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Main Narrator
Refreshers contain caffeine. On the night of 12 June 1962, just like every other night, the Alcatraz night guards hit their patrol. They shone their torches into every one of the prison's 300 cells to check that nothing untoward was happening. This was Alcatraz, after all. The Rock Devil's Island. Its name struck fear into the hearts of the nation's worst criminals. Previously a military fort, it had become a kind of symbol in the US's war on crime. It was home to the worst of the worst gangsters, murderers and problem inmates from across the country, including John Anglin, Clarence Anglin, Alan west, and Frank Morris. They'd been sent to Alcatraz because, well, they wouldn't stop trying to escape from all the other prisons they'd been put in. So these four perpetual prison breakers found themselves on this barren island, separated from the San Francisco shoreline by a mile of freezing, fast moving ocean water. Escape was said to be impossible, but to these four, that was just too much of a challenge to pass up.
Co-Narrator / Commentator
That night, everything appeared to be in order. Frank Morris and the Anglin brothers seemed to be sleeping soundly in their cells, but in the morning, they were gone. In their place were dummy heads made of plaster, soap dust, toilet paper, toothpaste, and most disgustingly of all, real human hair collected from the prison barbershop. They'd been touched up using paint from the maintenance workshop. Pillows and clothes had been arranged under the covers to look like their bodies. The prison was locked down. Over the next few days, more fragments of clues washed up on the shore in the shadow of the golden gate bridge. Those clues included homemade wooden paddles and a raft made from more than 50 stolen and sewn together raincoats. More and more ingeniously crafted items washed up, too. But the men were nowhere to be found. This is the shorthand, considering the rogues
Main Narrator
gallery of hardened criminals that called this island home. Its first residents were a little less intimidating. In 1775, a Spanish naval officer named it la isla de los Alcatraes. Alcatraz being the old Spanish word for pelicans. But the birds would eventually have to give up their prized rock. First, a lighthouse was built to guide ships coming into San Francisco Bay. Even then, it was still considered a bit of a random outcrop. Its nearest settlement, San Francisco, was at the time just a sleepy little village. But then in 1848, someone saw something shiny in a river in northern California, and, well, the fate of the entire region was forever changed.
Co-Narrator / Commentator
The gold rush brought people and ships flooding in from all over the world into the San Francisco bay. The village of 300 boomed into a city of more than 30,000. And suddenly the whole region was very, very valuable indeed. The state of California had only just become US Property, and they wanted to keep it that way. So the president signed an executive order claiming Alcatraz island. He ordered the construction of a giant fort on it to keep a lookout for interlopers. It had a high central citadel, complete with actual drawbridge and moat. And dozens of cannons were placed on the outside. Any ships heading into San Francisco would come within a mile of the most powerful fort west of the Mississippi. And when the civil war kicked in in 1861, 10,000 muskets and 150,000 cartridges of ammunition were sent to the island to defend it from those pesky confederates. But mainly, the fort sat manned but totally inactive for decades. And by the end of the civil war, with weapons technology getting more and more advanced, having a big citadel surrounded by cannons wasn't the flex it had been before.
Main Narrator
So the government started to look at the fort's other strengths, Namely, isolation. Its high walls, barren rocks, and mile of freezing ocean separated it from the big city, making it the perfect prison. Its first inmates were people captured during the civil War. Confederate sympathisers, deserters, and civilians accused of treason. But soon enough, it was also full of all sorts of miscreants, escapees, thieves and drunkards. It was expanded to fit all these new lost souls. The prison that stands there today was literally built on top of the original citadel. And back then, despite the poetic distance from the shore, conditions weren't so bad. It was actually a minimum security facility and many prisoners were relatively content doing the various jobs that they'd been trained up to do. But then in 1934, the prison was made a federal penitentiary, which marks the real beginning of its villain origin story.
Co-Narrator / Commentator
1934 was a real banner year for crime. It was the tail end of the Prohibition era, a heady time of underground clubs, bootleg ligger and seedy gangs. Which is also the reason we have cocktails to make bathtub gin palatable. And I'm not mad. It had brought with it a new breed of organised criminal. What's more, the Great Depression was also well underway. The state of general desperation led to a surge in theft, robbery and violent crimes. And it introduced a new kind of high profile outlaw like John Dillinger and Bonnie and Clyde figures who became folk heroes to a beaten down public, which led the FBI to up the ransoms and crack down further, which only served to make these outlaws even more infamous. A major and very public war on crime had reached its absolute peak and the government was keen to be seen to be doing something about it.
