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Notorious Prison Breaks (Vol. 1)

45m 4s

Notorious Prison Breaks (Vol. 1)

The transcript explores two legendary prison escapes: John Dillinger’s breakout from a mid-1930s Indiana jail and the 1962 escape of Frank Morris and the Anglin brothers from Alcatraz. Dillinger used a fake wooden gun to overpower a deputy, escaping after a short prison term and launching a criminal spree across the Midwest, only to be captured and later killed. His escape underscores the fragility of perceived security. Meanwhile, the Anglin brothers and Morris, inmates at Alcatraz, meticulously planned a complex escape over months, tunneling through a prison wall and creating convincing paper-mache dummy heads to hide their absence. They reached the island’s edge and fled by raft, only to vanish without a trace. Though authorities declared them lost, some officials and family members believe they survived. The story highlights not just criminal daring but also profound creativity—transforming from bank robbers into artisans and art teachers. These narratives reflect on the resilience of the human spirit, the limits of institutional control, and the enduring mystery of what happens when people break free. The accounts emphasize how ingenuity, artistry, and the will to survive can rewrite not just lives, but legends.

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English
Hey, weirdos, I'm Ash, and I'm Elena, and this is morbid. (gentle piano music) - This is morbid. - What's up, Big Red? - I'm exhausted. - Period. - We had a late over at our house last night where the kids got to stay late. - Those are all the rage these days. - They are, 'cause sleepovers are the worst. - Yeah. - But it's still the same, because everybody's exhausted. - Yeah. - And miserable, like really grumpy and not feeling well now, 'cause they didn't get enough sleep. - I used to be the worst after a sleepover. - Yeah. - I would be like, "I don't feel good, shut up. Don't talk to me." - Yeah, that's essentially what's happening right now. - Yeah, that's brutal. - So that's what I'll return to after we record. - I slept last night, but my body didn't get the message that it was sleeping, I think. - That it happens to look up and I was like, "Did I sleep? Did I though?" - Hello. - And today I kind of just feel like I'm not here. - Yeah, I'm not. My aura ring keeps telling me I have minor signs of strain. - I just stop wearing mine because I was getting too invested. - 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 it, I'm not good at telling myself to slow down. - Yeah. - Normally, but when I see it like that, I'm like, "You should really slow down." - 'Cause you know that you're affecting your body. - 'Cause I can see my heart rate. I can see my sleep. I can see what it's affecting. So I think it's helping me be like, "Hey, you gotta chill out." 'Cause I have manifesting. - I have such an addictive personality that I'll just go way too far in the way and change my whole life in a ridiculous way. - Yeah, I'm just looking at it. It's like, "Hey, maybe don't have ice cream late at night." And get more sleep. (laughs) - That's not the way to live though. - No, I've had, it's working for me. - Ice cream at night is the best. - Oh, I love it at night, but only, but I was eating it way too late. - Oh, okay. - And then you're digesting all night. - What's too late? And they say you should like one or two hours before you go into sleep for like two hours before you go into sleep. - I made slutty brownies the other night. I love slutty brownies. - 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 nine p.m. - That sounds delicious. - And then I went to probably at like 10. And yeah, I had the worst heartburn of my life. There you go. - Absolutely. - A lot of fucking chocolate. - So they go. - To just directly lay down. - And then you just lay down. - It turned over to your room, like heartburn. - And he's like, "Yeah, I can't imagine from what." - Yeah. - It's crazy. - It's like, "That's so nuts." - Yeah, and just be like that, you know? - And here's the thing. I like to live my life that way. - So, if I don't, yeah. - It is what it do be. Yeah, I just like, I like having the control of everything. - Yeah. - 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. - A series. - That we kind of dip into every once in a while. - Okay. - We talked about doing notorious prism breaks. - Yeah. - So I have two today that we're gonna talk about. And then we'll talk about a couple more in a couple weeks. - Okay. - You know, we'll sprinkle them in. - Yeah. - You know, they're a fun little detour. - It's always fascinating when people break out of prism. - Because it's, there's true crime here. - Yeah. - There's, there's fascinating prism life. - You're fascinating prism life. - Yeah. - And then there's somebody escaping from fascinating prism life. - Sounds like a TLC show. - Fascinating prism life. - I like that. - Have I got up on fascinating prism life? - No, I'm not caught up on it yet. - Well, no. - I don't know if I can return it stresses me out. - So today? - Yeah. (laughing) - I don't know if I can go back. - I don't know if I can go back. (laughing) - I'm also like fully