Transcript of Notorious Prison Breaks (Vol. 1)

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“Notorious Prison Breaks (Vol. 1)” was turned into text by HappyScribe’s speech recognition. Related tool: AI note taker.

00:00:00

Hey, weirdos. I'm Ash.

00:00:02

And I'm Alayna.

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And this is Morbid.

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This is morbid.

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What's up, Big Red?

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I'm exhausted.

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Period.

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We had a late over at our house last night where they— all the kids got to stay late.

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Those are all the rage these days. They are, because sleepovers are the worst.

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Yeah. Um, but it's still the same because everybody's exhausted.

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Yeah.

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And miserable, like really grumpy and not feeling well now 'cause they didn't get enough sleep.

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I used to be the worst after a sleepover.

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Yeah.

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I would be like, I don't feel good. Shut up. Don't talk to me.

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Yeah. That's essentially what's happening right now.

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Yeah. That's brutal.

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So that's what I'll return to after we record.

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I slept last night, but my body didn't get the message that it was sleeping, I think. It happens. I woke up and I was like, I was like, did I sleep?

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Did I though?

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Hello? And today I kind of just feel like I'm not here.

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Yeah, I'm not. My Oura Ring keeps telling me I have minor signs of strain.

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I had to stop wearing mine because I was getting too invested.

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I like it because it makes me— I think it's all in how you take it. 'Cause the way I look at it is that I'm not good at telling myself to slow down normally. But when I see it like that, I'm like, you should probably slow down.

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'Cause you know that you're affecting your body.

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'Cause I can see my heart rate. I can see— Like my sleep, I can see what it's affecting. So I think it's helping me to be like, hey,

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yeah,

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you got to chill out because like, I have like manifesting.

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I have such an addictive personality that I'll just go like way too far the other way and like change my whole life, like in a, in a ridiculous way.

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See, I'm just looking at it as like, hey, maybe don't have ice cream late at night and get more sleep.

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That's not the way to live though.

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No, I've— hey, it's working for me.

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Ice cream at night is the best.

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I love it at night, but only— but I was eating it way too late.

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Oh, okay.

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And then you're digesting all night.

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What's too late?

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They say you should like 1 or 2 hours before you're going to sleep.

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Oh, fuck.

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Probably 2 hours before you're going to sleep, which is valid.

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I made slutty brownies the other night.

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I love slutty brownies.

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Um, with like the pumpkin cookies, the Oreo, and then the brownie mix. And I had one of those with a scoop of vanilla bean ice cream at 9 PM.

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That sounds delicious.

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And then I went to bed probably at like 10 and had the worst heartburn of my life.

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There you go.

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Yeah, it's a lot of fucking chocolate to just directly lay down on your stomach. Just lay down. I turned over to Drew, I'm like, I have heartburn. He's like, yeah, I got it.

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I can't imagine from what. Yeah. It's crazy.

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It's like, that's so nuts.

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Yeah. And so it'd just be like that, you know?

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And here's the thing, I like to live my life that way.

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So. Living on the edge.

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It is what it do be.

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Yeah. I just like, I like having the control.

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Yeah.

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Of everything.

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Yeah.

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But I'm exhausted. And today we're gonna talk about, so this will be like a multi-parter, but not like back to back. It'll be something that we like, almost like a spooky road kind of thing. Like a series. kind of dip into every once in a while.

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Okay.

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We talked about doing notorious prison breaks before.

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Yeah.

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So I have 2 today

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that

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we're going to talk about, and then we'll talk about a couple more in a couple weeks.

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Okay.

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You know, we'll sprinkle them in.

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Yeah.

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You know, they're a fun little detour.

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It's always fascinating when people break out of prison.

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Because it's— there's true crime here.

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Yeah.

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There's fascinating prison life here.

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Fascinating prison life.

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Yeah. And then there's somebody escaping from fascinating prison life.

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Sounds like a TLC show.

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Fascinating Prison Life.

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Are you caught up on Fascinating Prison Life?

00:03:44

No, I'm not caught up on it yet.

00:03:45

Well,

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no. I don't know if I can return. It stresses me out. To prison? Yeah.

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Okay. I don't know if I can go back.

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I told you I'm tired. I'm also fully in draft writing right now, so my brain is a— Wasteland right now.

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Yeah, your brain, I would like to look at it.

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It's just got a lot of weird shit in it right now. A lot of weird research happening. Yeah.

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Um, let me cough.

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The way you said that was so aggressive. You were like, let me cough. Like I wouldn't let you.

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I really had to cough, and I was like, I have to do it now. So I was like—

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Let me cough.

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I meant to be like, let me cough, like don't say anything, but— Shut up. I had to cough.

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Let me cough.

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You can leave that in. Take the cough out, but— Leave that little back and forth in.

00:04:35

Oh, so let's talk about John Dillinger and his escape from Crown Point.

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I feel like I know him.

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You should.

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Yeah.

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He's pretty infamous. Yeah. I would say. Um, so we're gonna go back to the Dust Bowl. Oh, fuck. Let's go to the Dust Bowl. Um, so in the Dust Bowl-ravaged towns and villages scattered across America's mid and southwest during the Great Depression, few if any names were as notorious, feared, and revered as John Dillinger.

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Okay, Seuss.

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So, okay, poet. That's Dr. Seuss too. Um, don't forget about my MD.

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Oh yes, of course.

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So yeah, you should— you— I'm sure you've heard of John Dillinger.

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Yeah, I also think I learned— I like definitely learned about him, but I think we talked about him briefly on Crime Countdown.

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Yes, I'm sure we did. Yeah, yeah. So, as far back as his teenager years, Dillinger had been kind of doing the petty crime.

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Oh, okay.

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He was just in the crime, you know? Being an asshole. He was arrested a few times for minor thefts, you know, just getting drunk, getting in fights. After he was arrested for stealing a car in 1922, you know, those Roaring '20s.

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Oh!

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Can't stop him. He meant you can, actually. Like, the Great Depression's gonna stop him.

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It stopped him in their tracks, to be frank.

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He managed to avoid serious consequences. consequences by enlisting in the military.