Main Narrator
And that context is important because Alcatraz's infamy didn't just come naturally. It wasn't developed over years through horrifying stories from the inside. It was baked in from the start. In a way, it was a kind of PR stunt, a marketing scheme the government had set out for a place with zero link to the outside world. Originally, they were actually eyeing up a bit of land in Alaska, but then Alcatraz became available and it was perfect. So they set about turning Alcatraz, this citadel on this rock, into a national island of exile and a new, tough as nails prison for the worst of the worst. One with new, tougher iron bars and an unforgiving daily schedule. And I've actually been to Alcatraz and have to say I was kind of disappointed.
Co-Narrator / Commentator
Were you? I don't think I. No, I haven't been around it. I've seen it from afar.
Main Narrator
Yeah, see, I went and I was kind of disappointed because I was just like, they don't tell you they're like fun, grizzly stuff. They kind of like the PR continues. They kind of soft soap it and they're like, oh, this was where all the prisoners sat and ate together. And, you know, it was all Kumbaya. And I was like, what? I want to hear about all the fucking mental shit that went down. And they were just like, none of that ever happened here. What are you talking about? So, yeah, I don't know. I was like, ugh. It just felt like a whitewash.
Co-Narrator / Commentator
The prisoners were checked on a dozen times a day, and most days weren't even allowed to talk to each other. It was a monotonous and highly structured daily routine. Alcatraz's prisoners had four food, clothing, shelter and medical care. Everything else was a privilege that had to be earned. That included correspondence with family members, access to the library, work, and recreational activities like painting and music. The prison was soon filled with the kind of prisoners that fit that narrative. Anyone who was deemed too difficult or violent or couldn't stop trying to escape was shipped off to Sean Connery's the Rock.
Main Narrator
And for the government's high profile solution, they needed some high profile residents. Just a year after it opened, they welcomed Scarface himself, Mr. Al Capone. Alphonse Gabriel Capone, to give him his full name, rose to infamy during the prohibition era. He ran wide scale gambling, prostitution and bootlegging rackets in Chicago and tightened his grip by massacring enemy gangs. He was the FBI's first public enemy number one. And his arrival at Alcatraz was big news. The San Francisco Chronicle reported Capone sagged at his first glimpse of the prison.
Co-Narrator / Commentator
If anyone ever described me as Hannah McGuire sagged, I think that's all the prison sentence.
Main Narrator
I need it out. I mean, come on. Could we not have thought of a better. Capone withered as he saw the first clip. Sagged.
Co-Narrator / Commentator
Come on now.
Main Narrator
But anyway, true to form, at other prisons, Al Capone had been big on bribery and special treatment. But he had no such luck at Alcatraz. So deprived of any opportunity for some Machiavellian string pulling, he got another hobby. Pulling another kind of string. He started a band called the Rock Islanders. This is the kind of bullshit they were telling me on the fucking tour. I was like, I what? I don't believe you, but maybe it's true. So, yeah, they had a fucking band. And apparently Mr. Al Capone himself was on banjo. He boasted in a letter to his son that he'd Learned more than 500 songs.
Co-Narrator / Commentator
I went to a music store this morning to replace my broken boom arm and, like, try and get a rodecaster that's surprised, doesn't work. And there was a poster in that was like restring your axe. And then it had like prices for each type of guitar. And it also had banjo and ukulele. And I was like, I don't know if you can call those axes on the same list as like mega fuck rock guitar. Like, you know, But I mean, maybe they need to feel, they need to feel heavy too, you know?
Main Narrator
Yeah, I feel like it's more of like a Swiss army knife compared to a guitar.
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Co-Narrator / Commentator
Other high profile inmates followed from Machine Gun Kelly, Prohibition era gangster, not fuckboy rapper. And then there's the rock's most famous prisoner of all, Robert Stroud, the so called Birdman of Alcatraz. And I have been sucked in by Birdman. And I follow this statement with my whole heart. There's a lot to say about the Birdman. A lot of it's quite boring. He's not actually as interesting as he may seem.
Main Narrator
Just like the fucking prison.
Co-Narrator / Commentator
He was a violent prisoner who became an expert on canaries and he kept them in his cell. And that is kind of it.
Main Narrator
I really feel like they branded this whole prison so well that we're all still obsessed with it. And please do keep listening, please don't listen to me. Keep telling you that this is incredibly boring. Our episode is interesting and this is more interesting than the one hour tour I did there. But yeah, I don't know, dunno.
