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Episode 1 – Willie Sutton

Sutton was the most prolific bank robber in the history of the United States. He robbed over 100 banks, his creativity and flair earning him the nickname ‘The Actor’. He was also number 1 on the FBI most wanted list, escaped prison several times, and did it all without shooting at anyone.


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    Full Transcript:

    I’d like you to pretend that this afternoon, you and your best mates are getting together to plan a bank robbery. How do you do it? Do you sneak in through the roof mission impossible style? Do you talk your into the vault like Oceans 11? Or do you dive in with machine guns and blast the place apart like in Heat? Heat is the only one of those based on real life, by the by.

    What’s your escape plan? Who is the driver? How many people do you need? Do you need to launder the money? Can you launder the money? Will you need to disappear for a while?

    It’s a lot to think about.

    But take heart! The FBI reckons that first time bank robbers get away with it 75% of the time. It’s only with subsequent heists that you raise the risk of getting caught. By the time you’ve done 4 bank jobs, there’s a 50/50 chance you’ve been caught.

    But what if you didn’t stop at 4 bank jobs? What if you committed 100? What if you spent you’re entire life planning heist after heist? Who would you be? What does that look like?

    That was the life of William Francis Sutton, the most prolific bank robber who ever lived.

    Sutton was born in Brooklyn in 1901. He was the son of Irish immigrants. He was an excellent student and came from a good home. His entire extended family was in honest work, they were were loving and supportive, and even though they were poor, never failed to provide for their kids.

    Brooklyn back then was an Irish ghetto. It was dirt poor, crime ridden and violent as hell. Despite coming from a good home, the neighbourhood had the greater influence on him, and he turned to crime from a really early age. When he was 12, he broke into a department store at midnight and raided the register. He says in his biography that he blew it all on candy and soda.

    He wanted to go off to college to become a lawyer when he left school, but his folks couldn’t afford it, so he got a job at an insurance company instead. Said insurance company had an internal banking department, and Sutton got to spend his late teens learning how bank security worked.

    He switched jobs and started stealing postage stamps from the mailroom to resell on the black market. It was going great, until some of his coworkers got caught doing the same scam. Sutton says that he felt super disappointed when they were fired because it meant that the clever scheme that he had come up with was very obvious. He liked to think of himself as a really cunning guy, and discovering he was average was a blow to his ego.

    His first arrest came when he broke into his girlfriends dads house. He was dating a very catholic girl that didn’t want shag unless she was married. Sutton needed money for that to happen, so he broke into the dads safe one night and made off with about 100,000 usd in todays money. He was 18 years old, so naturally he spent the money in the dumbest ways possible. He bought a mink coat for his girlfriend, a bunch of suits and shoes, and he bought a brand new guy even though he had no idea how to drive. The car lasted about 100 miles before he completely cooked the clutch, and the pair were arrested at some little town in Northern New York, just south of the Canadian border.

    They get whisked on back to New York, and Sutton gets offered an amazing deal by the dad. He gets off with probation as long as he promises never to see the girl ever again. Remember, he stole 100,000$ off this bloke.

    He takes the deal, as you would, and then immediately heads back into crime. He and two friends, most notably a guy named Eddie Wilson, who will feature prominently in this story, start running illegal gambling houses and dance halls. It’s not crazy lucrative, but they were doing ok, until one night Sutton has a to kick a guy out of one of his clubs. The mans name was Happy Gleason, and Sutton had to fight him out on the front steps to get him to leave. Sutton won, but it became common knowledge that he and Gleason had bad blood.

    The trouble was Gleason was a dickhead. He was both a thug and a police informant, and everyone hated him. One night, someone gunned him down with a shotgun.

    The police decided that Sutton & Wilson were the main suspects, and put out a warrant for them. Brooklyn PD weren’t known for their careful casework; more often than not they simply decided on a suspect, arrested them, and beat a confession out of them. Rather than get railroaded for a murder they didn’t commit, Sutton & his mate left town.

    And by ‘left town’ I mean the caught a bus over the Brooklyn bridge all the way to Manhattan, where the Brooklyn PD had no jurisdiction and the Manhattan cops didn’t care. Moving 6 miles away was enough to escape a murder charge in 1920.

    Sutton tried to stay clean for a while. He had a bunch of normal jobs, but each time he was tempted back to his old line of work. He was a welder at a shipyard for a while, it got him thinking about how to cut open a safe. He hung out with actors and chorus girls, and became really interested in makeup and costumes. He loved the way that you could make yourself look like anyone.

    His last honest job was repairing burglar alarms. He took it to get better at breaking burglar alarms. He didn’t last long though. One night, a gang busted in and blew up the company safe. The company hired private detectives, who decided Sutton was the prime suspect. He couldn’t stick away to face questions because of the small matter of him being a fugitive, so he changed his name and moved up town.

    He describes this point in his life as the moment he became a professional thief, the kind of man that wakes up in the morning with every creative impulse pointed towards finding that perfect heist.

    His next job was a simple one. Willie spent a few days watching a jewelry store and came up with a plan. He learned the manager came in an hour before the shop opened to organize it for the day. Willie came by with a valuable watch, tapped on the window, and insisted that it needed to be repaired immediately. The owner opened the door and was greeted by a pistol. Willie was able to calmly clear out the safe, secure in the knowledge nobody would be coming by for at least another hour. He only made off with about half as much as he expected though – his partner on the job had chickened out at the last minute. This was a harbinger of things to come, for throughout Suttons criminal career, his was one great weakness would be his partners

    He used the same technique at a shoe store for 800$, and an insurance company for another 1000$. Big money in the 1920s. But these robberies weren’t much more than simple stick up jobs, and as a smart guy, he craved something a little more challenging. It came it him courtesy of his Eddie Wilson. Wilson had started working with an elite gang of safe crackers known as the Tate gang, run by Doc Tate, a master thief. Tate was well dressed elegant man in his 40s. He suffered from Rheumatism that often interfered with the steady hands he needed to break locks. “Anything with a hole in it can be picked” he would often say. He hated violence, and took more of a cat burglar, after hours approach to his robberies. Willie and he hit it off immediately, and before long they were cracking safes up and down North East. Their MO was simple: Pick a town, pick 6 or 7 businesses, case them thoroughly, and hit them all in 1 or 2 nights. They never worked their home base of New York City.

