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Tracy V. Wilson
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Holly Frey
Videos, but now the Old Gays are.
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Pulling back the curtain with their new podcast Silver Linings with the Old Gays, brought to you in partnership with iHeart's Ruby Studio and Vive Healthcare. Hosts Robert, Mick, Bill and Jesse serve their lifetime of wisdom when it comes to love, sex, community and whatever else they've got on the gay agenda. So check out Silver Linings with the Old gays on the iHeartRadio app or wherever you get your podcasts.
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Tracy V. Wilson
Happy Saturday. A Prison Break was part of our episode on William J. Sharkey earlier this week, and we talked about some more prison breaks in our Friday behind the Scenes. So today's classic episode is a set of six prison breaks, including one that we just mentioned in that discussion, and.
Holly Frey
This originally came out on May 11, 2022.
Podcast Promoter
Enjoy.
Holly Frey
Welcome to Stuff youf Missed in History Class, a production of iHeartRadio.
Tracy V. Wilson
Hello and welcome to the podcast. I'm Tracy V. Wilson and I'm Holly Fry. A few years ago, I was in Philadelphia and went to the Eastern State Penitentiary, which was a prison for about 150 years. And now it's a historic site. And one of the things I learned about while I was there was a dramatic escape from the prison in 1945. And I immediately put that into my little notes app on my phone where I jot things down when I'm on vacation. It was one of those things, though, that I couldn't quite figure out how to make it work as an episode, and I kept circling back to it periodically. It finally dawned on me that it might work as a set of six impossible episodes, because there are some common themes among a lot of the prison break stories, like there's often a lot of tunneling. So a couple times a year, I pull together six episodes that are grouped together in some way. And so now we're gonna have six prison breaks. And just to level set here, I would not at all call this a representative sample of history's prison escape attempts, because, number one, the vast majority of information we have for this episode is from places where English is the predominant language, and that's just a matter of what's available to us. Number two, I was really focused on escapes that seemed particularly ingenious and how they were planned and carried out, not on ones that were violent. So there is a little violence in this episode, but it is not one where the, you know, a prison break happened in the middle of a violent uprising where a lot of people got killed. I was really looking at the ones that are kind of offbeat a little bit in some ways.
Podcast Promoter
Right.
Holly Frey
This is more Shawshank redemption than horrible riot situation.
Tracy V. Wilson
Yeah, Several of them seem like clear inspirations for some of the Shawshank escape. So just know that going in.
Holly Frey
All right, so we're going to start with the prison break that inspired this episode. The Eastern State penitentiary opened in 1829, and it was built in an era when reformers were trying to change the way prisons and the criminal justice system worked in Philadelphia. This effort was led by the Philadelphia Society for Alleviating the Miseries of Public Prisons, whose members were predominantly Quakers. The prison was called a penitentiary because its purpose was to inspire penitence among the people housed there by keeping them in a state of isolated, silent contemplation. Hundreds of prisons that followed this theory were built around the world in the 19th century.
Tracy V. Wilson
Although these reformers were trying to move away from things like public floggings and executions for relatively minor crimes, and also to make incarceration more humane. This system that they devised was innately cruel. It came to be known as the Pennsylvania system. And it was basically perpetual solitary confinement. People were totally alone in these single occupancy cells that had attached small, walled in exercise yards. They were forced to wear hoods when they were in common areas so they couldn't see or talk to anybody else.
Holly Frey
And over time, the prison moved away from this practice and the Pennsylvania system was officially abandoned. By that point, more people had recognized that endless solitary confinement was in fact, cruel. But the system that replaced it was cruel just in a different way. Overcrowding became a major issue with new cell blocks built between the existing ones. Until a prison that had originally housed 250 people instead housed 1700. A series of riots and uprisings took place in the 1930s in response to poor conditions at the prison and. And to low pay at the on site workshops and factories where they were forced to work.
Tracy V. Wilson
In 1944, a plasterer and stonemason named Clarence Kleindenst, who was known as Kleiny, was housed in cell 68 of cell block 7. And this was at the far end of one of those cell blocks that had been planned as part of the prison's initial design as a penitentiary. And it's possible that he moved into the cell with the intention of tunneling out of it. From the beginning, it had been used for storage and. And he had offered to repair it so that he could live in it.
Holly Frey
Once he was housed in cell 68, he and his cellmate, William Russell, started digging a tunnel in secret. One that went through the cell wall, then down 12ft, requiring a ladder to get to the bottom. From there, the tunnel leveled out and stretched about 100ft, running under the exercise yard and the wall that encircled the prison, and then up again to the street outside. They made a plaster mask so it would look like one of them was in bed, that one would dig while the other kept watch. And they'd put the dirt they dug up in their pockets and then scatter it in the exercise yard.