Co-Narrator / Commentator
He's not called Birdman because he tried to escape on homemade wings like Icarus. It's just because he Liked birds just
Main Narrator
because of the canaries.
Co-Narrator / Commentator
Got it. The punishing side of Alcatraz is easy to romanticize. Some of the country's most feared criminals are out there on the bay, isolated from civilization and across the country. It was used as a deterrent to keep other prisoners in line. The main headline was Alcatraz is like Azkaban, inescapable. And obviously the idea of that PR was to strike fear into the inmates. But also they'd just gathered all of the nation's prisoners together who were the most obsessed with escaping and gave them a challenge. Exactly. They gave them a challenge and nothing else to do. And repeatedly told them that they would never ever escape.
Main Narrator
Arts and crafts is a privilege. Thinking about escaping is a privilege. But Al Capone on the banjo, off you go. So, yes, it's a mile of freezing cold ocean water that can have very, very, very strong currents. But the swim from Alcatraz to San Francisco is far from impossible. In fact, in 1934, just before the prison opened, a 17 year old girl swam from Alcatraz to the Mainland in just 47 minutes just to prove that it was possible.
Co-Narrator / Commentator
It's not fun, but you can do it.
Main Narrator
She did it. Now, the FBI probably weren't thrilled about this little stunt right before they opened their big, bad inescapable prison. Still, that swim was done with the benefits of lots of swimming practice, a decent diet and knowledge of the types of. It's a lot harder in the dead of night. After months of prison rations during Alcatraz's time as a federal prison, the number of successful escape attempts is officially none. Now, we'll come back to those plaster heads very soon. But interestingly, back when it was a minimum security military prison, as many as 28 prisoners may have successfully escaped. In 1903, four prisoners forged fake release papers and left through the front door. And in 1901, one prisoner floated on a wooden board for eight hours before he finally reached the shore. In 1921, two prisoners literally set off into the bay in a kitchen sink. And guess what? They made it. And then three years later, in 1924, the prison put on a play for San Franciscans from the mainland. And three prisoners stole costumes and left with the audience like they were in some sort of fucking Wes Anderson film.
Co-Narrator / Commentator
But the real challenge was escaping from the maximum security civilian prison. And from 1934 until the prison was closed in 1963, 36 men attempted 14 separate escapes. Of these, 23 were caught, six were shot and killed and two drowned and five went missing. Some bent or soared through the bars before climbing through and attempting the swim. One took advantage of his job working in the laundry. He stole an entire army uniform and calmly walked out onto a boat, which left without missing a beat. He thought he had smashed it, but unfortunately, the boat was not headed to the mainland. It went straight to nearby angel island, where correctional officers recognised him and returned him to the rock. Bummer, bummer.
Main Narrator
You'd be so pissed.
Co-Narrator / Commentator
In 1946, six prisoners overpowered a group of officers and took them hostage. They got access to guns and keys and took control of the cell house. More guards arrived and the prisoners decided to take them on, starting what became known as the Battle of Alcatraz. Over the next few hours, there were a series of shootouts. They shot their hostages and even freed more than a dozen other inmates. There was just one more door between them and the boat that would take them to freedom, the one to the recreation yard. But they didn't have the key. All the escaped prisoners were recaptured and two of the perpetrators were sentenced to death.
Main Narrator
All of which leaves just one almost unbelievable story of daring and ingenuity. And it's the escape. The one featured in the 1979 movie Escape from Alcatraz, starring Clint Eastwood as Frank Morris. The real Frank Morris arrived in Alcatraz in January 1960. He hadn't really had much of a chance in life. Abandoned by his parents at 11, he got his first criminal conviction at 13, and his life from that point on was a string of armed robberies and home burglaries. He was in and out of prison and had a reputation for constantly trying to escape. So he was sent to the rob. Later that year, two brothers called John and Clarence Anglin were put in the cell next door to him. They'd grown up dirt poor and also got the robbing itch pretty young. And similarly to Morris, once they started being sent into prisons, the brothers couldn't stop trying to prize their way out. Same story for the next cellmate down, Alan West. The four of them had gotten to know each other in previous prisons and now they were neighbours with nothing to do apart from chase. The biggest prize in the escapee handbook,
Co-Narrator / Commentator
Alcatraz, one freezing cold December. One of them came across some old saw blades and stuffed them into his pocket. Another stole the motor out of an old vacuum cleaner. Using the blades and the motor and some old spoons, they fashioned themselves a drill. They took it in turns to use that drill to loosen the air vents at the back of their cells, not by undoing screws. Just by drilling loads of small holes until a whole section of the wall could be removed to mask the noise. They just waited for Music Hour. When Morris would play his accordion over. The music pumped into the cells. Then they covered the vents with painted cardboard. Those vents opened onto an unguarded corridor, which led them up to the top level of their cellblock. And every night, they'd pop a plasterhead on their pillow, head upstairs, and get to work. They used more than 50 stolen raincoats to build a sizable rubber raft and four life vests. These were stitched together and then sealed on hot steam pipes in the loft. They modified Morris's accordion into an air pump to inflate the raft. That's incredible. Thank God he played the accordion and not the ukulele.