in like draft writing. - Oh, yeah. - So my brain is a wasteland right now. - Yeah. - Your brain, I would like to look at it. It's just got a lot of weird shit in it right now. A lot of weird research happening. - Yeah. - Let me cough. The way you said that was so aggressive. You were like, let me cough. Like I wouldn't let you. - I really had to cough, but I was like, I have to do it now, so I was like. - Let me cough. - I wouldn't feel like let me cough. I don't say anything, but shut up. - I had to let me cough. - You leave that in, take the cough out, but you leave that little back and forth in. So let's talk about John Dillinger and his escape from crumb point. I feel like I know him. You should. - Yeah. - He's pretty infamous, I would say. So we're gonna go back to the Dust Bowl. - Oh fuck, it's going to the Dust Bowl. - 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. - Okay, soos, so (laughs) - Okay, poet. - That's Dr. Soos, don't forget about my MD. - Oh yes, of course. - So yeah, I'm sure you've heard of John Dillinger. - Yeah, I also think, I learned, I like definitely learned about him, but I think we talked about him briefly on crime countdown. - 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. - Oh, okay, he was just being an asshole. - In the crime, you know? He was arrested a few times for minor thefts, just getting drunk, getting in fights. After he was arrested for stealing a car in 1922, you know, those were in 20s. - Oh, can't stop him. - He meant you can actually, like the great oppressions gonna stop him. - Yeah, it's up to them. - It's up to them, they're trucks to be afraid. - He managed to avoid serious consequences by enlisting in the military. - Ah, there it is. - And he served two years before being dishonorably discharged in 1924 and returning home to Indiana, where he married his girlfriend, Barrel Joveus. - Barrel, isn't that? - Barrel Kiff's mom's name. - Kiff's mom's name. - Shit. - And I never thought I knew another Barrel. - Here you do. - Here you do. - Check that out. 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, due to post-war overproduction and declining prices. - Shit. - 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. - Yeah. - Like little towns in Indiana. And Dillinger was kind of struggling to find stable work at this time. So he's frustrated. He's like, this is annoying. He's gonna crime again. - He's out of options. Sometimes he just got a crime, I guess. He's out of options. So he and his friend Ed Singleton, you know, they just robbed a local grocery store. - I knew he was gonna crime again. - He crime 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. - Damn. - But Singleton served just two years before being released. - Okay. - Now at first, John and Barrell kept in touch through letters and she would visit whenever she could. - Romance. - But the distance, you know, the prison distance, it's in the long term separation where a little too much for Barrell. - They didn't get life after lock up. - Yeah, they did not get that. And in June, 1929, just two days before his birthday, she requested it was granted a divorce. - Barrell. - She said, "I don't want to have to get you a birthday gift." - Oh, damn. - She said times as tough. - She did. - She said, "Happy birthday. We're divorced." - And he's in prison, so she's like, "And are you fine?" - But 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 that eventually made him quote, "Public enemy number one." - Men love to blame women for everything. - 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." - It's probably that. - I feel like that feels more like the fault here. - No, that was her fault too. - Definitely her fault. - Everything is Barrell's fault. So during his time in prison, he associated with several other known criminals, as one does. - Yeah. - Including bank robbers, Harry Pierpont, Russell Clark, and Charles McLean. To pass the time, they would just recount their stories of their successful heights. You know, they were kind of like those guys who talk about being quarterbacks in high school football. - Yeah. - Well, they're like, "Where's the time when we robbed a bank?" And you're like, "Yeah, I do because you're in prison." - Yeah. - And they would plan future robberies that they hoped to carry out once they were released. They were dreaming big, you know? - That's good to do in prison. - We're in prison now, but like, let's keep crime in one round. - Yeah, perfect. - Although he had been sent to prison for robbery, Dillinger's crime was nothing compared to the crimes of Pierpont Clark and McLean. And it was through them that he learned the ins and outs of criminality that he would later use for his later crime spree. - Done, done, done. - After serving nearly 10 years in prison, - Demon is served to the grocery store robbery, he was released in May 1933 at the peak of the Great Depression. - What a time to be released. - Yeah. - 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. - Oh, yeah, it's never your own fault. - He robbed a grocery store. - Never ever look within. - No, never, no. - Never some introspection to me. - Who does that? - Don't do that. Having been released at, you know, arguably one of the worst periods