Tracy V. Wilson
Kleindenst hid the entrance to this tunnel with a panel that he made to roughly match the intact walls of the cell. And then put a metal trash can in front of it and in the tunnel. He shored it up with wood and installed lights and ventilation fans. When the tunnel intersected with a sewer pipe under the prison, they built a connection to the pipe so they could dispose of their waste through a sewer. This was a complex engineering feat handled with whatever they could cobble together.
Holly Frey
It's pretty ingenious. On April 3, 1945, 12 men escaped through this tunnel going to cell 68 while everyone else was on the way to breakfast. At the end of the tunnel, they broke through the last few feet of earth and scattered in different directions as they came out of it.
Tracy V. Wilson
Most of them though, were back in the prison within a day and all of them had been caught within a few months. Notorious bank robber Willie Sutton, who would later totally take credit for this escape in his autobiography, he was caught almost immediately. He basically came out of the hole and they grabbed, grabbed him right there. Clarence Kleindenst was in custody after about three hours. One group tried to make their getaway in a milk truck that they stole and they were caught after police rammed the truck with a police car. One man, who was 24 year old, James Grace, turned himself in eight days after the escape. William Russell and one other man were both shot during the escape attempt and they were brought back to the prison infirmary. Otherwise, the men who tried to escape were punished. Some of them were placed into these tiny windowless underground cells known as Klondikes. These were too small to even stand up in.
Holly Frey
Of course, this whole escape was enormously embarrassing for the prison. It was not at all the first escape attempt or even the first successful escape attempt from the Eastern State Penitentiary that had happened all the way back in 1832. But it was a colossal security breach. Months of digging had gone unnoticed and more than one inspection of cell 68 had failed to spot that tunnel entrance.
Tracy V. Wilson
Prison authorities investigated and mapped the tunnel and then they filled it in and covered up the entrance with cement. Then later in 2005, Eastern State Penitentiary embarked on an archaeological study to find and map the tunnel. This effort included ground penetrating radar work, cameras and a small robotic rover that was kind of remote controlled and went down the tunnel. They had to use a jackhammer to get through. The tunnel's covered over entrance.
Holly Frey
As we said earlier, Eastern State Penitentiary is now a historic site. And as of 2017, its mission is to interpret the legacy of American criminal justice reform.
Tracy V. Wilson
Yeah, we'll talk about that a little bit more in the behind the scenes on Friday. Moving on. For about 80 years, starting in 1788, people convicted of crimes in the UK could be transported to Australia as punishment. Other colonies as well. But Australia is the focus here. Often this was for a period of seven years. But a lot of people sent to Australia never returned to Britain again. They either couldn't afford to make the trip or they didn't want to. After having made A life for themselves in Australia. Australia. And only a small number of people who were sentenced to transportation had been convicted of a violent crime. A lot of them had been convicted of offenses that most people would think of as pretty petty today. Women in particular tended to have been convicted of things like stealing handkerchiefs or cloth or pickpocketing.
Holly Frey
Our next prison break was a group of women who were being held at Limerick Jail in Ireland, awaiting transportation to Australia. They were supposed to be transferred to a prison in Cork on May 23, 1830, which is where they would embark on this ship that was going to take them to Australia.
Tracy V. Wilson
But the night before that transfer to Cork, nine women and a baby escaped from Limerick jail. The women were Mary King, Mary Hurley, Mary Devon, Ellen Hurley, Margaret Shaughnessy, Margaret Clancy, Bridget Shelton, Mary Hickey and Catherine Welsh. And the baby was Mary Devin's 11 month old daughter.
Holly Frey
As escapes go, this one is maybe less dramatic than some of the others that we're talking about today, but it does still involve some ingenuity. Leading up to their transfer date, these women made a habit of singing and quote, noisy vociferations after dark. So it had been established that they were just loud. Someone had provided them with a file, some nitric acid, also called aquafortis, and other tools to help them get out of their cells. Then on the 23rd, two men used a ladder that workers had left behind while making repairs to get into the women's ward.
Tracy V. Wilson
The men started helping the women get their cells open while the women got to their nightly singing to cover up the noise. In the words of the Monmouthshire Merlin quote, this amusement they enjoyed with more than ordinary spirit. On this occasion, and without exciting any particular notice, meantime, the iron fastenings were assailed by the burglars with extraordinary success. The continued knocking was heard in the adjacent ward, but the sound of their operations was so drowned in the melody of the accompanying voices as not to reach the ears of the jail governor or his assistants. The locks gave way before repeated efforts and nine females with an infant were extricated from durance vial.
Holly Frey
Once they were out of their cells, the women and their accomplices climbed back down the ladder and used it to get over the outer walls unnoticed. But these women did not stay at large for long. Mary Hickey was caught the night of the escape and newspapers reported on the capture of other women in the following days, including Catherine Welsh, who asked to be taken back to the Limerick jail after being caught shoplifting.