    These smaller towns were easy pickings. They simply didn’t expect to be hit by such sophisticated robberies. On one heist in Boston, they were interrupted by a janitor working late, and had to scurry out the side window. On their way out of the alleyway, Willie passed a policestation with an open window. He peered inside, and saw an officer manning the late night desk. Willie left his jimmy and lock picks behind as a joke. The next day, he bought the paper. A journalist had found the tools before the police did, and wrote a scathing article attacking the Boston PD. Willie kept a clipping with him for years.

    They were making an easy 2000 a month each, but the good times weren’t to last forever. The crew were spending as much as they were making. Doc Tate was boasting to everyone who would listen about what a master thief he was, and was blowing up a considerable gambling debt. Willie followed his Aunt Alice’s tastes, and spent big on clothing and culture. He became a regular in the Broadway theatre crowd and threw lavish parties at his upscale midtown apartment.

    Manufacturers were catching up as well. To protect the tumblers, which are the internal parts of a safe that align the lock, they began to install heavy shielding plates. When that failed, they began using hardening agents to make the plates increasingly tough for drills to crack. Willie knew that eventually, the old methods of delicate safe cracking were going to fail, and so he began improving his metallurgy skills, preparing for the moment when welding would be the only option.

    The end to their partnership came with a robbery on the Roger’s Brother’s department store in Scranton, Pennsylvania. Tate had estimated it at an easy million dollars, their biggest score yet, but Willie had reservations. They alarms were top notch, and the store’s safe was essentially impervious to drilling. Willie told Tate that welding torches would be the only way forward, but Doc Tate was a vain man. He couldn’t tolerate the notion that his safe cracking skills weren’t up to the task, and as the leader, he forbade the use of welding.

    Willie had to move quickly after the break-up of the gang. His lifestyle was expensive and he was running out of cash. He performed a daytime heist on a jewelry store that was right outside a courthouse. His reasoning was that no one would expect daylight robbery to occur with so many police around. He walked right in while the store was open, locked the front door, cut the display open and took a bag full of diamonds, all without anyone noticing – the store clerks included.

    A week later, Willie & Eddie were at a baseball game. It was springtime, and the pair of them had their usual box seat at a Dodger’s Game. Sometime in the 3rd innings, Willie was interrupted by a clap on his shoulder. It was the Pinkerton detective agency, and they had questions for the pair of them about the Edison Company safe.

    They were dragged to a police station and interrogated. Eddie managed to talk his way out of it, and the moment he was free he ran back to Willie’s apartment, cleared it out of any evidence, and phoned lawyers for them both. Willie wasn’t so lucky. They held him on suspicion, fingerprinted him, and discovered his true identity. They shipped him back over the river where the detectives from his old precinct received him with glee. He was still wanted for the murder of Happy Gleason. Sam Todd, the head detective on the case, picked Willie up and hurled him down a flight of steel stairs. “It was a miracle I didn’t fracture my skull” he would later say. He was then tied to a chair and beaten with a rubber hose until dawn, but he didn’t break under the torture. Though Willie was guilty of an awful lot of things, he was no killer.

    They held him for a full 9 months in a Brooklyn jail until his trial, which was heard at the NY State Supreme Court. Happy Gleason’s friends from the evening stood as eyewitnesses that Willie was the killer, while Willie’s friends provided alibi that he couldn’t have been. The case went back and forth, but Willie’s lawyers were forced to give him a grim ultimatum: That he could plead down to a lesser charge or risk execution.

    To quote Willie:

    “When you are guilty, you are depending entirely on your legal rights; the maze of protections, legal maneuvers, and loopholes that can help you beat the trap. You have no qualms whatsoever about using them, the law says you have the right. But when you are innocent, you are always in a rage of indignation. You feel helpless and put upon. You are totally on the defensive. Constantly you have to fight back the desire to leap out and scream your innocence. You can’t believe this massive grinding machinery is doing this to you.”

    Willie & Eddie decided to hit the Ozone park bank. After much planning, they broke into the bank basement, with the intention of drilling up and into the safe from below, and then using welding torches to cut a whole in the side. But the plan was too complex. First, they had to build a wooden platform that would boost them up to the ceiling of the cellar. Then they had to drill through the concrete floor, which was a full 5 inches thick and much better made than Sutton had anticipated.

    It took them until 7:30 the next morning to get to the safe, by which time a pair of cops were taking a break in the lobby. They abandoned the job, leaving the welding torches behind.

    Eddie drove the getaway car, but he wasn’t very careful and lost control in the wet. He crashed the car into a truck. He exchanged details with the owner and moved on, but it wasn’t long before the crash came back to haunt them. Later that day, they were having lunch with Sutton’s mum (who he hadn’t been to visit in 5 years, which should give you a good idea of what kind of guy he was). They were interrupted by a cop, who was interested in the banged up car out front.

    “There was a hit and run last night” he said. “We doubt it’s you but can you come down to the station to clear it up?” Not wanting to upset Willie’s mum, they went down to the station house and gave over their details. Unbeknownst to the pair, the cops had already traced the welding equipment they left in the bank basement to the Acetylene gas vendor, who identified Eddie, who was now firmly connected to Sutton via the car crash. They were charged with burglary and grand larceny.

    Eddie was tried first. He opted to defend himself, using his impressive college education and public speaking skills. He was quickly convicted and given 10 years. Sutton opted for the more
    traditional approach of retaining a defence team. The prosecution presented a fake witness stating he had seen Willie fleeing the robbery, but his lawyer tore the witness apart on the stand, leaving the state with a flimsy case that relied on him being seen with Eddie later in the day. The jury came back hung, and the state offered Willie a misdemeanor charge to avoid a retrial. He turned it down.

    The retrial saw Willy face a different judge, and he got sentenced to 10 years in Sing Sing.

    Named after the nearby town of Ossining, Sing sing state penitentiary is pretty famous as a prison for hardened cons. It turns up constantly in 20th century gangster fiction. But in reality, Sing Sing was downright progressive compared to other prisons of the era.

    It was right near New York City, which made it easy for visitors. Packages from the outside came freely, and though the official prison food was terrible, the inmates had the run of the kitchen, allowing them to cook anything they wanted. There were education and rehabilitation programs. Some of the inmates were rich New York socialites that still had political pull (which ensured any problems were quickly fixed). The deputy warden was wildly corrupt, and he allowed gambling, trade, and even a little drinking, – for kickbacks of course.