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Ah, there it is.

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Uh, and he served 2 years before being dishonorably discharged in 1924 and returning home to Indiana, where he married his girlfriend, Beryl Hovius.

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Beryl? Isn't that fucking Kif's mom's name?

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Kif's mom's name.

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Shit. I never thought I knew another Beryl.

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Here you do. Here you do.

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Check that out.

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Now, despite leaving the Navy during a particularly strong period for the American economy, The Midwest, where much of the, you know, the agriculture industry was clustered, it was struggling even though the rest of the country was doing okay, um, due to post-war overproduction and declining prices.

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Ah, shit.

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That meant that while there was definitely jobs to be had in, like, urban areas, opportunities for good jobs were kind of scarce in small rural places like Indiana.

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Yeah.

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Like, like little towns in Indiana. Yeah. And Dillinger was kind of struggling to find stable work at this time. So he's frustrated. He's like, this is annoying.

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He's gonna crime again.

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He's out of options. Sometimes you just gotta crime, I guess. He's out of options. So he and his friend Ed Singleton, you know, they just robbed a local grocery store.

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I knew he was gonna crime again.

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He crimed again. And they were quickly arrested, of course, and convicted for that crime. And Dillinger and Singleton were sentenced to several years in prison for this robbery.

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Damn.

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But Singleton served just 2 years before being released.

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Okay.

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Now, at first, John and Beryl kept in touch through letters, and she would visit whenever she could.

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Romance.

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But the distance, you know, the prison distance, uh, and the long-term separation were a little too much for Beryl.

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They didn't get life after lockup.

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Yeah, they did not get that. And in June 1929, just 2 days before his birthday, she requested and was granted a divorce.

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Beryl!

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She said, I don't want to have to get you a birthday gift.

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Oh, damn. She said, times is tough.

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She did.

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She said, happy birthday, we're divorced. And

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he's in prison, so she's like, and I who?

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Fuck!

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Uh, when the news reached Dillinger, he was obviously devastated, and would go on to cite the divorce as one of the motivating factors for his crime spree.

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Men love—

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That eventually made him, quote, public enemy number one.

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Men love to blame women for everything!

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I was like, I don't know if it's so much her fault, as it is you doing crime and getting arrested and being in prison.

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It's probably that.

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I feel like that feels more like the fault. No,

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that was her fault too.

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Definitely her fault.

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Everything is Beryl's fault.

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Everything is Beryl's fault. So during his time in prison, he associated with several other known criminals, as one does.

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Yeah.

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Including bank robbers Harry Pierpont, Russell Clark, and Charles Mackley. To pass the time, they would just recount their stories of their successful heists. You know, they were kind of like those guys who talk about being quarterbacks in high school football.

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well past the age of high school.

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They're like, remember that time we robbed a bank? And you're like, yeah, I do, because you're in prison.

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Yeah.

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And they would plan future robberies that they hoped to carry out once they were released. They were dreaming big, you know?

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That's good to do in prison.

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Dreaming big. We're in prison now, but, like, let's keep crimin' when we're out.

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Yeah, perfect.

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Although he had been sent to prison for robbery, Dillinger's crime was nothing compared to the crimes of Pierpont, Clark, and Mackley. And it was through them that he learned the ins and outs of criminality that he would later use for his later crime spree.

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Dun dun dun!

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After serving nearly 10 years in prison for the grocery—

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His friend served 2.

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Yeah, for the grocery store robbery. He was released in May 1933, at the peak of the Great Depression. What a time to be released.

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Yeah.

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He had no wife, no job prospects, and he was a very bitter man with serious contempt for a society that he believed had done him wrong.

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Oh yeah, it's never your own fault.

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No. He He robbed a grocery store.

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Never, ever look within.

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No, never. No, never. Some introspection.

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Who does that?

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Don't do that. Having been released at, you know, arguably one of the worst periods in American history.

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Have you seen today?

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As far as the economy was concerned, at least. John Dillinger didn't bother investing much time in finding a job that he knew was not out there to be found. He's not wrong.

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Not there. Won't try.

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Instead, he found— he put his newly developed criminal skills to work. And in late June, just one One month after being out of prison, he robbed a bank in New Carlisle, Ohio, getting away with $10,000.

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Dang.

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10 times the average annual income for an employed American at the time.

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Holy shit.

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Yeah. Dillinger's success led him to begin immediately planning his next heist. This time, though, he was captured by police in Dayton, Ohio, and thrown in jail.

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I was like, did you even need to do another heist at that point? You got away with $10K, babe.

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It's like a gambler.

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Yeah.

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Like, they get that high and then they're like, I can do this again. Police seemed confident that the arrest put an end to his criminal career. But what they didn't know was that he had already devised a plan for what they would— what they would do should one of them get captured again, like the whole group of them. Now, in early August, Dillinger had convinced several former prisoners to smuggle guns into the cells of Pierpont, Mackley, and Clark, the 3 guys that he was back in jail with.

00:11:12

Okay.

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And several other prisoners, which they used to escape from prison.

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Damn, how do you smuggle guns into a prison?

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So the gang kept a low profile for a few weeks before settling— setting the second phase of the plan into motion on August 12th, 1933. Now, on that day, the men impersonated Indiana state troopers and convinced Ohio authorities that they were there to extradite John Dillinger to Indiana.

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Okay. Even though there was, like, no paperwork to say he was being extradited. Iconic.

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Now, unfortunately, when they conceived of the plan, it never occurred to the members of the gang that someone might, you know, like you said, want to see identification.

00:11:55

Yeah.

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Want to see some extradition paperwork. When they were asked for those very things by the local sheriff, Harry Pierpont shot the man to death and they escaped, taking Dillinger with them.

00:12:06

He shot the sheriff?

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He shot the sheriff.

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Damn.

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But he did not shoot the deputy.

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He did not. He just got JD.

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He did not.

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Fuck.

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Now free from jail, Dillinger and his gang spent the next 3 months robbing banks all over the Midwest.

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Fun!