Tracy V. Wilson
Yeah, they were going to take her to a different jail and she was like, can I just go back to Limerick? Because that's where I escaped from. It appears that with one possible exception, all of the women involved in this prison break did wind up being transported to Australia. Two of them are mentioned in an article about a ship that departed for Australia on January 29th of 1831, and then all but one of the rest of them are listed on ships, actual registers of the people being transported. So there were five on a ship that departed on September 27, 1831, and then one on a ship that left on March 9th of 1833. So that leaves only one of the women unaccounted for.
Holly Frey
We are going to take a sponsor break and after that we'll come back to more escape stories.
Big Three Basketball Announcer
The reviews and ratings are in and Ice Cube's Big Three is the surprise hit of the summer. And to cap off the season, iHeart presents the Big 3 Basketball Championship and 8th Annual Big 3 All Star Game this coming Sunday, August 24th. Live from Orlando, the remaining Team 2 teams fight it out for the Big 3 Championship Dr. J Trophy in the most physical, fierce and competitive basketball league in the world. Don't miss the wild conclusion of Big Three's eighth and most historic season ever. This is the game no one wants to lose and there's no crying in the Big three. The action starts with the Big Three eighth Annual All Star Game. Don't miss All Stars Dwight Howard, Montrez Harrell, MVP Michael Beasley, Lance will make you, Dan Stephenson, Jordan Crawford, Greg Monroe, Earl Clark, Nazir Kor and more show you why they are the best three on three basketball players in the world. Big three's exciting all star game plus the crowning of a new big three champion. The no holds part action starts Sunday at 2pm Eastern, 11 Pacific only on CBS.
Holly Frey
Listen to your elders, honey.
Podcast Promoter
You might know them from their viral videos. But now the old gays pull back the curtain on their brand new podcast, Silver Linings with the Old Gays, brought to you in partnership with iHeart's Ruby Studio and Veeve Healthcare. With over 300 years of experience between them, hosts Robert, Mick, Bill and Jesse serve four lifetimes of wisdom when it comes to love, sex, community and whatever else they've got on the gay agenda. Listen in to these fabulous friends swap stories exploring how queer life has evolved over the decades and the silver linings they've collected along the way. Each episode dives into hot topics from safe sex and online dating to untangling Gen Z lingo, as well as insights on how music, art and fashion show up in queer culture, so check out Silver Linings, a show about how pride ages like fine wine.
Holly Frey
Available on the iHeartRadio app or wherever.
Podcast Promoter
You get your podcasts.
Ryan Seacrest
Hey, it's Ryan Seacrest for Albertsons and Safeway. Now through August 26th, it's back to Deals Time, where you can enjoy storewide deals and earn four times points. Look for in store tags to earn on eligible items from Kettle, Haagen, Dazs, M&M's Ritz, Chips Ahoy, Arrowhead, All Poppy, Charmin and Red Bull. Then clip the offer in the app for automatic event long savings. Shop in store or online for easy drive up and go. Pickup or delivery subject to availability restrictions apply. Visit Albertsons or Safeway.com for more details.
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Tracy V. Wilson
Next up, we have the Escape from Alcatraz. In 1962 and way back in 2008, prior hosts of the show, Candace and Josh did an episode titled Did Someone Really Escape from Alcatraz? Number one. That is forever ago. It was an entirely different show with a different format at that point, and Most of that 10 minute episode is focused more on the general history of Alcatraz as a prisoner and not on the escape itself. If you're interested in the more general history of Alcatraz, we talk about that a bit in our two parter on the occupation of Alcatraz. Those episodes came out in 2019.
Holly Frey
So Alcatraz is an island in San Francisco Bay. It has a steep, rocky shoreline and it is surrounded by treacherous waters. Although this may have discouraged people from trying to escape, there were still 14 different escape attempts during Alcatraz's time as a federal prison. That was from 1934 to 1963. Nearly all of the 36 men involved in these attempts were captured or killed, but five of them are classified as missing and presumed drowned. Two of them were Theodore Cole and Ralph Rowe, who filed through the bars of A window in the mat shop and tried to escape during a storm in 1937. The other three were involved in the 1962 escape.
Tracy V. Wilson
There were actually four men involved in this attempt. Frank Morris, John Anglin, John's brother Clarence, and Alan West. They had all been convicted of various burglaries, robberies and thefts. And they'd all been incarcerated together before, and they all knew each other. They had been transferred to Alcatraz after having tried to escape from other prisons. They started planning to escape from Alcatraz in December of 1961. Morrison. The Anglins had been assigned cells that were adjacent to one another, and one of them found some old saw blades they thought they could use.