in America this year. - Have you seen today? the economy was concerned at least. John Dillinger didn't bother investing much time and finding a job that he knew was not out there to be found, which like that. He's not wrong and not there won't try. Instead, he found he put his newly developed criminal skills to work. And in late June, just one month after being out of prison, he robbed a bank in New Carlyle, Ohio, getting away with $10,000. Dang. Ten times the average annual income for an employed American at the time. Holy shit. Yeah. Dillinger's success led him to begin immediately planning his next heist. This time, though, he was captured by police in Dayton, Ohio in thrown in jail. Well, it's like, did you even need to do another heist at that point? You got to wait with 10K, baby. It's like a gambler. Yeah. Like they get that high and I'm not like I can do this again. Police seem confident that the arrest put an end to his criminal career. But what they didn't know is 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, convinced several former prisoners to smuggle guns into the cells of Pierpont, Macle and Clark, the three guys that he was back in jail with. Okay. And several other prisoners, which they used to escape from prison. Damn. How do you smuggle guns into a prison? So the gang kept a low profile for a few weeks before setting the second phase of the plan into motion on August 12, 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. Okay. Even though there was like no paperwork to say who's being extradited, iconic. Now, unfortunately, when they conceived of the plan and never occurred to the members of the gang that someone might, you know, like you said, want to see identification, 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. He shot the sheriff. Damn. But he did not shoot the deputy. He did not. He just got JD. He did not. But now free from jail. Dillinger and his gang spent the next three months robbing banks all over the Midwest. They got them out. They busted them loose. At a time when organized crime was on the rise in America and career criminals like, oh, I don't know, Al Capone, her lucky Luciano, your guy. They were becoming folk heroes at this point. Yeah. Dillinger and his gang immediately caught the attention of the press and became household names. Their pictures plastered on the front pages and 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. You don't want to be notorious with your face in the papers when you're robbing banks. While you're crime. In late January 1934, two firefighters in Tucson, Arizona recognized the group when they were escorting guests out of a hotel during a small fire. Dang. 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. Hey, I know you. 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. Wow. So they were like kind of dumb. 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. Yeah, I'd say. But it didn't work out that way. Okay. Not at all. As soon as the door was opened, Russell Clarke assumed the man at the door was a police officer and rushed at him. Good. Just right away. Good. While a woman in the house quickly slammed the door before the other officers could even get inside. Shit. And when she slammed the door, she crushed one of the officer's fingers in the process. Inside Clarke in the undercover officer, Chet Sherman fought over Sherman's gun, wrestling one another all over the living room in a Joyce Jason bedroom. Clarke finally managed to draw his own gun and pointed at Sherman, the police officer. But by then, the other officers had made their way inside and subdued Clarke. Later that day, police arrested Dillinger, Pierpont, and Mackley or Markley, but or known as Mackley. Sorry. I thought I was being very too Boston. But the rest of the gang managed to get away. Oh, wow. Now in a statement following the arrest, the commissioner of public safety, Al Fini. Fina. Fina. There it is. Told reporters, it is a great relief to the state to have these desparados and 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 desparados. I'm like, most people do quit when they don't. And I love that he was like, don't know bitches. That is kind of funny. Essentially when he said, "Fuck him." 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. Yes, so they did not need to keep doing this. No, they were gluttonous. Just fucking cut that money and run. Gluttony. Now on the trip back to Indiana, Dillinger spoke freely with their detective escorts. He told them before freely confessing to the robberies. There's no use denying anything now. I mean, you are caught red-handed. To the officers in the escort party, he's appeared to be in fear of spending the rest of his life in jail. So he confessed in the hope of leniency. Now, one of the detectives told the 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. And what the detectives recognized as defeat in desperation was, in fact, privado in a lot of confidence. All four members of the Dillinger gang were placed in separate cells in the Lake County Jail and Crown Point, Indiana, where they were waiting 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. Yeah. Since his incarceration, the local police had touted the jail as, quote, "escape