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They got him out. They busted him loose at a time when organized crime was on the rise in America, and career criminals like, oh, I don't know, Al Capone. Heard of him. Lucky Luciano. Your guy. They were becoming folk heroes at this point.

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Yeah.

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Dillinger and his gang immediately caught the attention of the press and became household names. their pictures plastered on the front pages of newspapers everywhere. And although the men enjoyed the notoriety, because obviously the press coverage ultimately proved to be kind of a hindrance for their criminal careers, it's like, not great. Yeah, you don't want to be like—

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you don't want to be notorious with your face in the papers when you're robbing banks.

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While you're criming, you know? In late January 1934, 2 firefighters in Tucson, Arizona recognized the group when they were escorting guests out of a hotel during a small fire.

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Dang.

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They'd seen their photos in a magazine of detective stories. that they'd been reading earlier in the day, and they were like, hey, that's John Dillinger and his gang.

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Hey, I know you.

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The firefighters reported the sighting to police, who immediately traced the Dillinger Gang from the hotel to a nearby rental home where their luggage had been sent after the fire.

00:13:26

Wow. So they were, like, kind of dumb.

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Yeah. Tucson officers devised a plan in which one officer would go to the door claiming to be lost and looking for an address he was unfamiliar with. After confirming the men were inside, police would rush the house and arrest the gang. Not a bad plan, you know, as those plans go, I would say. Yeah. But it didn't work out that way.

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Okay.

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Not at all. As soon as the door was opened, Russell Clark assumed the man at the door was a police officer and rushed at him.

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Good.

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Just right away.

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Good.

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While a woman in the house quickly slammed the door before the other officers could even get inside.

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Shit.

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And when she slammed the door, she crushed one of the officers' fingers in the process. Inside, Clark and the undercover officer, Chet Sherman, fought over Sherman's gun. wrestling one another all over the living room and an adjacent bedroom. Clark finally managed to draw his own gun and point it at Sherman, the police officer. But by then, the other officers had made their way inside and subdued Clark. Later that day, police arrested Dillinger, Pierpont, and Mackley— or Markley. But— or no, it is Mackley. Sorry. I thought I was being very too Boston.

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No, no, you're good.

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But the rest of the gang managed to get away.

00:14:34

Oh, wow.

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Now, in a statement following the arrest, the Commissioner of Public Safety, Alfini, Fine.

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There

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it is. Uh, told reporters, it is a great relief to the state to have these desperados in custody. Like all so-called bad men, they apparently folded up when they were overwhelmed. They quit when they did not have the upper hand. Those desperados.

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Dang. I'm like, most people do quit when they don't have the upper hand.

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And I love that he was like, they're little bitches.

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That is kind of funny.

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That's essentially what he said.

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He said, fuck 'em.

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A few days later, Dillinger and the others were extradited to Indiana to stand trial for 10 bank robberies across the state, which netted them nearly $250,000.

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Yeah, so they did not need to keep doing this.

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No, they were gluttonous.

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Just fucking cut that money and run.

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Gluttony. Now, on the trip back to Indiana, Dillinger spoke freely with their detective escorts. Um, he told them before freely confessing to the robberies, there's no use denying anything now. I mean, might as well.

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You are caught red-handed.

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To the officers in the escort party, he appeared to be in fear of spending the rest of his life in jail, so he confessed in the hope of leniency.

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Okay.

00:15:57

Now, uh, one of the detectives told a reporter, Dillinger is convinced that he's going to burn, and so he's talking. Of course, John Dillinger was not the kind of man to fear prison, having spent a lot of his life already there.

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Yeah.

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And what the detectives recognized as defeat and desperation was, in fact, bravado and a lot of confidence.

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Okay.

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All 4 members of the Dillinger Gang were placed in separate cells in the Lake County Jail in Crown Point, Indiana, where they were awaiting trial. For more than a month, Dillinger was kind of a star in the jail. where reports from all over the country were desperate— or reporters were desperate to interview him.

00:16:34

Yeah.

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Since his incarceration, the local police had touted the jail as, quote, escape-proof.

00:16:40

Oh, that's like calling the Titanic unsinkable.

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The unsinkable ship. But on March 3rd, John Dillinger proved them wrong.

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I had a feeling.

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That morning, Deputy Sam Cahoon—

00:16:51

Great name.

00:16:51

I know. Arrived in the cell Dillinger shared with another inmate, Herbert Youngblood.

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Herbert Youngblood.

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Whose turn it was to mop the cell in the hallway. Now, Cahoon set the bucket of soapy water down on the floor and called out to Youngblood. But when he straightened up, he found himself looking down the barrel of a pistol held by Dillinger, who instructed him to unlock the door.

00:17:13

Have you looked up a picture of John Dillinger?

00:17:15

I don't think I have.

00:17:16

He is exactly what you think.

00:17:18

Show me this man. Oh, oh yeah, I've seen that.

00:17:21

He's exactly what you think.

00:17:23

That's— I've seen that picture.

00:17:24

Yeah.

00:17:25

Honestly, good for him. Yeah. Good for him having that kind of smirk with what he's

00:17:29

done. He's really killing it.

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I'm kidding, everybody. Yeah, it's a joke. I know he's a bad guy. Yeah. Just got to make sure.

00:17:38

Also, it looks like he has spiderwebs on his tie.

00:17:41

Maybe he does.

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Don't those look like spiderwebs?

00:17:44

It does, actually. He's got a very cleft chin.

00:17:46

Yeah, he got a booty chin.

00:17:48

No, outside—

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And I can say that because I have a booty chin.

00:17:50

No, outside the door that led to the cells, The civilian cleaning detail was finishing up their work for the morning, and Dillinger politely rounded them up and locked them in his former cell.

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Oh my God.

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Then he nodded to Cahoon, indicating that he was to be his hostage. He was like, come with me.

00:18:07

Oh no.

00:18:08

From there, Dillinger went through the jailhouse slowly, rounding up all the deputies and the warden, taking their guns before locking them in the cells.

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And the warden? The fuck?

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Inescapable, this jail. Before leaving the jail, Dillinger grabbed 2 silver submachine guns from the warden's office.

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Oh my God.