Holly Frey
These men improvised so much for this escape attempt. They improvised tools to dig and break through walls, including making a drill from a vacuum cleaner motor, although that turned out to be too noisy for them to really use. Scrap wood became basic paddles. And a concertina that is a musical instrument that's sort of like an accordion, became a pump to inflate their raft.
Tracy V. Wilson
And that raft, apparently using instructions they found in Popular Mechanics, they made a 6 foot by 14 foot raft out of about 50 raincoats. They may have taken some of these raincoats from other men by force, but there was also a rumor that if anybody successfully escaped from Alcatraz, the government would shut the prison down. So it seems like some of the men were happy to kind of wear their raincoats out to the exercise yard and then leave them there to be picked up, kind of donating them to this effort to get the prison shut down. The escaping men then used contact cement they had stolen from various workshops around the prison and heat from the steam pipes to vulcanize the seams of the raft. And they used this same method to also make life preservers.
Holly Frey
Each of their cells had an air vent, and they used various tools to make a series of holes around these vents so that the whole thing in each cell could be pulled out from the wall. This got them into a utility corridor where they made and hid what they would need to escape. Yet another improvised tool with all this was a periscope, which they used to watch for guards while they were working. They also worked out a way to get from the corridor and onto the.
Tracy V. Wilson
Prison roof, similarly to how Clarence Kleindenst and William Russell had used a mask they made to make it look like one of them was in bed while the other one was digging a tunnel. These four men made heads out of homemade plaster and painted them, topped them with human Hair so that it would make it look like they were asleep in their beds. These heads, I think they're actually pretty good. They're better than I could do, I think.
Holly Frey
On June 11, 1962, Frank Morris and the Anglin brothers went out through their removed ventilation grates, covering the hole behind them with whatever they could. Allen west had tried to reinforce the concrete around his grate and had accidentally cemented it in place. And by the time he was able to get it free, his accomplices had already left.
Tracy V. Wilson
From up on the roof. Morris and the Englands climbed down a smokestack and then over a fence, cutting through the barbed wire at the top of the fence. And then they seem to have launched their raft from the northeast corner of the island. But then what happened to them after that is a mystery.
Holly Frey
During bed check on the morning of June 12, a guard at first thought that the three men were still asleep in their beds, but then realized they weren't in their cells. After touching one of the fake heads through the bars and a manhunt began. Authorities recovered a package of letters sealed in rubber paddles and life vests, either in the water or washed up at various points around the San Francisco Bay. Sailors from a Norwegian freighter reportedly saw a body in the water on July 17, but did not report that until October.
Tracy V. Wilson
Although there have been some simulations that suggest that the three men could have made it to shore was theoretically possible, at this point they are presumed to have drowned in their escape attempt. The FBI closed the case on December 31st of 1979.
Holly Frey
Although Alcatraz did close less than a year after this escape, it was because the prison needed a multi million dollar restoration project. And on top of that, it was expensive to operate because of its island location. The federal government decided that it would be cheaper to just build a whole new prison than to try to restore and keep running Alcatraz.
Tracy V. Wilson
Next up, Libby Prison was originally a food warehouse and then later it became home to a grocery and ship provisioning business. Was in Richmond, Virginia. And during the U.S. civil War, the Confederate government took it over and turned it into a prison to house U.S. u.S. Prisoners of war, particularly U.S. military officers.
Holly Frey
And conditions there were really just appalling. Obviously it was not built to be a prison. And beyond that it was situated on a canal that routinely flooded the building's cellar in wet weather. And the rising waters drove rats out of the cellar and into the rest of the structure. The windows were open spaces covered in bars and they let in little fresh air but not much light. They didn't offer much protection from storms or extreme temperatures. The upper two floors where the prisoners were housed were very sparsely furnished. There weren't even enough bunks for everyone. This was an immensely overcrowded facility with as many as 1,000 people packed into just six rooms. Without enough food or supplies, unsurprisingly, disease was rampant.
Tracy V. Wilson
Colonel Thomas E. Rose of the 77th Pennsylvania Volunteer infantry started planning an escape almost as soon as he arrived at Libby Prison. He thought it might be possible to dig a tunnel from that rat filled cellar to a nearby tobacco shed where they could get out without being seen by guards. Because all of the rats and the ongoing flooding problems made the cellar smell terrible so so bad that it was nicknamed Rat Hell. That also meant the Confederate guards mostly stayed out of it. So this was one place they could work on a tunnel, mostly undetected.
Holly Frey
Construction of an escape tunnel started with removing bricks from behind a stove in the kitchen, which was the only room the imprisoned men were allowed free access to. This made an entry into the cellar, and from there Rose and his accomplices started digging with makeshift tools, putting the dirt into an old spittoon to take it away. It was hard to tell how far they'd gotten, though, and at one point they broke through the surface and realized that they still had several feet left to go. They managed to fill that accidental opening in before they were noticed.