proof." Oh, that's like calling the Titanic unthinkable. The unsinkable ship. But on March 3rd, John Dillinger proved them wrong. Had a feeling. That morning, Deputy Sam Cahoon, great. I know, arrived in the cell, Dillinger shared with another inmate, Herbert Youngblood. Herbert Youngblood. His 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 helped by Dillinger, who instructed him to unlock the door. Have you looked up a picture of John Dillinger? I don't think I have. He's exactly what you think. Show me this man. Oh, oh, yeah, I've seen that. That's, I've seen that picture. Yeah. Honestly, good for him. Yeah. Good for him having that kind of smirk. He's really killing it. I'm kidding. Everybody. I know he's a bad guy. Yeah. This kid just got to make sure. Oh, so it looks like he has spider webs on his, on his tie. Maybe he does. So this looks like spider webs. It does, actually. He's got a very cleft chin. Yeah, he got a booty chin. No, and I can say that because I have a booty chin. 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 to them in his former cell. Oh, my God. Then he nodded to Cahoon, indicating that he was to be a sausage. He was like, come with me. Oh, no. From there, Dillinger went through the jailhouse slowly rounding up all the deputies in the warden taking their guns before locking them in the cells and the warden, a fuck, inescapable. This is jail. Before leaving the jail, Dillinger grabbed two silver submachine guns from the warden's office. Oh, my God. Once they're outside, he located the nicest car in town, a brand new Ford F8 or V8 that belonged to none other than Sheriff Lillian Holly and took it and drove off towards Chicago. Wow. So he escaped the inescapable jail. Yeah. Took two silver submachine guns from the warden and then stole the sheriff's brand new car. I mean, you got to do that little finger thing. I'm like, I know it's wrong, but like that's not encouraging. It's just hearing it now. So many years later, don't do that. Now the news of Dillinger's escape came as a shock to some and a delight to others, especially those who'd come to see the man as kind of a depression or a hero. I mean, but to Lillian Holly, the sheriff and the deputies at the jail, it was a national embarrassment. Yeah, I'd say so. Holly had colorful things to say. He said, if I ever see John Dillinger, I'll shoot him through the head with my own pistol. Do you still have your pistol? He said, did he take it though? Is it in your car? He shoots you with your own pistol. Of course, the question on everyone's mind was, how had he managed to escape from a supposedly escape proof prison or jail? There is 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 Piquet. With his trial scheduled from 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. Okay. A few days before the prison break, Pequette paid a visit to his client where it's believed he either slipped to me wooden gun, or he gave him the tools to whittle it himself. Yes, you heard that right. It was a fake gun. One Dillinger had carved the gun or received it. He painted it black with shoe polish. Stop. And no one could tell the difference. Stop it right now. 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. Okay. Either way, once he forced the deputy to open the cell, he took the man's weapon. It was legitimately armed at that point, but this could have started with a wooden gun. That's insane. Yeah. Now with Dillinger on the run, the sheriff formed a massive posse and began the hunt for the escape criminal who had by then already traveled across the state line into Illinois and onto Chicago. I love to think I love to think of the sheriff just like running deep with his posse. Right. Just deep. It's formed a posse. Deep with his posse cat dolls. Well, and on the way to Chicago, he picked up his girlfriend, Billy Forchette. Dillinger did. Okay. 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 Forchette, 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 Equentance Lester Gillis, better known as Babyface Nelson. Oh my God. In the three months that followed, Dillinger and the new gang robbed several more banks across South Dakota and other parts of the Midwest. It is remarkable that they still were able to pull off these robberies. Like it's not good, but I'm just like holy shit. Pretty remarkable. Dillinger's reign finally came to an end on July 22nd, 1934, when Federal agents tracked to Chicago's biogram, tracked him to Chicago's biograph theater and a shootout and suit. In the firefight, Dillinger was shot four times with the fatal bullet entering the back of his neck and traveling into his brain before exiting just under his right eye. I mean, how do you think that's going to end? Yeah. I think criminals like him just live so fast. Oh yeah, they just know that it's going to end in a blaze. And I don't even think they like think of it. Well, I think they just don't care. They're going to, they're here for a good time, not a long time. Yeah. Is there truly a mono? I really think that. And I think they think that they'll have a lot of smart. They do. Yeah, they always think they're smarter. That's an insane story. No, 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. Yep. 