00:18:28

Once they were outside, he located the nicest car in town, a brand new Ford F8— or V8 that belonged to none other than Sheriff Lillian Hawley, and took it and drove off towards Chicago.

00:18:40

Wow.

00:18:40

So he escaped the inescapable jail.

00:18:44

Yeah.

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Took 2 silver submachine guns—

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That belonged to the warden.

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And then stole the sheriff's brand new car.

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I mean...

00:18:53

I

00:18:53

mean... You gotta do that thing that kids do where they tap their fingers.

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You gotta do that tapping the finger thing.

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I'm like, I know it's wrong, but, like, that's temptation.

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I'm not encouraging it. It's just hearing it now. So many years later.

00:19:06

Yeah, don't try this at home.

00:19:07

Don't do that. Now, the news of Dillinger's escape came as a shock to some and a delight to others. Yeah. Especially those who'd come to see the man as kind of a Depression-era hero.

00:19:16

I mean...

00:19:17

But to Lily and Holly, the sheriff and the deputies at the jail. It was a national embarrassment.

00:19:23

Uh, yeah, I'd say so.

00:19:24

Holley had colorful things to say. He said, if I ever see John Dillinger, I'll shoot him through the head with my own pistol.

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Do you still have your pistol? I said, did he take it though?

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Is it in your car?

00:19:35

What if he shoots you with your own pistol?

00:19:37

Of course, the question on everyone's mind was, how had he managed to escape from a supposedly escape-proof prison or jail? There's some debate about how Dillinger managed to execute this escape from Crown Point, but most everyone agrees it starts with Dillinger's lawyer, notorious mob lawyer Louis Paquette. With his trial scheduled from March— for March 12th, there was a good chance Dillinger would be found guilty and executed for the death of a police officer that occurred during one of his robberies.

00:20:07

Okay.

00:20:07

A few days before the prison break, Paquette paid a visit to his client where it's believed he either slipped him a wooden gun Or he gave him the tools to whittle it himself. Yes, you heard that right, it was a fake gun.

00:20:21

A wooden gun?

00:20:23

Once Dillinger had carved the gun, or received it, he painted it black with shoe polish.

00:20:28

Stop.

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And no one could tell the difference.

00:20:31

Stop it right now.

00:20:32

It should be said that while the wooden gun is the widely accepted version of events, there are some who believe that he gave him a real gun.

00:20:39

Okay.

00:20:41

Either way, once he forced the deputy to open the cell, he took the man's weapon and was legitimately armed at that point. But this could have started with a wooden gun.

00:20:48

That's insane.

00:20:49

Yeah. Now, with Dillinger on the run, the sheriff formed a massive posse and began the hunt for the escaped criminal, who had by then already traveled across the state line into Illinois and on to Chicago.

00:21:01

I love to think— I love to think of the sheriff just, like, running deep with his posse.

00:21:05

Right?

00:21:05

Just deep. He's formed a posse.

00:21:07

Deep with his posse.

00:21:08

Like the Pussycat Dolls.

00:21:09

Well, and on the way to Chicago, he picked up his girlfriend, Billie Frechette. Okay. Dillinger did.

00:21:15

Okay.

00:21:15

In doing so, he violated the Federal Motor Vehicle Theft Act, which puts his escape into the jurisdiction of the FBI, who wasted no time mounting their search for him. Now, following his escape, he and Frechette, his girlfriend, traveled to Minneapolis, where they set themselves up in an apartment, and Dillinger began assembling a new gang that included his old fellow prisoners, John Hamilton, Homer Van Meter, and new acquaintance Lester Gillis, better known as Baby Face Nelson.

00:21:44

Oh my God.

00:21:45

In the 3 months that followed, Dillinger and the new gang robbed several more banks across South Dakota and other parts of the Midwest.

00:21:52

It is remarkable that they still were able to pull off these robberies. Yeah. Keep going. Like, it's not good, but I'm just like, holy shit.

00:21:58

It's pretty remarkable. Dillinger's reign finally came to an end on July 22nd, 1934. when federal agents tracked to Chicago's Biograph— tracked him to Chicago's Biograph Theater, and a shootout ensued. In the firefight, Dillinger was shot 4 times, with the fatal bullet entering the back of his neck and traveling into his brain before exiting just under his right eye. Ooh.

00:22:23

I mean, how do you think that's gonna end?

00:22:27

Yeah.

00:22:27

I think those— I think criminals like him just live so fast.

00:22:31

Oh, yeah. They just know that it's gonna end in a blaze.

00:22:33

And I don't even think they, like— like, think of it.

00:22:36

Yeah. You know? Well, I think they just don't care. They're gonna— they're here for a good time, not a long time. Yeah. Is their straight-up motto. Truly. Like, I really think that.

00:22:44

And I think they think that they'll outsmart everybody.

00:22:46

Yeah, they always think they're smarter.

00:22:48

That's an insane story.

00:22:50

Yeah. Now, given that John Dillinger was able to walk out of the Lake County Jail by simply wielding possibly a wooden gun, it's hard to take their claims of an escape-proof prison very seriously.

00:23:00

Yep.

00:23:01

But about 2,000 miles to the west, There was another prison where the claims of being escape-proof were considered by most to be entirely accurate.

00:23:09

Okay.

00:23:10

Established in 1859 as a military prison, Alcatraz Penitentiary was transitioned to a civil— civilian federal prison— prison, goddamn— in 1933.

00:23:22

Yeah, I think I've heard of it.

00:23:23

And it was almost immediately America's most notorious prison.

00:23:27

Yeah.

00:23:28

It housed some of the nation's most infamous criminals, including Al Capone.

00:23:32

Yup.

00:23:32

George Machine Gun Kelly Barnes.

00:23:34

My distant relative.

00:23:35

Yep. And Alvin Creepy Karpis Karpovitz.

00:23:39

Yup.

00:23:40

Situated on an island about a mile and a half from the shore in San Francisco, Alcatraz was an entirely self-contained penal system that was, because of its location, believed to be escape-proof. When the federal government took over operation of the prison in the early '30s, it was with the intention of housing notorious gangsters and acting as a deterrent to the crime wave that had really gripped the country at that point. In addition to the high number of guards relative to the number of inmates, the cell blocks were not positioned against an outer wall, meaning that even if a prisoner was able to get through the cell wall, they would still be inside the prison.