    Sutton quickly made the right friends and settled in. He got a job in the garden, and was beginning to appreciate this tranquil life he had been given when he was transferred out of Sing Sing due to overcrowding.

    He & Eddie Wilson were sent Dannemora, which was basically a death camp.

    Right up on the Canadian border and surrounded by thick forest, Dannemora frequently got to 30 degrees below 0 in the winter. It was run by a giant, sadistic warden named Granger. Inmates weren’t even allowed to talk to each other. Guards would often murder prisoners on a whim by sending them to the isolation block and staging a suicide. There was an attached mental ward, where inmates were experimented on, beaten up, and forced to fight one another. The coal for the boilers was often stolen by the guards, there was a bed bug infestation, and no running water in the cells. The inmates showered for 2 minutes a week – 1 minute with hot water, and 1 with cold. Keep in mind: it was -30 outside. The best part: Dannemora is still an operational prison (though it’s been renovated, and is called the Clinton Correctional Facility now).

    There were jobs available for the inmates, but Willie was denied one by the warden when he refused to rat out a man who knifed another inmate. So he would just spend all day reading. Classic literature, chemistry, psychology, anything the correspondence course could get its hands on for him.

    Prisoners would escape from time to time – but there was no where to go. The nearest town was inhabited exclusively by guards, and the forests where nigh on impossible to navigate. Willie spent 3 years in that god forsaken place before he was sent up for parole, which, much to his shock and elation, he was granted.

    “It is incredible how that first glimpse of freedom can quicken the heartbeat and alter your perceptions. Suddenly, you become aware of the passage of time again.”

    Before his release date could come through though, the prison saw a massive riot. Lifelong inmates couldn’t take the mistreatment anymore, and organized to attack the guards during lunch.

    “It was the most awesome, frightening thing I have ever experienced. From one second to the next, they turned into a wild eyed, hate crazed mob. They were out to wreck, render asunder, to tear apart.”

    They smashed their way into the workshops and grabbed pipes, hammers, rods anything they could use as a blunt weapon. They poured oil and grease onto the ground and lit the buildings afire, before rushing out into the main yard and charging at the walls. They were met by a hail of machinegun fire from the outer towers. There was smoke everywhere, and the prisoners scrambled for what little cover they could find between the incoming bullets and the outgoing flames. Sutton pinned himself to a wall and watched as a friend was gunned down a few metres from his position. The army was called in to help quell the riot, and after 5 hours of grenades, gunfire, and fire hoses, the massacre ended with the surrender of the remaining holdouts.

    Officially, only 3 men died, but Sutton was sure he saw more than that gunned down, and the extreme brutality of the beatings the guards dished out to the surviving prisoners almost certainly resulted in further fatalities. Sutton took a beating or two as well, but his parole saved him. On release, the Warden told him “If you ever come back here, Sutton, you wont leave alive.”

    He was 28 on release and determined to go straight. His next conviction carried a mandatory 25 year sentence in New York state. He was sent to live in Brooklyn with his mother, he got a job doing landscape gardening, and starting dating a girl from the neighbourhood who he had been exchanging letters with. They got married, she fell pregnant, everything was going great, right up until the stock market crash of 1929. Sutton, like millions of other Americans, lost his job.

    It may seem inevitable that he would return to a life of crime, but to be fair, how else could a lower class ex con with little formal education afford to raise a family in the middle of the depression?

    He hunted down a new partner, and he picked Jack Bassett, a fellow inmate of his at Dannemorra. Sutton picked him because he considered him a very loyal, trustworthy guy, but it was still a terrible choice because Bassett was really dumb, and it was going to cause all sorts of problems.

    The plan was the same as the jewellry store robbery with the broken watch. Sutton would put on some sort of act, fool someone into letting him inside, then pull out a gun and rob the place. The first target was another jewellers, Rosenthal brothers.

    On the morning of the robbery, the porter, Mr.Lewis, arrived at 7:30am to open the place up. Willie watched him through the window, waited for the alarms to be shut off, then rang the front bell. Mr.Lewis opened the door to find a Sutton dressed as a mailman.

    “Telegram for Mr.Rosenthal, would you like to sign for it?” he said.

    Lewis very briefly dropped his guard, just long enough to take his hands off the door so he could hold the envelope to sign it. Sutton rammed the door open, held out his pistol, and told Lewis to get inside. Bassett, who was watching from over the street, ran over and shut the door.

    Lewis tried politely to reason them out of it, but Willie ordered him to stand at the window as though nothing was wrong, and one by one the rest of the bank employees entered the building. Bassett tied them up as they came in. The head salesman had the combination, so he was marched to the back and ordered to open the safe.

    After 15 minutes of fiddling around with the lock, including an attempt by Mr.Lewis to alert his boss via a phone call, they walked out of the safe room with 150,000$ in jewels. They flung on overcoats as disguises, then left the building, the burglar alarm ringing in their ears as they jogged up the street to the getaway car.

    The new system worked. Sutton was now confident he could be let in anywhere. They hit the Richmond Hill bank for 19,000$, the Converse Bank outside Boston, banks and jewellers throughout the five boroughs of New York. They expanded into Massachusetts and Pennsylvania on a regular basis. They used a police uniform so many times that the NYPD began checking their own ranks for a gang of rogue cops. Banks started devising warning systems for the other employees – small clues like an upturned calender in the window – so that if the first person to come in was taken hostage, the others would know to call the police. It didn’t work – Sutton’s research and preparation was so thorough he picked up on the tactic right away.

    He worked hard on his disguises. He plucked eyebrows, dyed his hair, shaved his head, put on and took off weight; the papers gave him the nickname – Willie the actor.

    He was downright gentlemanly during every robbery, using the eloquence and sophistication he picked up during his time on Broadway. One of his victims stated: “Being robbed by him was like going to the movies, only the usher had a gun.”

    Irrespective, all of these robberies were armed robberies,even though a shot was never fired. The idea of actually pulling the trigger bothered Willie deeply. Quote:

    You pull that trigger the first time, and maybe it would become easier the second.