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. Okay. Established in 1859 as a military prison alcatrazal penitentiary was transitioned to a civil civilian federal prison prison. Goddamn. In 1933. Yeah, I think I've heard of it. And it was almost immediately America's most notorious prisons. Yeah. It has some of the nation's most infamous criminals, including Al Capone. Yep. George machine gun Kelly Barnes. My distant relatives. Yep. An Alvin creepy carpis carpivitz. Yep. Situated on an island about a mile and a half from the shore in San Francisco. Alcatraz was 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. That's crazy. And also in the highly unlikely event that the prisoner somehow managed to get through the walls and walls and then pass the guards and over the razor wire fences, San Francisco Bay still presented a pretty insurmountable problem. It's going to say you are surrounded by water. Not only is the water freezing cold and prone to strong, fast currents, but the area is also home to several species of sharks, making it almost impossible for someone to successfully swim across. Which is so interesting because sharks usually like warm water, no, okay? I guess so. I don't know. I don't know if they're different, like different species, yeah. Now despite the odds being very much against a successful jailbreak, and it's 29 years as a federal prison, 36 prisoners attempted to escape on 14 different occasions. 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 the re-escapies not only made it to the water, but were able to get away from the prison and remain unaccounted to for to this day. That's insane to me. This one's crazy. So born and raised in Georgia, John and Clarence, England had a pretty difficult childhood. As two of 13 children, one of the 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. A petty crime. And within a few years, they graduated to bank robbery. Big crime. Bigger crime. And in January 1958, they were arrested and sentenced to 35 years at Leavenworth penitentiary. Fuck. From the moment they arrived at Leavenworth, the England brothers began scheming away 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. And that is how I would like to escape from prison. I was a little friend to 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 and said, Hey, you're not red. 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 he said, fuck y'all Alcatraz. You go on Alcatraz. It was at the prison that John and Clarence met their future co-conspirator, Frank Morris. Like the England brothers, Morris had been a criminal for pretty much all of his life or fined at age 11 when his mother handed him over to the foster system. Morris spent seven 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. In April 1955, Morris was serving a 10-year sentence at the Louisiana State Penitentiary, which is also not to be ignored. Not to be fucked with. For robbery when he and another inmate managed to escape that prison. The two 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 Lydell. Then they fled the state for Kansas City and 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. That will do it. Serving time in the Missouri prison before being sent to Alcatraz in January 1960. Okay. 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. I mean, you would have to plan that forever to be successful. A few weeks after arriving in Alcatraz in January 1960, Frank Morris was moved to B-block and placed in a cell next to Alan 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 you 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. After orchestrating a small riot during which one of the other prisoners was stabbed. Oh, fuck. 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. Yeah. Now over the course of six months, the four 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. I fear we can't move past the fact that as prisoners, they had access to saw blades. Old saw blades. Old saw blades. Where'd you guys get those? Yeah. Hello. No, what's funny about this is you're probably, didn't anyone hear them digging through a wall? You would think, especially a saw, West would play the accordion to cover the nose and the noise of digging. I con it. Yeah. I don't know. I would think that in prison, that would be the last thing that you would have as an accordion. I don't know. I mean, I've never - I've never been. - I've never been. I don't know if they maybe they hand you one when you come and do something, but 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. They had access to so many material. They were illusionists. They were mind-freex. They were mind-freex as well. After several months of digging, they'd widen the hole enough so they could get through into the shaft. And 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 in life preservers out of dozens of raincoats and other waterproof items they'd managed to collect over the course of six months. This is like a weird, like, eye-spy collection. 