After 10 years behind bars, John Dillinger went on a year-long bank-robbing spree that captured America’s imagination.
The bank robber and gangster John Dillinger didn’t live a long life, but he spent almost all of his 31 years in some kind of trouble.
He quickly gained notoriety as one of America’s leading celebrity criminals, becoming a legendary media character who commanded the entire country’s attention.
In the months he spent terrorizing the American Midwest, John Dillinger helped reshape federal law enforcement and changed the way interstate crimes are investigated for nearly a century to come.
But like most famous criminals, John Dillinger’s death was as violent as his dealings.
John Dillinger: A Troubled Boy
John Dillinger was born in Indianapolis in 1903. His parents already had a 14-year-old daughter, Audrey, and his mother passed away in 1907, when John was three.
Back then, it was customary for widowed men to find alternative arrangements for their children, so Dillinger’s father quickly married off Audrey and sent John to live with the newlyweds.
But a few years later, after his father remarried and Audrey’s family grew too big to manage, John moved back in with his dad.
By this point, the young Dillinger was already a handful. He bullied kids at school and became the lead of a neighborhood gang, with whom he stole coal from the Pennsylvania Railroad. And thus began his first run-in with the law: When some of the housewives he sold coal to ratted out him and his co-conspirators, Dillinger got a talking to from a local judge.
And a talking to was all he got — no punishment, not even an actual slap on the wrist. The judge might have thought the lecture was enough to set him straight.
Boy was he wrong.
Dillinger’s Run-In With The Law
John Dillinger dropped out of school as a teenager and worked at a machine shop in Indianapolis, spending his spare time shoplifting and drinking. Afraid the city was corrupting his boy, Dillinger’s father moved the family to rural Mooresville, Indiana.
The move to farm country came too late for Dillinger. By this point, he was molded into a young man who always seemed to be looking for trouble. He fell in love with a young woman — Frances Thornton — but her stepfather’s disapproval brought their affair to an end.
In 1923, at age 19, he boosted a car in Mooresville and took a joy ride around Indianapolis. When the police were hot on his trail, he escaped capture on foot and enlisted in the Navy to avoid prosecution.
Predictably, he had a problem with maintaining discipline and following orders, so just a few months after joining, he deserted while his ship was docked at Boston Harbor. He ultimately received a dishonorable discharge and went back home to Indiana.
Cleaning Up The Act And Marrying
Back in Mooresville, 20-year-old John Dillinger bounced around from job to job and from woman to woman. His father had become a member of the local clergy, and the family was getting fairly well-known around town.
He met 16-year-old Beryl Hovious and the two became attached, marrying on April 12, 1924.
Despite appearances, however, Dillinger had not changed his ways. When it became clear he couldn’t support his wife, Dillinger turned to the only thing he knew: crime.
John Dillinger’s Prison Stint
Not long after his wedding day, Dillinger and an associate, Ed Singleton, waited behind a church. They knew that Frank Morgan, an old grocery store owner in town, walked the same route home every night.
As Dillinger later recounted, “When [Morgan] came along I jumped out from behind the building and hit him twice on the head with a bolt which I had wrapped up in a handkerchief. He then turned and grabbed a revolver which I had in my hand. The gun was discharged when I jerked it away from him, the bullet entering the ground. We then ran.”
The Mooresville Times’s account of the story mirrored Dillinger’s — with the added detail that Morgan’s wounds required 11 stitches.
Dillinger’s father talked him into confessing, pleading guilty, and asking for leniency. Instead, the court threw the book at him.
Ten years later, Indiana Gov. Paul V. McNutt lamented Dillinger’s harsh sentence: “The judge and the prosecutor took him out and assured him if he would tell certain things they would let him off with a lighter sentence. They didn’t keep their word. They gave Dillinger 10 to 20 years while his partner in crime, Edgar Singleton, got two to 14 years and was released at the end of two years. This made a criminal out of John Dillinger.”