00:24:17

That's crazy.

00:24:18

And also, in the highly unlikely event that the prisoner somehow managed to get through the walls and walls and then past the guards and over the razor wire fences, San Francisco Bay still presented a pretty insurmountable problem.

00:24:31

I was gonna say, you are surrounded by water.

00:24:33

Yeah. Not only is the water freezing cold and prone to strong, fast currents, but the area is also home to several species of sharks.

00:24:41

Yeah.

00:24:41

Making it almost impossible for someone to successfully swim across.

00:24:45

Which is so interesting, 'cause sharks usually like warm water, don't they?

00:24:47

Yeah. I guess so. I don't know. I don't know if they're different, like, species.

00:24:51

Different species, yeah.

00:24:52

Now, despite the odds being very much against a successful jailbreak, In its 29 years as a federal prison, 36 prisoners attempted to escape on 14 different occasions.

00:25:02

Damn.

00:25:03

In nearly every case, they were either captured or shot down before they even reached the water. And those that managed to get to the bay were later determined to drown. But there is one case in which 3 escapees not only made it to the water, but were able to get away from the prison and remain unaccounted to— for to this day.

00:25:22

That's insane to me.

00:25:24

This one's crazy. So born and raised in Georgia, John and Clarence Anglin had a pretty difficult childhood. As 2 of 13 children— Holy shit. Born to seasonal farm workers, their early lives were just full of chaos, a lot of poverty. They were dragged from one place to the next as their parents searched for work. By the time they were in their early teens, John and Clarence had begun engaging in— Petty crime. Exactly. Petty crime. And within a few years, they graduated to Bank robbery.

00:25:53

Big crime.

00:25:54

Bigger crime. And in January 1958, they were arrested and sentenced to 35 years at Leavenworth Penitentiary.

00:26:01

Fuck.

00:26:02

From the moment they arrived at Leavenworth, the Anglin brothers began scheming a way to escape, including one escape attempt in which the brothers hid inside a large bread box and covered themselves with bread loaves that were to be transported out of the prison.

00:26:16

And that is how I would like to escape from prison should I ever enter.

00:26:20

The brothers' attempt was almost successful. The box was loaded onto the truck and almost made it out, out of the prison grounds. But then the unusually large shipping container caught the eye of a supervisor who stopped the truck and checked the cargo and found John and Clarence inside.

00:26:37

Said, hey, you're not red.

00:26:38

Both men were returned to their cells, but tired of their repeated attempts to escape, the warden had them transferred to the one prison he knew they could never get away from.

00:26:47

He said, fuck y'all.

00:26:48

Alcatraz. You're going to Alcatraz. It was at the prison that John and Clarence met their future co-conspirator, Frank Morris. Like the Anglin brothers, Morris had been a criminal for pretty much all of his life. Orphaned at age 11— Oh. When his mother handed him over to the foster system, Morris spent 7 years bouncing from one foster home to another until he was finally discharged on his 18th birthday, by which time he had already been arrested for a variety of crimes, from Narcotic possession to robbery.

00:27:17

Yeah.

00:27:18

In April 1955, Morris was sent serving a 10-year sentence at the Louisiana State Penitentiary, which is also not to be ignored.

00:27:26

Not to be fucked with.

00:27:27

For robbery. When he and another inmate managed to escape that prison, the 2 convicts managed to hitchhike to Baton Rouge, then made their way to New Orleans, where they laid low for a few months. In that time, they planned and eventually executed a robbery of a bank in the nearby town of Slidell. Then they fled the state for Kansas City, Missouri. Now, having made it out of the state, it's possible Frank Morris could have stayed free. But after a year on the run, he robbed a bank in Kansas City and was eventually arrested.

00:28:00

That'll do it.

00:28:00

Serving time in the Missouri prison before being sent to Alcatraz in January 1960.

00:28:06

Okay.

00:28:06

Now, it's unknown who actually planned the escape. But what is clear is that it was not an impulsive act. It was a long time coming, very much in the works before they made the ultimate break.

00:28:19

I mean, you would have to plan that forever to be successful.

00:28:22

A few weeks after arriving in Alcatraz in January 1960, Frank Morris was moved to B Block and placed in a cell next to Allen West, a criminal with a very violent past. For at least a year, Morris, West, and John Anglin began talking about how they might go about escaping. After one of the other prisoners told Morris a story about a former prisoner finding a ventilation shaft in B Block that led all the way to the roof. So they were like, after hearing about that, they were like, this is possible. I think we can get out of here. If they had been planning to make the break earlier, their plans were interrupted when West was thrown in solitary confinement for a bit after orchestrating a small riot during which one of the other prisoners was stabbed.

00:29:05

Oh, fuck.

00:29:05

By the time West was released from solitary in early 1962, Clarence Anglin had been transferred to B Block, and there was no way John would leave his brother behind.

00:29:15

Yeah.

00:29:16

Now, over the course of 6 months, the 4 men used spoons, old saw blades, and any other metal items they could find to dig through the wall of their cells to reach the ventilation shaft on the other side of the wall.

00:29:28

I fear we can't move past the fact that as prisoners, they had access to saw blades.

00:29:32

Old saw blades.

00:29:34

Old saw blades. Where'd you guys get those? Yeah. Hello?

00:29:37

Now, what's funny about this is you're probably like, didn't anyone hear them digging through a wall?

00:29:42

You would think, especially a saw.

00:29:44

West would play the accordion to cover the noise of digging.

00:29:48

Iconic.

00:29:49

Yeah. So he gave him an accordion. I don't know.

00:29:53

I would think that in, like, prison, that would be the last thing that you would have is an accordion.

00:29:57

I don't know.

00:29:58

I mean, I've never been.

00:29:59

I've never been. I don't know if they— maybe they hand you one when you come in. Do something. During the day, when they weren't confined to their cells, they covered the hole in the wall with thin pieces of cardboard that had been painted to resemble the wall.