    He used a pistol most of the time, but if he could hide it on approach to the bank, he preferred to use a Tommy Gun. It was just more intimidating.

    The only time they ran into any trouble was when a teenager slipped out of Bassets control and ran out the door. The pair abandoned the job immediately and ran for the car, but the car wouldn’t start. The kid came running down the street with a cop in tow as Basset desperately turned the car over. Sutton had a brainwave. He got out of the car, casually leaned against the window and calmly watched the cop approach. The cop became puzzled, and despite the kid shouting and pointing at Sutton , slowed his approach to a crawl.

    The second the car started Sutton dove in through the window and they skidded off, leaving the officer no time to unholster his gun. It was the only time they ever had to speed away from a bank.

    Sutton used the money to buy a big house in a rich suburb, and told his wife all the money was coming from his realty business. Sutton says that she probably figured it out, but she played the role of a house wife, picking him up from the station every day.

    Basset bought expensive suits and starting keeping girlfriends in a number of different apartments throughout the city, blowing heaps of money in exuberant displays that bothered Sutton. He was not keeping a low profile at all. Willie had to begin loaning Basset money just to keep the partnership running, and before long, Basset’s wife Kitty realized something was up.

    One afternoon, she met Sutton for lunch. She knew Basset was cheating on her with at least one other woman. Sutton fed her a convoluted story about the other woman being a criminal associate, but he knew that wouldn’t hold for long. He tracked Basset down and insisted that he clean up his home life.

    “Jack, if we ever take a fall we have to get 30 years as second offenders. Do you realize the situation you’re causing here? If Kitty should go haywire, we’re cooked.”

    But Jack Basset was pretty stupid. Jack told Sutton that he dumped his girlfriends, but instead he hid his favourite one in a different apartment. Kitty Basset found out the full details soon after, and in a fit of rage turned the pair of them into the cops. Sutton evaded detectives for a full week, going so far as to knock a pair of them down during a foot chase down a flight of stairs. They got him by getting Kitty, whom he still trusted, to set up a meeting with him. The cops ambushed him over coffee and cake.

    To make matters worse, Basset completely spilled his guts. This man that Willie relied on for the sole reason that he felt he was loyal to his friend, betrayed him completely. They had robbed over 60 banks.

    Sutton was taken into custody, and over a hundred people were brought in to view him a police line up. His disguises had been so good that only 1 man was able to correctly identify him. Mr.Lewis, the steely nerved Porter from Rosenthal’s jewellers, picked him out in a heartbeat.

    Then they took him downstairs and beat the crap out of him with phonebooks. They were mostly interested in Suttons underworld contacts, primarily mob boss Dutch Schultz, who Sutton sold stolen goods to. Willie hated Schultz, but wouldn’t rat on him. It was both against his code of conduct and very risky for him personally – Schultz could have had him murdered in prison quite easily.

    In response to his fortitude, the detectives took him down into a sub basement, stripped him naked, tied him down to a table, and thoroughly beat him with rubber hoses.

    “I was one solid contusion, front and back. A slab of quivering pain.”

    Then they flipped him over and did the other side.

    It was 4 days before he was allowed to see anyone, including a doctor. The cops arrested his pregnant wife, who turned over all the money she could find to them.

    Dutch Schultz sent a corrupt ex judge, Arthur Vitale, to represent Sutton. The problem was Vitale. He was an eminent trial lawyer, but his corrupt behaviour from his time as a judge made him hated by the legal establishment, and Willie could not get a very fair hearing with him as his lawyer. The judge overruled everything he had to say.

    Willie was convicted, and as this was his second felony, he was given the mandatory minimum of 30 years. He was back in prison after just 15 months of freedom. It was 1930, and he was just 29 years old.

    ACT 2

    “There’s a thrill that comes from breaking out of jail, after years of the most meticulous planning, with everybody watching, against all the odds, that is like nothing else in the world.”

    Sing Sing had been completely rebuilt since Willie’s last stay. The old cellblock had been levelled and the hilly ground it had been built on was levelled off. It was said to be escape proof. Higher, thicker walls, more barbed wire, and stronger steel bars that allegedly couldn’t be cut through.

    First, he had to visit the warden and tell him that he had to stay at Sing Sing to appeal his sentence. Willie had broken probation with his conviction, and now had to serve the rest of his first conviction, which meant being returned to Dannemorra, which was a death sentence.

    His first attempt was an underground tunnel. During his outdoors time in the yard, Willie found an opening to a cellar, which led to a piece of pipe that was under construction. A new powerplant for the prison being built outside the walls, and this pipe must have been where the cabling was going to go.

    Once he figured out he fit down the hole, he decided it was a great escape option. He just needed to find out when the breakthrough was going to happen. But he was beaten to the punch. 4 prisoners escaped through the pipe into the new power station. They were caught trying to steal a rowboat just a few hours later.

    His second plan involved a pair of short ladders in the mess hall that were often left unattended, and the news that the southern tower was unmanned at night. The guards figured it didn’t matter, because the cells were escape proof.

    Sutton got himself a few small hacksaw blades and was able to very quietly work away at the bars over several nights. The guards didn’t notice the cuts, all the way down the bottom of the bars, and they had no need to check, because they all knew the bars were impossible to cut anyway.

    Getting out of his cell was easy, but getting out the prison and not getting caught immediately as he tried to flee – that was the hard part. There were 7 doors he had to get through before he could access the yard, and then he would have to strap the ladders together, climb the wall, scale down the other side without killing himself, and meet a contact on the other side who could drive a getaway car.

    He made wax impressions of the first 3 doors (which were little more than house locks). This took him months, because the doors were usually guarded during the day. The next three were iron gates, but he could pick those very easily with simple tools. The last one required one of the prison trustees (a prisoner with special privileges) to sneak into the guard room and make a wax impression of the key.

    He had to take another man, Egen, with him. He didn’t really want to, because it complicated the plan, but Egen was the one getting him the hacksaws and lockpicks, so Willie obliged. One night, around 11pm, the two removed the cut bars, carefully replaced them, and tiptoed down the cell block. They grabbed the ladders from the mess, lashed them together, and made their way to the locked doors.

