe. Maybe my non knowledge is limited.

[C]

I will say very limited. Going to Vegas. Maybe she'll retire in Vegas.

[B]

Yes.

[C]

So once she gets word of the audit, Sister Mary starts kind of losing her mind. She starts asking for different files to be moved. She starts moving some funds around in different accounts, but it was already too far gone. The auditor had already started looking through the school's history. And while they started this basic bookkeeping process, they quickly found out that things weren't adding up. The sister's long con of cashing the student's tuition checked into their own personal account and siphoning off fundraiser money into their own pocket for 20 years was quickly found out. And the only reason that she was able to get away with it is because she was the one making the calls. She was the accountant, she was the finance. She did everything.

[B]

Of course, like, a lot of people wouldn't want to accuse a nun of anything, but auditors, they're going to do that. Auditors don't care. They get. They're salivating at the idea that they can catch somebody. Oh yeah, I think an auditor is happy to get the nun. Be like, no, it was her. And get her the second and that's thing.

[C]

It's like they did this for 20 years and almost immediately they were like, whoa, whoa, like red flags everywhere.

[B]

Totally.

[C]

Around this same time, a family started like looking into some issues with their tuition check. And they saw that the tuition check that they wrote for their kids was getting cashed into a different account. And so everything started adding up and kind of like a snowball. And towards the end of it, when they added all of the stolen money up, it was over $800,000 that went into the sister's pockets.

[B]

That is so much. That is like, I knew it was going to be a lot, but I guess to me I was like, how much money could there possibly be in a church in general?

[C]

Yeah.

[B]

Because it was like, you know, you don't expect. I guess it's over 20 years, but oh my gosh, $800,000 she went to Vegas with.

[C]

Yeah.

[B]

Did she win big, you said? Yeah, sometimes she would win. Right. Where is she holding her own money? Just in her own, like under her mattress.

[A]

Right.

[C]

I think this is the, this is where like the speculation comes in. I think that she was just a really, really addicted to gambling. And so that any time that she would get in over her head, she would take a little bit from the fund and put it into her own account and then a little bit more.

[B]

I see. Yeah, right.

[C]

I think that's what it is of like she has her own bank account that she' just like, oh, I'll just take a little bit and I'll replace it. That's the thing. People justify it in their head by saying like, oh, I'll put it back before anybody realizes that it's gone. And then slowly it's $800,000.

[B]

That's a lot of money. And then Lana was in on some of this too. So she was, she's going down for this too.

[C]

Oh, yeah. Yes. So and the other thing is that like this was all the money that was used for the fundraisers. Like they needed a new roof for the school, the kids needed, you know, all this other stuff. And it was just being siphoned off into, I don't know, the roulette table.

[B]

That is tough. I can't believe that there wasn't a point when she, I mean, her whole day is spent confessions and repenting. I believe there was just no dissonance.

[C]

Right. I have two ways of thinking of this right now where I'm like, oh, maybe they just were in over their head and they couldn't see the forest for the trees. Or maybe they were just like cold hearted nuns that stole from children. Maybe there could be two ways, you know?

[B]

Okay, wow.

[C]

After all this realization, the school calls a meeting with the parents and they tell them, hey, Sister Lana and Sister Mary are no longer working with us. They spoke on behalf of the two women saying that they take responsibility, they're really sorry, and they are no longer working at the school. But because it's a private school, the church decided to not bring the police into it. The sisters basically went off the grid and the Parents lost their minds. They like, totally were completely, you know, incensed. And they rallied together to bring the consequences down. And eventually the two sisters are taken into custody for embezzlement. Once in custody, Sister Mary admits to stealing the money from the church. And she's 80 years old at this point.

[B]

Oh, my gosh. Well, she's retired, right? Yeah, she got her retirement. She's gonna be sitting around for a bit.

[C]

She took her retirement? Yeah. At 366 days in federal prison.

[B]

A whole year. Okay.

[C]

A whole year. Yeah.

[B]

Yeah. My goodness.

[C]

It's good.

[B]

It's good. I understand why the priest was like, I can't really be like again. There's optics here, I imagine, where the, the head of the school can't be like, and we're gonna get her dragged out of here by the cops. But I get that the parents are like, no, no, we are. We will do that. Yeah.

[C]

Oh, oh, no problem. But actually, we can.

[B]

No worries.

[C]

Right?

[B]

Stand aside.

[C]

We'll just give them a couple Hail Marys and just know that they feel really bad.

[B]

Yeah, we're gonna go ahead and do that.