00:30:12

They had access to so many materials.

00:30:14

They were illusionists. They were mind freaks.

00:30:16

They were illusionists.

00:30:17

They were mind freaks as well. After several months of digging, they'd widened the hole enough so they could get through into the shaft. When they climbed a large pipe up to the top floor of the cell block, which was not in use at the time. Having more space to move, they used the abandoned portion of the cell block to construct a raft and life preservers out of dozens of raincoats and other waterproof items they'd managed to collect over the course of 6 months.

00:30:45

This is like a weird, like, I Spy collection.

00:30:48

It is. Now, given the high security of the prison and the frequency with which the guards did their rounds and checked the prisoners in their cells, it seems entirely impossible that 4 men could have tunneled out of their cells night after night.

00:31:13

Yeah.

00:31:13

And their absence wouldn't have been noticed by the guards. You're probably like, no.

00:31:17

Maybe they were buddies with the guards.

00:31:19

They were going up every night. No way were they— nobody's homies with the guards at Alcatraz.

00:31:24

No.

00:31:25

It was only later, after they escaped, that prison officials realized the men had used plaster heads made lifelike with painted faces and hair contrived from the bristles of paintbrushes to disguise their absence.

00:31:38

I remember this. That's—

00:31:41

Straight up, like, made little mannequins of themselves.

00:31:45

They were crafters.

00:31:48

Crafters at heart.

00:31:49

Crafty bitches.

00:31:50

Truly crafters at heart. In another time, given, given somebody sitting them down and being like, let me really tell you what you're good at, they could have had Etsy shops.

00:31:58

Bitch, they would kill at Flea Market Flip.

00:32:00

They would.

00:32:01

Wow.

00:32:02

A farmer's market? Get out of here.

00:32:03

Lara Spencer would love them.

00:32:05

Yeah. But no, they had to do this. Now, using paint from the maintenance department and discarded hair from the barbershop, they each constructed the base from papier-mâché. They were using papier-mâché and designed them in each of their likenesses. Like, so they both had a special project of, like, making their own likenesses.

00:32:24

Rafty kings.

00:32:25

In the dark, with the blankets pulled up tight around the necks of the dummies and the heads slightly obscured by the pillow, the guard on the other side of the cell door couldn't tell that it wasn't a person. It just looked like someone sleeping.

00:32:36

Oh my God.

00:32:37

Yeah.

00:32:38

They, like, lowkey deserved this escape.

00:32:40

They kind of did.

00:32:41

I'm going to go on record.

00:32:42

I'm not saying they're good guys, but they kind of— they did their big one with this.

00:32:46

They really worked for it. I'm like, damn, just He's like, look, go into the arts!

00:32:49

Use it for good!

00:32:50

Go into the arts, brothers! Now there's—

00:32:52

on the evening of June 11th, 1962, just after lights out was called at 9:30 PM, the men put their plan into motion.

00:32:59

Period.

00:33:00

Once the guards were out of sight, Frank Morris and the Anglin brothers piled clothing and towels under the blanket and placed the papier-mâché head on the pillow.

00:33:08

Also, like, did we not do cell checks back then?

00:33:10

No. Then they disappeared into the hole that led to the ventilation shaft. West had planned to do the same, but when he went to crawl through the hole, he discovered that the temporary plaster he'd used to obscure the damage to the wall had hardened, and the hole was now too small for him to climb through.

00:33:27

No!

00:33:28

Now, unaware that Allen West was stuck in his cell and not wanting to waste any time, the 3 men climbed up the drainpipe— so they just abandoned him— in the ventilation shaft until they reached the exhaust fan that led outside to the roof. Using tools stolen from the machine shop, they removed the bolts that secured the fan and were able to access the roof of B Block. Then they shimmied down a kitchen vent that led to the prison yard. Under the COVID of darkness and carrying their makeshift raft, the 3 men somehow managed to make it across the yard and over 2 large fences topped with razor wire before they reached the northeast edge of the island.

00:34:10

This is bonkers.

00:34:11

Using a concertina borrowed by another inmate, which they'd fashioned into a kind of makeshift pump, the 3 men inflated their raft, donned their homemade life jackets, and set off from Alcatraz Island.

00:34:25

And they left their homie.

00:34:27

They left their homie. By the time Allen West managed to get through the hole in the cell wall and climb up to the shaft to reach the utility room where the boat had been constructed, The other 3 were long gone.

00:34:38

Oh, that's so sad.

00:34:39

They just left him.

00:34:40

Why do I feel so bad for this criminal?

00:34:42

There's no loyalty here.

00:34:43

No.

00:34:43

In the room, he discovered that they'd left behind materials that he could use to make his own escape. But when he finally made it to the roof of the cell block, the enormity of what he was doing washed over him. And terrified to make the run on his own, he climbed back down the ventilation shaft and returned to his cell.

00:35:00

He said, you know what? Prison is all right.

00:35:02

He said, I'll just stay here.

00:35:03

Damn.

00:35:04

Now, at 7:15 AM, a guard dog doing— or a real guard. I don't know why I said guard dog.

00:35:11

A guard dog?

00:35:12

I'm tired. A guard doing his rounds approached Frank Morris's cell and attempted to wake him. When Morris didn't move from his bed, the guard stepped closer and noticed that something about Morris's head seemed off.

00:35:24

He was like, fuck, this guy's real sick.

00:35:26

The guard stuck his hand through the bar and touched the head that lay on the pillow. And his heart sunk when he realized it was nothing more than papier-mâché.

00:35:33

Oh, no.

00:35:34

Pulling his hand back quickly, the head rolled off the bed and landed on the floor.

00:35:38

Stop it.

00:35:39

A piece of the nose breaking off in the process.

00:35:41

Stop it.

00:35:42

He broke his project. It was in that moment that the jailbreak was discovered and the alarm was sounded across the entire 12-acre prison. The news of the escape made national headlines from coast to coast, even occupying a primetime spot on the COVID of the New York Times. I

00:35:56

mean, I would think.