Tracy V. Wilson
Robert Knox Needen was a cartographer who was being held at a neighboring prison, and he wrote this account of the escape, which happened on February 9, 1864. 4 Quote, Everyone wanted to be first. In order to get down the chimney as well as the long tunnel, it was necessary to strip naked, wrap the clothes in a bundle, and push this on before them. As soon as it was seen that only a few men could possibly get out before daylight, all rushed for the mouth of the tunnel. Who could? Each man being determined to get out first. The room was now crowded to suffocation, all struggling to get in the hole. The strongest men forced their way to the front, while the weak ones were more roughly brushed aside and jammed up against the walls.
Holly Frey
Sneaden also made a map of the prison in watercolor, showing the prison, the tunnel route, nearby streets and other buildings, and the James river and its adjacent canal. That map is now in the collection of the Virginia Historical Society.
Tracy V. Wilson
In one account of this escape, during the roll call the next day, a Confederate official said, where are they all? And somebody answered, they fell out the window, which cracks me up.
Holly Frey
Whole lot of window drops. 109 men managed to escape through that tunnel, with more than half of them successfully making it to Union territory. Some of the ones who managed to evade capture had help from Union spy Elizabeth Van Lew, who was mentioned in our prior episode on Mary Elizabeth Bowser, which was a Saturday classic not Too long ago, 48 of the men were recaptured and two drowned while trying to cross a river. Colonel Rose, who had started the whole escape plan, was one of the ones recaptured and he was held at Libby until April 30, 1864, when he was released as part of a prisoner exchange.
Tracy V. Wilson
A few weeks after this escape, H. Judson Kilpatrick and Ulrich Dahlgren tried to liberate the prison, but they were discovered. Dahlgren was killed and papers he was carrying with him suggested that there was a plan in the works to burn down Richmond and kill Confederate President Jefferson Davis. After this, Richmond's Provost Marshal, John H. Winder, authorized Major Thomas Pratt Turner, who was commandant of the prison, to dig a pit under the prison, fill it with gunpowder and blow the whole thing up if there were any further escape attempts. That threat was never carried out. Soon the Confederate army started transferring men out of Libby to other prisons.
Holly Frey
After the war was over, the entire thing was dismantled and moved to Chicago, where it operated as the Libby Prison war Museum from 1889 to 1899.
Tracy V. Wilson
I have many questions about that, but I did not look into answering them because it was outside the scope of this podcast. We're going to take a quick sponsor break and then get to two more escapes.
Big Three Basketball Announcer
The reviews and ratings are in and Ice Cube's Big Three is the surprise hit of the summer. And to cap off the season, iHeart presents the Big 3 Basketball Championship and 8th Annual Big 3 All Star Game this coming Sunday, August 24th. Live from Orlando, the remaining two teams fight it out for the Big 3 Championship Championship Dr. J Trophy in the most physical, fierce and competitive basketball league in the world. Don't miss the wild conclusion of Big Three's eighth and most historic season ever. This is the game no one wants to lose and there's no crying in the Big three. The action starts with the Big Three eighth Annual All Star Game. Don't miss All Stars Dwight Howard, Montrez Harrell, MVP Michael Beasley, Lance will make you, Dan Stevenson, Jordan Crawford, Greg Monroe, Earl Clark, Nasir Kor and more show you why they are the best three on three basketball players in the world. Big three's exciting all star game plus the crowning of a new big three champion. The no holds part action starts Sunday at 2pm Eastern 11 Pacific only on CBS.
Holly Frey
Listen to your elders, honey.
Podcast Promoter
You might know them from their viral videos, but now the old Gays pull back the curtain on their brand new podcast, Silver Linings with the Old Gays, brought to you in partnership with iHeart's RWBY Studio and Vive Healthcare. With over 300 years of experience between them, hosts Robert, Mick, Bill and Jesse serve four lifetimes of wisdom when it comes to love, sex, community and whatever else they've got on the gay Agenda. Listen in to these fabulous friends, swap stories exploring how queer life has evolved over the decades and the silver linings they've collected along the way. Each episode dives into hot topics, from safe sex and online dating to untangling Gen Z lingo, as well as insights on how music, art and fashion show up in queer culture. So check out Silver Linings, a show about how pride ages like fine wine. Available on the iHeartRadio app or wherever you get your podcasts.
Ryan Seacrest
Hey, it's Ryan Seacrest for Albertsons and Safeway. Now through August 26th, it's back to Deals Time, where you can enjoy storewide deals and earn four times points. Look for in store tags to earn on eligible items from Kettle, Haagen, Dazs, M&M's Ritz, Chips Ahoy, Arrowhead, All Poppy, Charmin and Red Bull. Then clip the offer in the app for automatic event long savings. Shop in store or online for easy drive up and go pickup or delivery subject to availability restrictions. Apply. Visit Albertsons or Safeway.com for more details.