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 four men could have tunneled out of their cells night after night, and their absence wouldn't have been noticed by the guards. You're probably like, no. Maybe they were whole nights with the guards. They were going up every night. No way. Nobody's homeies with the guards at Alcatraz. No. It was only later after they escaped that prison officials realized the men had used plaster heads made life-like with painted faces and hair contrived from the bristles of paintbrushes to disguise their absence. I remember this. This straight-up, like, made little mannequins of themselves. They were crafters, crafters at heart, crafters at heart, and another time, given somebody sitting them down and being like, let me really tell you what you're good at, they could have had Etsy shops. But they would kill at flea market flip. They would. Wow. A farmer's market? Get out of here. Maris Spencer would love them. Yeah. But no. They had to do this. Paint from the maintenance department and discarded hair from the barber shop. They each constructed the base from paper mache, they're using paper mache, and design them in each of their likenesses, like, so they both had a special project of, like, making their own license. Rafty kings. In the dark, when the blankets pulled up tight around the necks of the dummies and the head 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 was sleeping. Oh, my God. Yeah. But they, like, low-key deserved this issue. They kind of did. I'm going to go on record. I'm not saying they're good guys, but they kind of, they did their big one, wasn't it? They really worked for. I'm like, damn, just, like, go into the art. Use it for good. Go into the art. No. On the evening of June 11, 1962, just after lights out, it was called at 9.30 p.m., the men put their plan into motion. Here he is. Once the guards were out of sight, Frank Morris and the Anglin brothers piled clothing and towels under the blanket and placed the paper mache head on the pillow. Also, like, do we not do cell checks back then? 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. No. No. Now, unaware that Alan West was stuck in his cell and not wanting to waste any time, the three men climbed up the drain pipe, 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 the block. Then they shimmied down of kitchen vent that led to the prison yard. Under the cover of darkness and carrying their makeshift raft, the three men somehow managed to make it across the yard and over two large fences topped with razor wire. Or they reached the northeast edge of the island. This is bongers. Using a concertina borrowed by another inmate, which they'd fashioned into a kind of makeshift pump, the three men inflated their raft, dawned their homemade life jackets, and set off from Alcatraz Island. And they left their homey. They left their homey. By the time Alan 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 three were long gone. Oh, that's so sad. There's no, why do I feel so bad for this criminal here? 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 seat. He said, "You know what, prison is all right." He said, "I'll just stay here." Damn. And 15 a.m. a guard dog, do it, er, a real guard. I don't know why. A guard dog. 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. He was like, "Fuck, this guy's real sick." The guard stuck his hand through the bar and touched the head that lay on the pillow in his heart's sunk when he realized it was nothing more than paper mache. Pulling his hand back quickly, the head rolled off the bed and landed on the floor. Stop it. A piece of the nose breaking off in the process. Stop it. 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 prime time spot on the cover of the New York Times. I mean, I would think. It was not as the no one had ever heard, er, or had ever attempted to escape the escape proof. I was done 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, wore it in all in black, well, all in black, well, exasperatively replied, "I don't know. I just don't know." I was like, "You know what, fuck him." He was, he's me this morning. He was like, "I don't know. 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." He's like, "I don't give a shit." He's like, "I don't know. Did you see their fucking problems?" Yeah, who fucking knows? Yeah, who fucking knows. A few hours later, and then 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." Fuck. Like, you don't say. I think, thanks, Warden. Details in the escape were quickly ascertained when Blackwell and the investigators questioned Alan West, who claimed the plan had been devised by Frank Morris. He was like, "I don't do it." Just 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 three men would have struggled considerably to navigate their way to shore. Okay. 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. Huh. In the days that followed, countless tips were called in from citizens who, of course, believe they had seen Morris and Anglin, but not amounted to anything more than really mistaken identity. In the meantime, questions began to roll in as how three prisoners had managed to execute this crazy elaborate plan and escape, again, escape proof alcatraz. 