00:35:57

It was not as though no one had ever heard or had ever attempted to escape the escape-proof Alcatraz before, but it was the first time anyone had succeeded. And when he was asked whether he believed the men were still on the island somewhere, Warden Allen Blackwell exasperatedly replied, I don't know. I just don't know.

00:36:17

He's like, you know what? Fuck them.

00:36:19

He's me this morning. He was like, I don't know. Maybe. I love that they're like, do you think they're still on the island? He's like, fuck if I know, like, I don't give a shit.

00:36:29

He's like, I don't know, did you see their fucking project? Fucking nasty as hell.

00:36:32

A few hours later, and after the entire island had been searched by a massive team of law enforcement officials and dogs— dogs were there, dogs came back— Blackwell's opinion changed, and he reported that he was, quote, virtually sure they were off the rock.

00:36:47

Fuck.

00:36:48

Oh, like, you don't say.

00:36:49

Thanks, Warden.

00:36:50

Details of the escape were quickly ascertained when Blackwell and the investigators questioned Alan West. Ohhhhh. Who claimed the plan had been devised by Frank Morris. He was like, I didn't do it. As for what could have happened to the men once they left the island, no one knew. That night, the current was moving at 2.7 knots, which meant that even in a raft, the 3 men would have struggled considerably to navigate their way to shore.

00:37:14

Okay.

00:37:15

In their search of the area, the authorities found no sign of the raft or any evidence of the men in the water or on land.

00:37:21

Huh.

00:37:22

In the days that followed, countless tips were called in from citizens who, of course, believed they had seen Morris and Anglin. But none amounted to anything more than really mistaken identity. In the meantime, questions began to roll in as how 3 prisoners had managed to execute this crazy elaborate plan and escape, again, escape-proof Alcatraz.

00:37:45

Right.

00:37:46

The biggest factor, it seemed, was the age of the prison itself. In addition to being more than 100 years old and having not really had any major repairs in, like, decades, exposure to the elements and the saltwater, because it's on an island, had weakened much of its infrastructure.

00:38:03

That makes a lot of sense.

00:38:04

Blackwell said, I would say erosion made the escape easier. How much easier? I don't know. Again, I don't know.

00:38:10

Yeah, who knows?

00:38:11

He just doesn't know. The authorities searched for the 3 escapees for months, but aside from one of the oars and a makeshift life preserver found floating in the bay, which does tell me something.

00:38:21

Yeah.

00:38:22

There was— there wasn't any other sign of Morris or the Anglins. And in time, the escape from Alcatraz achieved legendary status, inspiring novels and films and becoming one of San Francisco's most enduring mysteries.

00:38:34

Do we think they died?

00:38:35

I don't know. The Marshals Service spokesman Dave Branham said, although we never found the bodies, we presume they've drowned. But we think they— but we think there is a possibility they're alive.

00:38:47

Okay.

00:38:48

So they're kind of like, it could go either way.

00:38:50

Yeah. I mean, those are the 2 possible outcomes.

00:38:52

Those are— they either died or they lived.

00:38:53

Yeah. It's crazy.

00:38:54

I'm like, so they're not in purgatory. Okay, got it. Uh, they're not in a state of like arrested development. No.

00:39:00

Like, he's like, they actually got trapped in a parallel universe.

00:39:03

He's like, this isn't a Twilight Zone episode. But, uh, that was in 1993. And apparently, like, according to the FBI website, there was a plan they thought where they were gonna like rent a car or steal a car. Okay. Once they got off the island.

00:39:17

Yeah.

00:39:17

And that's how they were going to escape. And there was no reports in the area of cars being stolen in the area or a rented car.

00:39:24

Rented cars. What, at that time? 3 prison escapees.

00:39:26

Also, if you go on the FBI website and look up this escape, they show you a picture and we'll post a picture of it if, if like, you know, because that's easier.

00:39:36

Yeah.

00:39:36

You don't have to go to the website, I guess.

00:39:38

Yeah, we'll post it.

00:39:38

I'm like, you know what? That's easier as I spoke.

00:39:40

I was like, you know what?

00:39:41

We just will. I'm just going to do that. There's a picture of the, like, plaster, the papier-mâché heads That's crazy. When I tell you they were artistes. Like, I'm thinking— Couldn't be me. I couldn't have made that good of a plaster head, I don't think.

00:39:57

I'm also just like— That was really good. You guys could have found careers.

00:40:00

That was straight up hair.

00:40:01

Yeah.

00:40:01

Like, they collected from the barbershop. And also, if you've ever watched Syfy's Face/Off, you know how hard it is to lay hair on, on a, like, makeup.

00:40:11

Yeah.

00:40:12

They laid hair. That looked real.

00:40:14

Good for them.

00:40:14

I was impressed by that.

00:40:16

They were determined for the cause.

00:40:18

They were, but—

00:40:19

I kind of hope they lived.

00:40:21

It would be—

00:40:22

I don't think they did, but—

00:40:24

I know. I don't know. But damn, it would be crazy if they did.

00:40:28

I mean, you never know. Crazier things have happened.

00:40:30

Well, the investigations into the escape exposed the considerable administrative and structural problems at Alcatraz, all of which would have required considerable money to fix.

00:40:40

Yeah.

00:40:40

And on March 21st, 1963, the prison was closed for good.

00:40:44

Dang.

00:40:45

In the years since, it's become a national public park and a popular tourist destination.

00:40:50

And it's supposedly haunted. Oh,

00:40:51

it is. As for Frank Morris and John and Clarence Anglin, they were never seen or heard from again.

00:40:58

Crazy.

00:40:59

The Anglins' sister, Mae Widner, said in 2012, I've always believed they made it, and I haven't changed my mind about that.

00:41:06

Aww.

00:41:07

And she isn't alone. When asked whether he believed the prison escape was successful, U.S. Marshal Mike— uh, Michael Dyke replied, we have to operate under the assumption they made it.

00:41:17

I mean, hey, that's a U.S. Marshal, so—

00:41:19

And they're saying, like, yeah, that's probably—

00:41:21

I mean, they didn't find their bodies, but—

00:41:23

They got off the island.