    (Click sounds)








    They were out in the yard. There were searchlights everywhere, so they ran the ladder along the outer walls, and quietly as they could, made their way to the southern tower. Willie did so with gritted teeth, bracing himself for a hail of machine gun tower from the other towers that were manned. They hoisted up the rickety ladder, scaled it and found…

    An empty tower, with a convenient rope left hanging all the way to the ground. The guards used it to haul up snacks when they were too lazy to climb down. The pair ab seiled down the outer wall, and ran to the nearest road, where Sutton’s swife was waiting in a brand new Buick. They clambered in. She floored it, and drive them back to New York City via country backroads with the headlights off the whole way. She had spent months practising the route at night until she knew it like the back of her hand.

    It was the perfect escape. Time in custody: 25 months.

    Sutton ended his marriage shortly after escaping. He knew his wife would eventually get arrested, and he couldn’t risk his daughter becoming an orphan to a pair of convicts, so he left her.

    He then contacted Bo Weinberg, a confidant of mob boss Dutch Schultz. He gave Willie 1500$ and an unlimited line of credit. They then visited Egen’s brother down at the docks, who promptly abused Egen and told Sutton not to work with him under any circumstances. Egen was a hopeless drunk and totally unreliable.

    He met with Eddie Wilson, who was now out on parole, and the three of them attempted a bank job in the Bronx. It failed because Egen got blind drunk instead of showing up to the job.

    Sutton skipped New York for Philadelphia., But before he left, he couldn’t resist once last dig at the NYPD. He robbed the Corn Exchange bank on 110th and Broadway, which is 3 blocks west of central park, right in the heart of Manhattan itself. He walked across the road, in the middle of the day, dressed as a cop. He gave a friendly wave to the traffic police on the corner, stepped inside the bank, rounded up the employees, flirted with a few of the tellers while Eddie emptied the safe, and then skipped back outside to catch the Subway to Queens. Willie remembered it as one of the most fun robberies he ever committed.

    Sutton & Wilson got another partner named Perlango, and began knocking over banks in Phyllie. They hit about 20 before security measures got too good for them to deal with, including one occasion where a woman outside the bank saw Sutton disarm the guard through a window, forcing them to abort..

    They started hitting the surrounding towns, like Scranton, instead. But the bank job they had to abort annoyed Sutton. He had to go back and have another go at it. The new system the bank was employing was to have the guard lock the door after each employee arrived, including himself. This way Sutton couldn’t use his usual plan.

    Instead, they cut a hole in the ceiling, rappelled down a rope, disabled the alarm, and waited until the guard showed up. The moment the guard locked the door, he turned around to see Sutton with his feet up on the managers desk holding a pistol.

    Quote: “The way his eyes bugged out, I thought he was going to have a heart attack.”

    The bank manager was late that day, and by the time Sutton had finished with the safe, a crowd of customers had assembled. “Just a minute! The bank will open shortly” Sutton told them, before walking right out the front door.

    Once again though, his choice of partner would prove to be Willie’s undoing. The new guy, Perlango, had grown up poor and didn’t handle money well. He was still living in the eastern slums of New York where he had grown up, except now he had nice suits and a shiny new cadillac. The police noticed, tailed him, and caught Eddie picking him up. Eddie spotted the tail and tried to shake them off, but he ran into traffic and was gunned down by the cops. He lived, but was permanently disabled.

    Perlango confessed to everything, including where Sutton was living. On February 6th, 1935, the Philadelphia and New York police department (who sent a captain and 6 detectives for the occasion), stormed Willie’s apartment in a joint operation. In a swift trial, in which Sutton was appointed no council, he was given 25 to 50 years in Eastern State Penn.

    Opened in 1829, Eastern State Penn was dank, cold and miserable, the fatality rate was
    high, and prisoners were kept in permanent solitary confinement.

    By Sutton’s time though, Eastern State Penn had improved dramatically. They had a shop program, a place where prisoners could run their own craft market, and it was right in the middle of Philadelphia

    The warden knew of Sutton’s skill in escaping, and was taking no chances. He spent his first year there on an isolation ward, and another 6 months before he was allowed into the yard with the other prisoners. Even then, he was still banned from the tool shop.

    Instead, he became a secretary to the prison psychiatrist. He got it by practicing typing 16 hours a day in his cell block during isolation, during which time he wasn’t even given a real typewriter, just a piece of paper with a picture of typewriter keys on it. It was a quiet, unassuming job, which gave him a lot of scope to talk to the right people and keep his eye out for an opportunity for an escape. In the meantime, he studied. He took refresher courses in English, studied abnormal psychology, history, geography, economics, politics, classic philosophy, whatever he could.

    His first escape attempt came when one his friends, Adam the Plumber found the main sewer. He was sure that there would be an exit grate to the main city sewer system in a large basin under the main tower. But it could it used to escape? Adam figured there would be some sort of basin gate that you could get into the main city sewer system from, but Sutton would need a way to prop it open.

    They a few weeks later during a guard switch, Adam dug out the earth surrounding the manhole. They raised the cover, and Sutton, butt naked, lowered himself into sewer. He had a torch and some metal rods strapped for the gate. He had to lie on his belly and wriggle along to move. The pipe was filled with giant cockroaches, and there was a thick green slime on the walls from years of human waste flowing through. Every now and then, a toilet would flush.

    The pipe got deeper as he went, along with the water level. It was up to his chest by the time he got to the basin. There was solid waste everywhere, and not just feces. Bandages, wet wipes, and general medical waste. He pulled out the rods, assembled them into one long pole and poked around for the basin door.

    But there was nothing. The basin was huge. He tried to swim around looking for it, but he wasn’t in water. It was a molasses like well of human waste. He almost drowned trying to get himself back upright, bursting through the surface and gulping in what little air was there.

    Then his torch battery died.

    He had to get back to Adam, and fast, with no sense of direction. The guards would eventually move him along, and Willie needed him to pry the manhole cover open. In total darkness, total panic, and naked and covered in shit, Willie fumbled around in the dark until he stumbled on roughly the spot Adam was waiting, and pounded on the roof of the pipe like madman. The grate lifted and daylight poured in, revealing Adam’s beaming face.

    They abandoned the sewer plan.

    His next attempt involved the weather. He was able to climb up onto the window sill of his cell at night and look down at the yard. There was a changing of the guard at midnight, and Philadelphia was sometimes beset by heavy fog in the Summer. It was so heavy, that you couldn’t see the walls. If he could get just get out of his cell on the right night, he was a free man.