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 decades, exposure to the elements and the saltwater because it's on an island had weakened much of its infrastructure. That makes a lot of sense. Blackwell said, "I would say erosion made the escape easier. How much easier?" I don't know. Again, I don't know. Who knows? He just doesn't know. The authorities searched for the three escapees for months, but aside from one of the ores and a makeshift life preserver found floating in the bay, which does tell me something. Yeah. There's not 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. Which we think they died. I don't know. The Marshall Service spokesman Dave Brannum said, "Although we never found the bodies, we presume they've drowned, but we think there is a possibility they're alive." Okay. So they're kind of like, "It could go either way." Yeah. I mean, those are the two possible outcomes. Yeah. They either died or they lived. Yeah. It's crazy. So they're not in purgatory. Okay, got it. They're not in a state of like a rusted development. No. He's like, "They actually got trapped in a parallel universe." It's like this isn't a twilight zone out episode, but that was in 1993. And apparently, like according to the FBI website, there was a plan they thought where they were going to like rent a car or steal a car. Okay. Once they got off the island. Yeah. That's how they were going to escape. Yeah. Yeah. I'm like, "You know what? That's easier." I'm like, "You know what? I'm just going to do that." There's a picture of the like plaster. The paper machine heads. It's crazy. When I tell you that, you know what? There's a picture of the like plaster, the paper machine heads. It's crazy. When I tell you, they were artists. Like I'm saying, couldn't be me. I couldn't have made that good of a plaster head. I don't think so. I'm also just like, "You guys could have found careers." -And those straight up hair, like they collected from the barbershop. And also, if you've ever watched sci-fi's face off, you know how hard it is to lay hair on a, like, makeup. -Yeah. -They laid hair. -That looked real. -Good for them. I was impressed by that. -They were determined for the cause. -They were. But I kind of hope they lived. -It would be. -I don't think they did, but. -I know. I don't know. But damn, it would be crazy if they did. I mean, you never know, crazier things have happened. -Well, the investigations into the escape exposed the considerable administrative and structural problems at Alcobre Tres, all of which would have required considerable money to fix. -Yeah. -And on March 21, 1963, the prison was closed for good. -Dang. -In the years since, it's become a national public park in a popular tourist destination. -It's supposedly haunted. -Oh, it is. -As for Frank Morris and John and Clarence Anglin, they were never seen or heard from again. -Crazy. -The Anglin's sister, May Widner, said in 2012, "I've always believed they made it, and I haven't changed my mind about that." -Oh. -And she isn't alone. -When asked whether he believed the prison escape was successful, U.S. Marshall, Michael Dyke replied, "We have to operate under the assumption they made it." -I mean, hey, that's a U.S. Marshall. -And they're saying, like. -Yeah. -That's what they're saying. -I mean, they didn't find their bodies, but they got off the island. -Also, sharks. That's the thing, you know? -Yeah, like, logic tells me they didn't. 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 sitting here being like. -But you know why? -Maybe they made it. And I'm like, "Oh, I guess if they did make it, they didn't really cause a stir after that." -That's the thing. They rehabilitated. And here's what I think happened. They opened up a studio altogether, and they taught pottery and paper mache and fucking art. -If you're in the San Francisco. If you're in that area, and you took art classes around this time. -It's an artsy area. -You had your life transformed by your art teacher. -Looked back. -That art teacher was one of these guys. -It was. They became art teachers. -And that's a fact. -So. -So doing that way, you will. -So you're welcome. -So put that in your pipe and smoke it. -It's true. -I'm obsessed. -I think they were mostly just like bank robbers, right? -I think so. -I think I'm not telling you about banks. -I think their bank robberies included moita guns and moita sometimes. -Well, I don't condone that. -But then they made crafts. -Crafts. -And they were your art teacher. -They changed your life. -I've never done paper mache. -I've never done it. -I saw this group of mache on TikTok, and she made the coolest paper mache pumpkin head. -Hell, yeah. -I'm going to find it and send it to you later. -I want to do that. -And I'll shout her out once they find her. But I'll never find her. I'm on TikTok far too frequently. -I'll never find her right now. -If it's you, let us know. -Did you make a really cool pumpkin head out of paper? -It was vintage. -It was vintage. Somebody tagged me in it so that I can shout them out. -Do it. -Plays. -Do the work. -Do the work for me. -So I don't have to. -No, if I tried to pull up a TikTok from. -Yeah. -It could be me. -It's bad. I have a scrolling problem. I probably am going to get carpal tunnel. -Anyway, we hope you keep listening. -We hope you keep it weird. -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. -Yeah. Bye. -They were your art teacher. [Music] [Music] [Music] [Music]