00:41:24

Also, sharks.

00:41:26

That's the thing.

00:41:27

You know?

00:41:28

Yeah, like, logic tells me they didn't, but—

00:41:32

Yeah.

00:41:32

But my whimsical nature tells me that I would like them to have made— then again, they're bad guys, so it's not like that we're— we're We're sitting here being like,

00:41:41

but you know

00:41:41

what, maybe they made it. And I'm like, but, oh, I guess if they did make it, they didn't really cause a stir after that.

00:41:47

That's the thing. They rehabilitated. And here's what I think happened. They opened up a studio altogether and they taught pottery and papier-mâché and fucking art.

00:41:58

If you're in the San Francisco— if you're in that area and you took art classes around the city—

00:42:03

It's an artsy area.

00:42:04

And you had your life transformed by your art teacher, Look at that. That our teacher was one of these guys.

00:42:10

It was. They became art teachers.

00:42:12

And that's a fact. So.

00:42:15

So do with that what you will.

00:42:17

So you're welcome.

00:42:18

So put that in your pipe and smoke it.

00:42:20

It's true.

00:42:20

I'm obsessed. I think they were mostly just like bank robbers, right?

00:42:24

I think so.

00:42:25

Like, I'm not telling you to go rob banks.

00:42:26

I think their bank robberies included— Moita. Guns and moita sometimes.

00:42:31

Okay, well, I don't condone that.

00:42:33

But then they made craft

00:42:35

Crafts.

00:42:35

And they were your art teacher,

00:42:37

period.

00:42:37

They changed your life.

00:42:40

I want to do— I've never done papier-mâché.

00:42:42

I've never done—

00:42:43

I saw this girl on TikTok and she made the coolest papier-mâché pumpkin head.

00:42:49

Hell yeah.

00:42:50

I'm gonna find it and send it to you later. I want to do— and I'll shout her out once— hell yeah, once I find her. But I, I'll never find her. I'm on TikTok far too frequently. Um, never find her right now.

00:42:59

If it's you, Let us know. Did you make a really cool pumpkin head out of paper mache?

00:43:03

It was like vintage.

00:43:04

Oh yeah.

00:43:05

Somebody tag me in it so that I can shout them out.

00:43:07

Do

00:43:07

it, please.

00:43:08

Do the work.

00:43:09

Do the work for me so I don't have to. No, I just— I— if I tried to pull up a TikTok from—

00:43:14

yeah, it couldn't be me.

00:43:15

It's bad. I have a scrolling problem. I probably am going to get carpal tunnel. Anyways, we hope you keep listening.

00:43:21

And we hope you

00:43:22

keep

00:43:23

it weird.

00:43:25

But not so weird that you don't get super crafty if you go to prison and reform your life. and become an art teacher.

00:43:31

Yeah.

00:43:32

Bye.

00:43:32

They were your art teacher.

Episode description

For as long as human beings have been locking one another up in cages or dungeons, there have been other human beings scheming and strategizing ways to escape their cells and break free of their prisons. More often than not, their attempts prove futile and they’re recaptured, their punishments extended and the conditions of their surroundings made worse. But in their experiences with freedom, however brief they may be, the escapee becomes legendary, their exploits going on to be told and retold in books, films, and songs long after the prisoner has passed away. While some prison breaks—like those of the wrongfully incarcerated or unduly punished—can be justified and go on to be romanticized, others are less romantic or exciting and can even lead to deadly outcomes. And yet, no matter the circumstances and outcomes, each one can tell us something about the system and culture responsible for the initial sentence and subsequent escape. Here is the first volume of this fascinating subject!ReferencesAssociated Press. 1986. "Supervisor apparently kidnapped by escapee." Ann Arbor News, December 6: 1.—. 1962. "Alcatraz 'age' held factor in trio's escape." Los Angeles Times, June 14: 5.Frishman, Dan. 1962. "Big Bay manhunt on for three Alcatraz escapees." San Francisco Exminer, June 13: 1.Hanson, Tom. 2023. Prison escapes in America: How common are they and what's the real risk? September 18. Accessed September 12, 2026. https://www.cbsnews.com/news/prison-escapes-in-america-how-common-are-they-and-whats-the-real-risk/.Hotz, Mark. 2012. "Awaiting trial Dillinger escapes." Bank Note, June: 10.Indianapolis Star. 1934. "Dillinger, 3 state felons caught." Indianapolis Star, January 25: 1.—. 1934. "Expecting death, prisoner tells of crime career." Indianapolis Star, January 31: 1.—. 1934. "Vast army hunts John Dillinger." Indianapolis Star, March 4: 1.Kinkopf, Eric. 1987. "Escape." Detroit Free Press, January 2: 16.Leff, Lisa. 2012. Escape from Alcatraz: 50 years later, mystery remains. June 12. Accessed September 9, 2026. https://www.nbcnews.com/id/wbna47782343.Martindale, Mike. 1987. "Escapee murders way across country." Burlington Free Press, June 14: 1.New York Times. 1962. "3 Alcatraz convicts cut their way out with spoons." New York Times, June 13: 1.—. 1962. "3 Alcatraz convicts cut their way out with spoons." New York Times, June 13: 1.Press, Associated. 1986. "Police say Ypsi center worker adits he aided man's escape." Herald-Palladium (Benton Harbor, MI), December 26: 17.Richardson, Randi. 2021. Beryl Hovious and Public Enemy No. 1. March 22. Accessed September 8, 2026. https://monroehistory.org/2021/03/22/beryl-hovious-and-public-enemy-no-1/.Swickard, Joe. 1987. "Suspects in deadly tales." Detroit Free Press, January 22: 1.Warren, Jenifer. 1993. "Escape from Alcatraz?" Los Angeles Times, November 11: 3. 
Cowritten by Alaina Urquhart, Ash Kelley & Dave White (Since 10/2022)Produced & Edited by Mikie Sirois (Since 2023)Research by Dave White (Since 10/2022), Alaina Urquhart & Ash KelleyListener Correspondence & Collaboration by Debra LallyListener Tale Video Edited by Aidan McElman (Since 6/2025) Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.