Main Narrator
The spoon of the guitar world.
Co-Narrator / Commentator
The accordion's really fucking hard. It's a really difficult instrument.
Main Narrator
Yeah, yeah. There was a girl I went to school with that played the accordion, and I was like, very niche.
Ryan Reynolds (Mint Mobile Advertiser)
Yeah.
Main Narrator
But, yeah.
Co-Narrator / Commentator
They made paddles out of some wood that they swiped. And by the evening of June 11, 1962, everything was ready. And the four of them readied their plaster heads as well.
Main Narrator
But there was one hitch. Alan west had used cement to temporarily reattach his vent. Turned out that cement wasn't exactly temporary. He scrambled to use the drill to remove the vent again from scratch, but it was too late. So he just went back to bed and left his co conspirators to it. The other three, Morris and the Anglin brothers, went on through a ventilation shaft and onto the roof. From there, they climbed 50ft down a series of kitchen pipes to the ground. They vaulted over a 12 foot barbed wire fence and headed down to the northeast shore. They used their accordion pump to inflate their raincoat raft and set off. And they were never seen again. Once the morning check revealed them to be gone, the prison was locked down. The FBI immediately got to work interviewing relatives and searching the shore. Two days after the escape, they found a packet of letters in the bay sealed in rubber. Then some paddles and a life vest washed up, too. But it wasn't till they got Alan west to fess up that they pieced together the full story. We've just told you.
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Main Narrator
Refreshers contain caffeine.
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Co-Narrator / Commentator
And officially, there have been no successful escapes from Alcatraz. But that's only because the FBI concluded that the three men didn't make it. They reasoned that, firstly, the odds were against the prisoners, already with freezing water and strong currents. Plus, their plan had been to steal clothes and a car. But no matching thefts had been reported on the shore. And after 17 years of investigation, with no sign of the men, they officially closed the case on December 31, 1979. But luckily for us, there are many people who disagree with that official report. As early as December 1962, the year of the escape, the Anglin family reported having received Christmas cards from the brothers. Their mother says that she received anonymous flowers on her birthday every year until she died in 1973. Two tall men in heavy makeup are even said to have attended her funeral. And there are plenty of other reported sightings too, including inmates who said that they had helped. One even said that he arranged to pick them up and then he murdered them so he could keep the money that their families had given him to pass on. And then there's a photo which I'm looking at. It's of two men who look like two men. It's like if you drew a picture of two men, that's what it would be. One blonde, one. One brunette. Two men standing next to a rock and a tree. That's what you've got. This photo comes from a family friend who says that he met the brothers in Brazil in 1975. It's blurry and they're wearing shades, but it does kind of maybe look like a picture of two men. And of course, it's possible that these stories are inflated or just people wanting to be attached to the legend. But I don't care. I want to believe.
Main Narrator
Accordion inflate me. Give it to me now. Despite Alcatraz's infamy, just over 1500 people were ever imprisoned there. In the 29 years that it was a federal prison, there was never more than 260 prisoners there at any one time. And eventually the PR effects of the prison's island location started to be outweighed by, well, the sheer enormous cost of having a facility in the middle of a bay. Because of its location, it was three times more expensive to operate than any other prison. Everything had to be brought in by boat, including a million gallons of fresh water every week by barge. In 1963, the prison was ordered closed. As for what to do with it next, there were plenty of ideas. Hotels, malls, and even a West coast version of the Statue of Liberty. But as you probably know, it eventually became a tourist attraction which welcomes more than a million visitors every year.
Co-Narrator / Commentator
If you hadn't told me that it was really boring, I would want to go.
Main Narrator
Don't go. Sorry, Alcatraz Tourism Board.
Co-Narrator / Commentator
But I was bored.
Main Narrator
Source it up a bit. I want to hear about, you know, like, put a guy in a hat and say there's ghosts. That's what people want to hear. Fuck it.