Podcast Summary

Key Points:

  1. John Dillinger escaped from prison in 1933 by using a fake wooden gun to deceive a deputy, highlighting the vulnerability of even supposedly secure institutions.
  2. After escaping, Dillinger and his gang robbed banks across the Midwest, drawing media attention that ultimately harmed their operations.
  3. The Alcatraz escape of 1962, involving Frank Morris and the Anglin brothers, defied all odds through meticulous planning, including digging through walls and creating realistic paper-mache dummies to conceal their absence.
  4. The escapees used creative materials like raincoats and hair from barbershops to build a raft and disguise themselves, demonstrating extraordinary ingenuity and craftsmanship.
  5. Despite searches and no physical evidence found, authorities and some officials believe the men escaped successfully and may still be alive, adding a layer of mystery and myth to the story.
  6. The failures of Alcatraz and Dillinger’s prison breaks expose systemic flaws in security and infrastructure, especially in aging, isolated institutions.
  7. Both escape narratives reflect a transformation from criminality to artistry, with the Anglin brothers reportedly becoming art teachers and influencing lives through creativity.
  8. These stories blend crime, resilience, and human creativity, illustrating how prisoners used ingenuity to challenge reality and redefine their identities.

Summary:

The transcript explores two legendary prison escapes: John Dillinger’s breakout from a mid-1930s Indiana jail and the 1962 escape of Frank Morris and the Anglin brothers from Alcatraz. Dillinger used a fake wooden gun to overpower a deputy, escaping after a short prison term and launching a criminal spree across the Midwest, only to be captured and later killed. His escape underscores the fragility of perceived security.

Meanwhile, the Anglin brothers and Morris, inmates at Alcatraz, meticulously planned a complex escape over months, tunneling through a prison wall and creating convincing paper-mache dummy heads to hide their absence. They reached the island’s edge and fled by raft, only to vanish without a trace. Though authorities declared them lost, some officials and family members believe they survived.

The story highlights not just criminal daring but also profound creativity—transforming from bank robbers into artisans and art teachers. These narratives reflect on the resilience of the human spirit, the limits of institutional control, and the enduring mystery of what happens when people break free. The accounts emphasize how ingenuity, artistry, and the will to survive can rewrite not just lives, but legends.

FAQs

John Dillinger escaped from Crown Point, Indiana jail in 1934 by using a fake wooden gun to threaten a deputy into opening his cell. He then used the opportunity to take control of the situation, stole two submachine guns, and escaped with his girlfriend, later driving to Chicago in a stolen car.

The fake wooden gun, possibly carved or painted to look like a real one, was used to intimidate a deputy into unlocking the cell door. This allowed Dillinger to gain access and initiate his escape from the prison.

Yes, in 1962, three prisoners—Frank Morris and John and Clarence Anglin—successfully escaped from Alcatraz by tunneling through a wall, using a ventilation shaft, and fleeing via a raft across the bay to avoid detection.

They created detailed paper mache dummy heads using paint and hair from the barber shop, which they placed on pillows to mimic a sleeping inmate. Guards could not detect the absence of real people, allowing the escape to go unnoticed.

The three escapees were never seen again. While authorities believe they drowned, some believe they survived and lived in hiding, and their disappearance has become one of the most enduring mysteries in American prison history.

Alcatraz was considered escape-proof due to its remote island location, strong guards, razor wire fences, and the difficulty of swimming across San Francisco Bay, which is cold and has dangerous currents and sharks.

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