    He was still being watched very closely, and there was always a bed check 5 minutes after midnight. The guards made certain to shine a torch on Willie to make certain he was still there. He decided he needed three things: A rope to climb down, a hook to climb the wall, and a really good dummy of himself.

    He built a secret compartment in the floor of his cell, stowed a rope and a hook in there. He made a plaster cast of his face using some old construction putty. He painted it using leftovers given to him by the guys in the craft market. He saved his hair every time he got a haircut to give it a perfect wig. He was so happy with the cast, he made one of his hands too, just to make it that extra bit convincing. After a year of preparation, the night finally came. A heavy fog rolled in. He got out of bed, laid down the dummy, unbolted the window frame and…..

    There was a scuffle in down in the yard. Some other prisoners had the same plan, but mistimed the guard change and went too early,. Searchlights opened up, alarms went off, gates were locked down and Sutton went back to bed.

    The next morning, they found his secret compartment, and he was thrown into solitary for 6 months. These escape attempts did not occur overnight. By the time he was released back into Gen Pop, he had been in Eastern State for 6 years.

    The next attempt was the most elaborate yet. Willie and 6 other prisoners hauled a thick granite slab out of one of their cells, replaced it with a dummy to disguise the entrance, and during yardtime, they would raise it up, lower themselves down, and dig out a tunnel.

    It would be a full 95 feet and extend all the way under yard. Now, building a tunnel at the best of times is a difficult affair. There are cave ins, floods, you might need to blast rock out of the way, and even if you can excavate the space, you still need to get rid of the dirt.

    They don’t have good equipment. They have spoons, bevels, and a shovel with almost no handle. To begin with, they get rid of the dirt a handful at a time by stuffing it into their pockets, walking into the yard, and sifting into the dirt with their feet. Later on, they route the tunnel over the main sewer and just dump it all in there.

    Only one man at a time could dig. It was slow, dangerous work crawling on their bellies. There wasn’t much wood for support, so they were are at constant risk of cave ins. They had a jury rigged extension cord system providing light. One afternoon they hit a big pocket of water, which flooded the tunnel. The men had to strip down to their boxers to dig. They were under the outer wall, but it was fifteen feet thick, and as they continued, the foot of air they had became an inch. They dug underwater with their lips sucking at the ceiling. They cleared the wall, dug up, and came across the first signs of grass roots..

    They decided that when they escaped, they would all go at once. It was very lucky that they would escape right into the middle of a major city. One Monday morning, 12 men in total crawled through the mud, lined up head to toe, and escaped Eastern State Penitentiary. Only trouble was, they popped right under the feet of two passing police officers on their regular morning patrol.

    Sutton and two police were stunned. The cops couldn’t believe the fountain of convicts pouring out of the ground in front of them. When they finally came to their senses, they decided to shoot at Sutton, who promptly bolted off down the street.

    He and 11 others were quickly rounded up and returned to prison. The warden was furious, and threatened to shoot Willie on the spot. Instead, he just threw the lot of them into the hole for a few weeks. They were cold cylindrical steel cells only accessible by a grill in the roof. Rations consisted of two cups of water a day and 6 pieces of white bread. Willie could barely stand by the time he was moved to the isolation block. The guards would occasionally drop cigarettes through the grills as a compassionate gesture.

    They were taken before a court, without proper representation or planning. Sutton protested at the unconstitutionality of the proceeding, but all 12 were convicted of jail breaking immediately. Sutton got 10 to 20 years extra tacked onto his sentence because he was deemed to be the ringleader.

    He and 5 of the other escapees were transferred out of Eastern State, and sent to Holmsberg, an allegedly impregnable prison that hadn’t had a single escapee since it was built in 1894.

    Sutton broke out in 16 months.

    Holmsburg was the same design as Eastern State, but it had bigger walls and was miles out of the city. It was run by a medical doctor rather than a traditional warden, but he ran it brutally. There had been an attempt to break out the previous year, but 5 out of 6 of the escapees were gunned down in the gatehouse yard. The walls were heavily defended by machine guns.

    Sutton and his friends were placed in the isolation block. They were never allowed out, not even for meals. There was a small handball court behind a heavy wall, sectioned off from the rest of the prison by a heavy steel door. A single guard delivered their meals twice a day.

    There were no shops or industry at Holmsburg. The only way a prisoner could make money was to volunteer for cosmetic experiments. Willie wasn’t even allowed to leave his cell block for medical reasons. One day, he was taken to the prison hospital with a terrible fever. The warden sent him back to his cell, against doctors wishes. His orders were “If he’s going to die, he’s going to die in his cell”. His nurse was left an instruction to not bother calling the doctor for Sutton again, unless he was also planning on calling a priest.

    Willie remained in terrible health for about 2 months. He was nearly 50. A severe flu with this sort of medical aid could have easily killed him. The nurse, an imprisoned bank robber himself, could see that Sutton would not survive Holmsburg, so he told Sutton about the two ladders in the cellar of the isolation block that could be strapped together. They were long enough to climb the outer wall.

    Sutton was recycling his failed Eastern Penn escape plan. He would wait til heavy weather (in this case a blizzard, rather than a fog) and climb the walls in the confusion. There was no change of watch that he knew about, so he needed an added detail to confuse the patrols long enough to get him over the wall. They still needed to get through that heavy steel door, as well as past the guards at the cell block hub. But when you’re in prison for years at a time, you’ve got very little else to think about.

    There were 8 guards and a captain in the hub of the prison at night, and they carried no guns as a security measure. A prisoner couldn’t steal your gun if you didn’t have one. And that heavy steel door at the end of the cell block, it was so heavy that you couldn’t see into the cell block at all from the other side, leaving a large blindspot on the hinge side of the door. All that security was beginning to work against itself.

    But Sutton would need a weapon. There was simply no way for the 6 of them to overpower 9 men. The answer came from the 6th man in the isolation block, who came and went everyday. Langy the Rat.

    Langy was in a gang. He got arrested, and he ratted on everyone else to get a reduced sentence. He was hated by all the other inmates, and was housed in the iso block not as punishment, but as protection. He was given a job as a painter, and was allowed to freely roam the prison. He was extremely lonely and isolated, something Sutton exploited to a tee.