Lizzie Logan or Dana Schwartz
Have you ever looked at a piece of abstract art or music or poetry and thought that's just a bunch of pretentious nonsense? Well, that's exactly what two bored Australian soldiers set out to prove during World War II when they pulled off what was either a bold literary hoax or a grand poetic experiment, publishing over a dozen intentionally bad but highly acclaimed works of expressionist poetry under the name Ern Malley. In an incident that caused a media firestorm and even a criminal trial, the Ern Malley episode made fools of believers and critics alike and still fascinates poetry lovers to this day. We break down the truth, the lies, and the poetry in between on Hoax, a new podcast hosted by me, Lizzie Logan and me, Dana Schwartz. Every episode, Hoax explores an audacious fraud or ruse from history, from forged artworks to the original fake news. To try and answer why we believe, listen to Hoax on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Tracy V. Wilson
Next up we have Shiratori Yoshie who successfully escaped from four different prisons in Japan in the 1930s and 40s. English language accounts of these escapes have some contradictions. This was also true of Japanese accounts that I found and ran through Google Translate. But still, the basics and the places where they kind of intersect are just fascinating. He was initially imprisoned for burglary and murder in a crime that had been committed by a group of men. And he maintained that he had not been involved in the murder. And there are some accounts of this that describe him as falsely accused.
Holly Frey
His first escape was from Aomori Prison, after he'd been incarcerated there for about three years. He had found a piece of wire in a washtub, and he used that wire to pick the locks. He was caught just a few days later.
Tracy V. Wilson
Then, in 1942, he was transferred to Akita Prison. His cell had been designed to deter escape attempts, but he noticed that the wood around his skylight in the ceiling was starting to rot. So he climbed up there night after night, loosening the rotten wood. Then he waited for a stormy night to disguise the sound of his moving along the prison roof. And then he climbed up through that skylight he removed and then climbed out.
Holly Frey
Shiratori maintained that the accusations against him were false and that his incarceration was unjust. And then he went to the home of a police officer who had previously been kind to him. He had hoped that the officer would be willing to help him, but instead, the officer turned him in, and Shiratori wound up at Abashuri Prison.
Tracy V. Wilson
This was Japan's northernmost prison, and it was a place where some of the nation's most notorious people were housed. Even though the prison was supposed to be escape proof, Shiratori was kept handcuffed there, except when he was bathing for this escape. And this is the detail that made me put this on the list. Shiratori spit the miso soup from his meals onto his handcuffs and the meal slot in his door. If you've had miso soup, you know it's really salty. So he was wanting the salt in the soup to weaken the metal in his handcuffs. And that meal slot.
Holly Frey
This was during World War II, and the prison had huge skylights in the roof, so it was kept in blackout conditions at night. On the night of August 26, 1944, Shiratori broke through his weakened handcuffs and meal slot, reportedly dislocating his shoulders to do so, and escaped through the skylights under cover of darkness. Abashuri Prison is now a museum and has a model of Shiratori climbing to the windowed roof. To escape in his underwear. Although details are fuzzy about how exactly he climbed up to the skylights. If he had just dislocated his shoulders.
Tracy V. Wilson
Yeah, Even if he had popped his own shoulders back into place, that seems like it would have been incredibly painful and difficult to try to do because it was. It's not a low ceiling. It's like a very high ceiling with big skylights up there, regardless of the detail. With that, though, Shiratori hid in an abandoned mine until after the end of World War II. And then a farmer caught him stealing food from the fields and Shiratori stabbed him. The farmer later died of his injuries, and Shiratori maintained that the stabbing had been done in self defense.
Holly Frey
At this point, Shiratori had escaped from prison three times, and he had been convicted of committing other crimes in addition to that first robbery and murder during his escape. So he was sentenced to death. He was housed at Sapporo Prison to await his execution.
Tracy V. Wilson
Two of his previous escapes had involved climbing up through ceilings and roofs. So that was apparently where the guards focused when they secured his cell. So in 1947, he went out through the floor instead. He pried up the floorboards and then used again the bowls from his meals. He used them as shovels to shovel through the dirt underneath the floor.
Holly Frey
He was once again caught. That was about a year later, but this time, rather than adding to his sentence, again, a court ruled that Shiratori really had stabbed the farmer in self defense. After he had escaped from Abashiri Prison, his sentence was reduced to 20 years in prison and he was released in 1961. He lived free for quite some time. He died in 1979.