Co-Narrator / Commentator
Hell.
Main Narrator
So tepid.
Co-Narrator / Commentator
And that is where we're going to have to leave it. So for anyone who came into today's episode hoping that we'd cover the takeover of the island in the early seventies by Native American activists. So it's not this time. Maybe another day, because it is far too cool to gloss over. And another shorthand will be coming down the line. So come back for that. The story of their 19 month occupation which caused massive changes in federal policy and kick started the red power movement. For now, we're going to leave you with a quote from the last prisoner to leave Alcatraz. As he stepped onto his boat in front of a crowd of reporters and photographers, he looked up and told them Alcatraz was never no good for nobody. Apart from the tourism board, apparently.
Main Narrator
Yeah, because they're fucking dining out on that boring shit, I'm sure. Anyway, that's it guys. We hope you learned something. And you should go watch the rock instead of going to do a tour of Alcatraz. Do that instead and we'll see you next time.
Co-Narrator / Commentator
Goodbye. Goodbye.
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This episode sponsored by Eureka Ergonomic. Why should your standing desk make your home feel like a fluorescent lit cubicle? You've worked hard to make your space feel warm, clean and intentional, so your desk should fit right in. That's why Eureka Ergonomics stands out. Eureka Ergonomic creates standing desks. Ergonomic chairs and workspace furniture that look beautiful in your home and feel great to use every day. Choose from designs that blend into your home while giving you the height, adjustability, and support you need every day. With Eureka Ergonomic, you're not choosing between style and comfortable you get both. Visit Eureka ergonomic@eurekaergonomic.com. that's E U R E K A ergonomic E r G o N o M I c dot com and find a standing desk that works hard without making your home feel like a cubicle.
Release Date: July 21, 2026
In this richly detailed and darkly witty ShortHand episode, the RedHanded hosts dive into the infamous history of Alcatraz Island—“The Rock,” or “Devil’s Island”—with their trademark blend of macabre curiosity and dry humor. Focusing especially on the legendary 1962 escape, the episode explores Alcatraz’s evolution from bird-covered outcrop to military fort, then notorious penitentiary, capped off by its transformation into a pop culture icon and tourist trap. The hosts lay bare the prison’s myth-making, some disappointing truths, and the real and rumored stories behind its most famous inmates and escapes.
Historical Evolution ([03:38] – [05:32]):
Early Conditions and Upgrades ([05:32] – [08:54]):
Al Capone and Prisoner Life ([09:30] – [11:36]):
Other Notable Inmates ([12:47] – [13:44]):
Challenges and Escapes ([14:42] – [16:37]):
The 1962 Escape: Ingenuity and Legend ([18:12] – [22:13]):
Did They Make It? ([23:18] – [25:08]):
Alcatraz’s Closure & Tourist Legacy ([25:08] – [26:23]):
| Timestamp | Content | |---------------|-------------| | 01:19 | Opening recount of the 1962 “impossible” escape by Morris and the Anglin brothers | | 03:38 | Founding and military history of Alcatraz (“la isla de los Alcatraes”) | | 05:32 | Transition to a prison, minimum security days, shift to federal penitentiary | | 09:30 | Arrival of Al Capone, “star power” inmates and their lives inside | | 13:44 | Birdman of Alcatraz and the creation of the prison's mythos | | 14:42 | Psychological warfare of “inescapability”; pre-1934 successful military prison escapes | | 16:37 | Maximum security escapes, The Battle of Alcatraz | | 18:12 | Detailed breakdown of the 1962 escape plan and execution | | 23:18 | Theories and myths surrounding the missing escapees and their possible fates | | 25:08 | Closure of prison, tourist site legacy; hosts’ dissatisfaction with the tour | | 26:23 | Mention of Native American occupation and Red Power movement—subject for future episode | | 27:03 | Final quote from the last prisoner |
The hosts interweave chilling facts, sardonic humor, breezy but insight-driven tangents, and moments of raucous commentary—mocking sanitized tourism narratives and skewering pop culture embellishments, while feeding listeners with well-researched dark historical detail. Their engagement keeps even “boring” facts lively, making the episode as entertaining as it is informative.
The episode delivers a thorough, irreverent, and myth-busting ride through the infamous legacy of Alcatraz, from its feathered origins to escape lore and modern tourist trap reality—never losing sight of the dark comedy in the difference between the prison's engineered reputation and what actually went down on “the Rock.” If you love true crime with snark, skepticism, and a splash of history, this one’s for you.