    Despite copping hell from it from the other guys on the block, Sutton befriended Langy. He did such a good job of convincing Langy they were friends, that Langy got Sutton a pistol and some hacksaw blades.

    The other guys were stunned, and refused to take action. They were sure it was a set up. That at any moment a wall of guards were going to come rushing into Willie’s cell, and use it as a pretense to beat him to death. But after a week, it became pretty clear that Sutton had the only gun in the prison. On the 10th of Feburary, a snowstorm arrived, and the men broke out of their cells and gathered behind the door.

    The guard came around for the hourly check, the 6 of them knocked him down, rushed the inner hub with the pistol and took everyone hostage. They cuffed the guards and brought them down through B Block, where they picked up two short ladders, several lengths of rope and a handy hook to affix to the top of the wall. They locked 5 of the guards in the utility closet, but not before stealing their uniforms, and entered the gatehouse yard with the captain and two deputies.

    It was freezing. Several inches of snow had already settled on the ground. Sutton ordered the deputies to make their way to the wall, and lower the ladder against it. The guards on the wall noticed this, and challenged the group. Sutton called out that they were an emergency repair crew, but the guys on the wall didn’t believe him and they started shooting.

    Everyone hit the deck, and Sutton jabbed the pistol into the captains stomach. This time the captain called out that they were conducting repairs. Recognizing his voice, the guards stopped firing, and the prisoners were able to prop their ladder against the wall, climb it, and scale down the other side. The captain was too scared to say anything, because in the darkness, he couldn’t tell if the man with the pistol was still with him inside the walls.

    They were free.

    Sutton and his men happened upon a milk truck setting out for its morning run. They hijacked it back to Philadelphia, and paid for a few bottles of milk with a spare 5 dollar bill. They abandoned it in an alleyway, and made their way to the safehouse, where they got new clothes and some money.

    The cops caught up with them shortly after. Gunfire was exchanged, and the 6 men scattered. Sutton jumped the fences of a few private houses before shaking them off. He was in the middle of Philadelphia, in winter, with a thin jacket, no money, and no connections. He hid out until the following afternoon. The newspapers were filled with news of the escape. 4 of them had already been apprehended, and Sutton didn’t plan on joining them. He hitchhiked to Princeton on the way back to New York.

    He went to see an old associate named Tommy Kling. He gave Sutton 500$ and a job offer, but Sutton wanted to lay low a while. He instead took a job up country as a nurse at an old folks home. It was perfect for him. No one would dream of looking for him there.

    But it became much more to him than just a hiding spot. Willie would stay for a full two and a half years. He came to regard it was one of the most fulfilling experiences of his life. It was a home for the destitute elderly. They were poets and artists that never quite made it, finance people that had lost everything in the crash, but they were mostly just parents abandoned by their children. In other words, a regular old folks home.

    Quote: “It gives you great insight into life itself to watch it ebbing out of a fellow human being.”

    Nevertheless, Sutton was Sutton. He, Tommy Kling and a 3rd man, Venuta, began pulling jobs around New York state. He would never stay in the city, and laid low at the old folks home between jobs. He started dating one of the head nurses, someone Sutton described as “a woman of boundless warmth and compassion for those she cared for”.

    Sutton had to quit his job when one of the other nurses joked about him being Willie Sutton, and went to live with his girlfriend at her townhouse. He stayed there for 9 months. He treasured every minute, because he knew he was on borrowed time. Eventually, she’d see his photo in the paper.

    It was a job that Sutton didn’t pull that exposed him. A gang pulled an aggressive frontal assault on a bank using Halloween masks, and the papers blamed the Sutton gang, putting his picture on the front page. When she confronted him, he left her 700$, abandoned his car, and bussed his way back to Manhattan.

    Three days later, his girlfriend was arrested and taken to a nearby women’s remand center as both a witness and suspect.

    He continued working, but as always, his partner started causing trouble. Tommy Kling had started speculating in property around town with the help of a shady lawyer that was stealing his money. Willie and Kling even had to go over to the man’s house and put a gun to his head. He was also living with a sex worker that too much about their operation, including where Sutton lived. At the same time, Sutton was working on a new, very complicated robbery on a large midtown bank. He was under a lot of stress.

    Kling didn’t have a car, his money was all tied up in these bad investments. Willie was headed over to Kling’s one day to pick him up when Willie’s car failed to start. Dead battery. So he headed to the mechanics for a new one. Mechanic wasn’t in. So he caught the subway to see Kling, who insisted that Willie go get the car, because the lawyer was promising he’d finally have the money. So Willie rushed back to the subway, just made the train, got back to the car, made his way back to the mechanic, buys the battery…..

    …And ran into two detectives. He’d been so stressed he hadn’t noticed that some guy recognized him on the train. To make matters worse, Kling’s girlfriend would lead detectives to both Kling and Willie’s apartment, creating an open and shut case for the prosecution. Once again, he was babysitting the wrong partner.

    His arrest was a circus. The NYPD paraded him in front of the press, declaring an end to the longest manhunt in New York history. He was placed under very heavy guard, and wasn’t allowed anything in his cell that could be used to escape. They even took his belt buckle, shoes, and toothbrush.

    Outside the jail, Sutton was a celebrity. People cheered when his picture was shown in theatres, and crowds would gather for his arraignment, chanting his name and egging him on to escape. Sutton had never once hurt anyone, and the public, who had just come out the great depression, hated the banks. He was a folk hero.

    But the man himself didn’t get it. “Not in my wildest dreams had I ever looked upon bank robbery as a revolutionary act., and busting out of jail had no social significance whatsoever. Hell, I was a professional thief. I wasn’t trying to make the world better for anyone but myself.”

    While awaiting trial, his daughter came to visit him. She told him she was so happy to finally learn what he looked like, and that he was a grandfather to an 18 month old boy. His ex wife had married a burly engineer. His own mother was still alive, at the same house in Brooklyn, spending her time fighting off the journalists that wanted a photo.

    At trial, he was found guilty and sentenced to 45 years in Attica. 15 for the Corn Exchange Bank, and 30 for a firearm possession in violation of his parole. The judge lamented that he couldn’t give Sutton a death sentence. His total, cumulative sentence was now a minimum of 132 years.

    He was 52 years old, and could no longer jump, run, dig or climb a wall like he used to.