Tracy V. Wilson
Yeah, he, as I understand it, became kind of an anti hero in, in, in Japan because of all of this. And now we have one last escapee who is another man, but his wife is the one who should really be credited with planning it and carrying it out. This was William Maxwell, the 5th Earl of Nidsdale, who was probably born at Tergil's Castle in Scotland in 1676. His father had died when he was a child, and he was raised mostly by his mother, who was a Catholic and then later a Jacobite, that is a supporter of the Stuart claim to the British throne After the Stuarts were forced into exile during the glorious revolution of 1688.
Holly Frey
When William became an adult, he married Lady Winifred Herbert. They met while William was in France to pledge his loyalty to the exiled James II and seventh. And Winifred was visiting her father, who was one of the people who helped get James's wife and son out of England during the Glorious Revolution. Once they returned to Scotland, they tried to be discreet about their religion and their political views, since most of their neighbors were Protestants. But they were still the targets of suspicion. And on Christmas Eve 1703, a mob broke down the castle gates and ransacked the property, looking for any Catholics they might be harboring.
Tracy V. Wilson
Yeah, their political views also would have been treason. So it was very important to keep that very quiet. William was cleared of any wrongdoing after this mob breaking down his door, but he was stripped of one of his titles in order to pay a bond to ensure that he would not plot against the throne. Authorities kept him under close watch, and during all of this, he bequeathed most of his property to his eldest son. This might have been an attempt to protect that property from being confiscated if he were arrested again in 1715.
Holly Frey
William was part of the Jacobite rising of 1715. We have covered the Jacobite risings on the show before, and briefly, this was one of a series of failed attempts to restore the Stuarts to the British throne. William commanded a group of gentlemen volunteers, and after the Battle of Preston, he was one of almost 1500 Jacobites taken prisoner. In January of 716, he pled guilty to treason, and on February 9th, he was sentenced to be hanged, drawn and quartered. His execution was scheduled for February 21st.
Tracy V. Wilson
Winifred was determined to get him released, so she traveled to London. This was wintertime. When the snow became too deep for her carriage to get through, she finished the journey on horseback. She met with King George the First, clinging to his robes. When he refused to accept a petition on her husband's behalf, she refused to let go of those robes as he tried to walk away from her. And so he dragged her across the room. And as word spread about that, that wound up earning her some popular support. People did not like the idea that the. The king had dragged this distraught wife across the room.
Holly Frey
She bribed the guards at the Tower of London, where William was being held, to allow him to receive visitors and gifts. And she visited him repeatedly, often with the company of other women. On the night before he was to be executed, she arrived with her maid, Cecilia Evans, and her friends, Mrs. Morgan and Mrs. Mills. And she had brought women's clothes and makeup with her.
Tracy V. Wilson
As Winifred got William dressed and made up, she had a loud conversation with her friends about where in the world Cecilia had disappeared to. She knew exactly where Cecilia was. This was all part of a ruse meant to be overheard by the guards. Winifred's companions then left the prison one by one, and then they were followed by Winifred and William together, as though William were her maid. He was hiding the lower part of his face behind a handkerchief because they did not have time to shave him before leading him out.
Holly Frey
Oh, this is. I can think of so many comedy troops. I would love to see recreate this. Once William was outside, Winifred doubled back, went to his empty cell, and had a pretend conversation with him, closing the door behind her when she left. On the way out, she told the guards he was at prayer and should not be disturbed. The guards didn't even realize William was gone until everyone involved in this ruse was safely away from the Tower.
Tracy V. Wilson
Yeah, this whole thing really banked on causing the guards to be confused about exactly how many women had arrived with her and where precisely they were at any given moment. After getting out of the Tower, William took refuge at the Venetian embassy, and then he escaped to Dover while dressed as a Venetian ambassador. He went to Bruges by boat and then to Paris, where he reconnected with his wife. The two of them became part of the Stuart court in exile. In 1717, they moved to Rome, and that is where William died in 1744. William had a reputation for always living beyond his means, and he died in debt. But Winifred became a popular heroine in Jacobite writing. She died in 1749.
Holly Frey
All right, if you're thinking, hey, why wasn't the John Dillinger escape in here? That was pretty ingenious. Yes, that's true. But there is an episode on Dillinger already that is going to be an upcoming Saturday classic.
Tracy V. Wilson
Yeah, seemed like a good thing to add in there since they do talk about that escape in that prior episode. Thanks so much for joining us on this Saturday. Since this episode is out of the archive, if you heard an email address or a Facebook URL or something similar over the course of the show, that could be obsolete now. Our current email address is historypodcastradio.com you can find us all over social media. Mistinhistory and you can subscribe to our show on Apple Podcasts, Google Podcasts, the iHeartRadio app, and wherever else you listen to podcasts. Stuff youf Missed in History Class is a production of iHeartRadio. For more podcasts from iHeartRadio, visit the iHeartRadio app, Apple Podcasts, or wherever you listen to your favorite shows.