[C]

They also had to pay back $825,000 back to the family and, like, that's the end of it. This 80 year old nun went to jail. And I know that crimes are bad. I know crimes are bad. But if I went to jail and my bunky was a nun, like an old stealing nun. That's a little hardcore, right?

[B]

I have to imagine she did kind of well in there. Maybe I'm overemphasizing how rare and cool it is to see nuns, but I am like, I bet in prison you got a nun and she's good at gambling. Yeah, we're playing. We're playing dice or something.

[C]

Exactly. Exactly. Yes.

[B]

Dare I say maybe her retirement was kind of fun. Wow. And Lana went too. I don't know why I'm so stuck on Lana, but I'm like, it is wild that those two just had this cool little, like, best friendship.

[C]

Yeah, yeah. She went to that. Like, the Sister Mary was already stealing. And then Sister Lana comes in and she's like, girl, you're gonna love this place. Let's, let's. How good are you at Pokemon?

[B]

I got you, sweetheart.

[C]

Exactly. Yeah.

[B]

Lana's like, I'm in, fully. Wow. I want a movie. I want an Ocean's 15. I want a HBO show. I don't know what I want, but I need it. I want to see this come to life because it's very Thelma Louise to me. Very like, you know, two best friend women running against the grain. It's fun.

[C]

I love the idea of a double life, too. Like the two in Vegas, maybe they like, really, you know, they let their hair down and they. They gamble, they party. They're out with the Backstreet Boys at the Sphere Arena.

[B]

Yeah. Now, you said you're of two minds. One is they're cold hearted. The other is like they just got wrapped up. What do you think more of if you had to choose?

[C]

I think Sister Mary is cold hearted. And I think Lana more got wrapped up in it and was like, everything.

[B]

We'll work it out.

[C]

No problem. We'll figure it out. Yeah, yeah.

[B]

Cause I would have to imag. If she was 80 when she got caught. She was like 60 when she started this whole kind of scheme. True.

[C]

Yeah, yeah, yeah, yeah.

[B]

Because you said it'd been going for like 20 years, so I have to imagine her intentions were at one point very pure. You joined the nunnery early on, so I have to imagine at some point her intentions were pure. And then perhaps the kids. I'm gonna say the kids drove her to it. I'm gonna blame them.

[C]

Good. Yeah, me too. Yeah. These kids.

[B]

I actually think it's those nasty little kids.

[C]

Yeah.

[B]

Well, Deanna, that was such an absolute ride. Thank you for sharing. Should we end it off with a little thrills? Just like these nuns like to catch by playing a game?

[C]

Yes. Let's do it. Okay.

[B]

Let's play a little. Would you rather. This is not a gambling game. I think we can't get addicted.

[C]

Okay.

[B]

Okay. Would you rather play the first interviewed witness in a Law and Order episode? Like, you know, that very Brooklyn guy moving crates at the dock? That guy. That kind of vibe. Or play the murder victim in a small town British crime drama?

[C]

Oof. I think I'm gonna have to go. Murder victim. Small town British crime drama. Because the twists and turn are always so good and the small town vibes. And it's like, you know, by the sea and it's cold.

[B]

It's always by the sea.

[C]

Yeah. Yeah. That brings me back to my tea. I mean, I'm dead in it, but. But that would be. That would be very fun.

[B]

It's always on a rocky cliff on a gray day. And you get justice. Usually those. Those British crime solvers, they'll get you.

[C]

Yeah.

[B]

I'm gonna choose. I do love the witnesses in Law and Order because they are just. I've never seen people be so rude to cops in real life, but I love the New York sensibility of the law and order where anytime these two lovely cops come to them, the people are like, what's it worth to you? And just really giving them, ribbing them out. I like that.

[C]

Yeah, I saw the guy.

[B]

I don't know. They, like, want to get greased up like it's 1940s. I love. I love that.

[C]

I love it. And then a lot of times that first person comes in again, so it's like, you could. Maybe we're setting the seed. Maybe you're the one that did it. Yeah.

[B]

Yeah. I'd love to get some question marks going for my character.

[C]

Yeah.

[B]

Thank you so, so much for coming into the Hatch pillow fort. This was so fun. What an absolute trip. I love it, and I hope I dream of them tonight. Lana and Sister Mary Margaret, thank you so much for sharing your crime story with us, and thank you for being here. Good night, Deanna.

[C]

Good night, KP.

[B]

Sam.

[A]

To learn more about our phone free light and audio experience, head to Hatch Co. You can also follow us at Hatch Podcasts.