    Attica was a different sort of prison. It wasn’t brutal like Dannemorra, or industrious like Penn State, or deregulated like Sing Sing. It used a weird kind of bureaucratic excessiveness to wear down the prisoners. The guards handed down minor punishments for just about everything.

    Life there was fairly uneventful. Sutton was placed in isolation on and off, he helped calm a potential prison riot in 1965, and experienced some drama when the prison tried to desegregate during the civil rights movement.

    He wasn’t allowed to have a job. He wasn’t allowed to talk to many of the other inmates, he wasn’t even allowed to go to the prison commissary because it was considered to close to the front gate. In 1966, he had a chance to escape. Some of the other inmates had a complicated plan involving distracting guards and prison trucks, but Sutton turned them down. After all his years on the run, he’d come to realize that life as a fugitive was just another form of prison.

    Besides, he had found another way out. He was going to fulfill boyhood dream. He was going to become a lawyer.


    In 1953, there had been a landmark court case. Brown v. Allen. It involved an African American man on death row appealing to the supreme court to have his conviction thrown out on the basis that his trial had been unfair. The supreme court found against him and he was subsequently executed, but the important part was that the supreme court had bothered to hear his case.

    Usually, these cases would get kicked around local and state courts, who would invariably find in favor of the state, and the prisoner stayed imprisoned. Brown v Allen set a precedent for supreme court challenges, and a number of very important decisions came down that ruled that many trials being conducted at the state level were thoroughly unconstitutional, and thus, could be overturned.

    Sutton had a nest of convictions to have thrown out, but in many ways, that worked in his favor. Several of his convictions relied on prior convictions, such as the mandatory minimum 25 years he got when he was arrested after release from Dannemorra. Knock out one conviction, and the rest would follow. He partnered with Katherine Bitses, god fearing trial attorney who had opened a community legal practice in Queens.

    Sutton wasn’t sure if he would live to see his convictions overturned. That same year, he had to have major surgery to correct clogged arteries, which had essentially paralyzed him from the waiste down. The surgeon insisted he come back for subsequent operations, but between his need to appear in court and the reluctance of prison authorities to release him for medical reasons, he had to take the risk that he wouldn’t die of a heart attack before they released him.

    In 1968, they begun by getting his conviction as a 4th offender from his 1934 Philadelphia arrest thrown out, on the grounds he wasn’t given any counsel. It was successful, and the conviction was set aside. This meant that he could have the life sentences on gun charges from from his 1952 New York arrest set aside for resentencing, because that sentence was based partly on his 4th offender conviction.

    Bitses then spent a month being intentionally messed about the Philadelpia District Attorney, who lost paperwork, refiled it, told her at the last minute that she couldn’t file papers there anyway because she wasn’t a member of the state bar (forcing her to get someone else to do it for her), and when Willie finally got his day in court, they changed the venue at the last second as a final insult. In court the district attorney announced he had slapped a number of new detainers on Willie (a detainer is to hold a prisoner in a given jurisdiction). The motion to remove the detainers was denied, and Willie would have to wait in Philadelphia for the appeal to the Superior court. In the meantime, the court in New York resentenced him on the gun charge – 1 year suspended, down from the original 30.

    10 months later, his appeal was denied at the superior court, which allowed him access to a state supreme court appeal. The Supreme Court of Pennsylvania found in his favor. They said the state had failed repeatedly to provide Willie adequate council for both his 1934 conviction and the Penn State escape, and that they’d had a full 17 years to do so. The court quashed both those convictions. The state had the right to further appeals, but there was an election coming up, and it did the governor good to let a sick old man with a big fanbase out of prison. Plus, the state was worried that a high profile case like this could encourage a flood of petitions from other inmates. If Willie was willing to cop a misdemeanor charge with time served on the Holmsburg escape, they wouldn’t fight the other two convictions. This freed him from Pennsylvania.

    Back in New York, he was resentenced for the Corn Exchange bank robbery, the one near Central park. He got 15 to 20 years. He’d been in Attica for 17 years at this point which meant he was due for a parole hearing. On ruling, the judge commented that “I cannot hold any brief for your client because the probation report indicates he has probably the worst criminal record of any man who has ever appeared before me in 45 years in the administration of justice.” However, the judge was swayed not only by time served, but also Sutton’s ill health, and argued that on compassionate grounds, he would be freed.

    In closing, the judge said:

    “There is only one thing they I want to add. They all speak of his tremendous ability. I sum it up differently. He began to believe his own publicity. That is the disease he suffered from.The fact

    “There is only one thing they I want to add. They all speak of his tremendous ability. I sum it up differently. He began to believe his own publicity. That is the disease he suffered from.The fact that he was not right is indicated by the number of times he was caught, and the number of years he has been in prison. But he was glamorized. That is the sad state. He was glamorized the entire time.”

    The parole board initially denied Willie’s release, and it looked as though he would have to wait another 2 years. In response, Bitses went on a publicity campaign. She wrote an open letter to the Governor, went on talk shows and got support from The New York Post.

    On Christmas Eve 1969, Sutton was handed a cheque and a suit, and released to a snow lined New York street. The governor, unable to pressure the parole board, eventually instructed the prison authorities to more or less just release him. No one would stop them. After 20 months of bitter legal wrangling, the state released him with a resigned shrug.

    Sutton lived out his days iin Florida. He did a few talk shows. Wrote not one, but two autobiographies, and in a fitting piece of final irony, in 1976 he made an ad for a bank advertising a new kind of Mastercard. Here’s the audio:

    On the second of November, 1980, he died of Emphysema. He broke out of prison 3 times, stole an estimated 2 million dollars, and spent more than half of his life behind bars.

    So who was Willie? And what drove him? Well, remember his time at Penn State, when he worked with the prison psychiatrist? Sutton once asked him if he thought he could be rehabilitated, and this is what the doctor said:

    “I think that banks will always present such a challenge to you that I have serious doubts you wouldn’t try and rob one the moment you were out on the streets.”

    And by Sutton’s own admission, the doc was right.

    “Why did I rob banks? Because I enjoyed it. I loved it. I was more alive when I was inside a bank, robbing it, than at any other time in my life. I enjoyed everything about it so much that one or two weeks later I’d be out looking for the next job. To me the money was chips, that’s all. The winnings. Nothing more.”

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