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Tracy V. Wilson
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Episode Date: August 16, 2025
Hosts: Tracy V. Wilson & Holly Frey
In this classic episode, Tracy and Holly bring listeners a collection of six remarkable prison break stories. Instead of focusing on violent or infamous escapes, the hosts highlight inventive and often ingenious attempts—many with a “Shawshank Redemption” vibe. Each tale, rooted in different historical contexts and countries, illustrates the creativity, determination, and resourcefulness of those desperate to regain freedom. This curated collection balances dramatic escapes, clever ruses, and even a bit of dark comedy, perfect for fans of history — and jailbreak intrigue.
"I was really focused on escapes that seemed particularly ingenious and how they were planned and carried out, not on ones that were violent." — Tracy (03:52)
[04:51–10:48]
"The system that they devised was innately cruel. It came to be known as the Pennsylvania system. And it was basically perpetual solitary confinement." — Tracy (05:31)
"He shored it up with wood and installed lights and ventilation fans. When the tunnel intersected with a sewer pipe under the prison, they built a connection... so they could dispose of their waste." — Holly (07:55)
"Most of them though, were back in the prison within a day and all of them had been caught within a few months." — Tracy (08:44)
[10:48–14:57]
"Only a small number of people who were sentenced to transportation had been convicted of a violent crime. A lot of them had been convicted of offenses that most people would think of as pretty petty today." — Tracy (11:42)
"These women made a habit of singing and quote, noisy vociferations after dark. ...someone had provided them with a file, some nitric acid, also called aquafortis..." — Holly (12:23)
"It appears that with one possible exception, all of the women involved in this prison break did wind up being transported to Australia." — Tracy (14:13)
[18:15–24:02]
"They made a 6 foot by 14 foot raft out of about 50 raincoats. ...Some of the men were happy to... leave them there to be picked up, kind of donating them to this effort..." — Tracy (20:43)
"But then what happened to them after that is a mystery." — Tracy (22:54)
[24:24–29:40]
"Because all the rats and the ongoing flooding problems made the cellar smell terrible so so bad that it was nicknamed Rat Hell." — Tracy (25:38)
"Each man being determined to get out first. The room was now crowded to suffocation, all struggling to get in the hole." — Robert Knox Sneaden, historian (26:51)
[33:33–37:41]
"He spit the miso soup from his meals onto his handcuffs and the meal slot in his door. If you've had miso soup, you know it's really salty. So he was wanting the salt in the soup to weaken the metal." — Tracy (35:13)
"He pried up the floorboards and then used... bowls from his meals... to shovel through the dirt underneath the floor." — Tracy (37:19)
[38:06–43:29]
"As Winifred got William dressed and made up, she had a loud conversation with her friends about where in the world Cecilia had disappeared to... This was all part of a ruse meant to be overheard by the guards." — Tracy (41:40)
"This is more Shawshank Redemption than horrible riot situation." — Holly (04:37)
"Each man being determined to get out first. The room was now crowded to suffocation, all struggling to get in the hole." — Robert Knox Sneaden (26:51)
"He spit the miso soup from his meals onto his handcuffs and the meal slot in his door. ... to weaken the metal..." — Tracy (35:13)
"This whole thing really banked on causing the guards to be confused about exactly how many women had arrived with her and where precisely they were at any given moment." — Tracy (42:42)
"Where are they all?"
"They fell out the window, which cracks me up." — Tracy (27:52)
| Segment/Topic | Timestamp | | ---------------------------------------------------------------- | --------------- | | Introduction & episode premise | 02:09–04:51 | | Eastern State Penitentiary (Philadelphia) | 04:51–10:48 | | Limerick Jail (Ireland, women’s escape) | 10:48–14:57 | | Alcatraz Escape (San Francisco Bay) | 18:15–24:02 | | Libby Prison Civil War Escape (Richmond, VA) | 24:24–29:40 | | Shiratori Yoshie (Japan, multiple escapes) | 33:33–37:41 | | Lord & Lady Nithsdale, The Disguise Escape (Britain, 1716) | 38:06–43:29 |
True to the podcast's style, the tone is witty, anecdotal, and compassionate, with respect for historical context and a focus on the human side of bizarre events. The hosts balance levity with insight, pointing out foibles and ironies without trivializing their subjects.
"If you're thinking, hey, why wasn't the John Dillinger escape in here? That was pretty ingenious. Yes, that's true. But there is an episode on Dillinger already..." — Holly (43:29)
This episode is a whirlwind tour through a wide array of ingenious prison breaks, illustrated with period details, sharp quotes, and historical context, making it a treat for history buffs and fans of clever capers alike.