Years later, Dillinger wrote his father: “I know I have been a big disappointment to you but I guess I did too much time, for where I went in a carefree boy, I came out bitter toward everything in general….If I had gotten off more leniently when I made my first mistake this would never have happened.”
To add insult to injury, Dillinger’s first prison physical included a diagnosis of gonorrhea.
He wound up serving nine and a half years. In 1929, five years into his sentence, John Dillinger’s wife Beryl got a divorce, unable to handle the separation.
Dillinger Tastes Freedom
Did Dillinger’s length sentence really make him a criminal? Well, before his incarceration Dillinger committed a smattering of one-off petty crimes; after nine and a half years milling with convicts in the Indiana State Prison system, he promptly committed a string of high-stakes, high-profile bank robberies.
Resenting society and embittered by the harshness of his sentence, John Dillinger got serious about learning the criminal trade. Surrounded by several of Indiana’s worst bank robbers and strong-arm men, Dillinger spent most of his 20s learning as much as he could about organizing stick-ups and evading the law.
Instead of acting like a loudmouth, Dillinger minded his manners and picked the brains of several notable criminals, including the likes of Harry Pierpont, Charles Makley, Russell Clark, and Homer Van Meter.
But then came a shift. In the early 1930s, the Great Depression stretched the Indiana state penal system thin. Funding cuts were exasperated by a doubling of the prison population, after families who’d lost everything began stealing and pilfering out of desperation. In 1933, a new parole board convened, and it was looking to free more inmates than before.
Dillinger wrote his sister, Audrey, and asked her and their father to help Johnnie plead his case for early release. The family obliged and circulated a petition that got 188 signatures. On May 10, 1933, with the blessing of Gov. McNutt, 29-year-old John Dillinger finally got paroled.
Meanwhile, the Great Depression was still in full force, and work of any kind was almost impossible to find, even for the most dedicated and hard-working men. Unfortunately, Dillinger was neither of those things.
John Dillinger: The Bank Robber
At Dillinger’s parole hearing, he vowed to return to his family’s farm and work the land after his release. Needless to say, that didn’t happen.
Dillinger immediately turned to the crime he learned so much about in prison: bank robberies. Just a month after returning home, he gathered a crew of men who had been recommended to him in prison — Paul “Lefty” Parker, William Shaw, and Shaw’s friend Noble Claycomb — and robbed $10,000 from the New Carlisle National Bank in Ohio. They camped out in the bank overnight, tied up two employees the next morning, and forced a third employee to open the safe for them.
Rather than coasting on that score, which was almost $200,000 in 2019 dollars, Dillinger and his gang moved onto another bank — this time Bluffton. This bank had been robbed before, however, and so the team got away with less loot — only $2,000 — and had to fire shots to escape through the windows. “The bandits vanished as quickly as they came,” declared the local paper.
On September 22, just a couple weeks after stealing more tan $21,000 from a bank in his hometown of Indianapolis, Dillinger was arrested by Dayton, Ohio police .
He was captured in the boarding house where his girlfriend, Mary Longnaker, lived, with “four pistols, $2,600 in cash, quantities of rifle and shotgun shells, detailed notes explaining the speediest ways to escape from various cities and sacks full of carpet tacks,” according to that day’s edition of the Dayton Daily News. Longnaker’s landlady had snitched him out.
As a repeat felon, there was no way Dillinger could avoid prison this time.
Escape And Adventure
In addition to the cash and guns John Dillinger was carrying at the time of his arrest, he had with him a cryptic document and a crudely drawn map. Dillinger refused to say what it was, but to the police it certainly looked like a prison escape plan.
And that plan, meant for eight of Dillinger’s friends, worked flawlessly. Using smuggled shotguns and rifles, the men broke out mere days after Dillinger’s arrest.
To return the favor, three of the escapees came back to the Lima, Ohio jail on October 12, this time disguised as Indiana State Police officers. They told the sheriff that they were there to return Dillinger to an Indiana penitentiary for violating his parole.
When the sheriff asked them for some identification documents, one of the convicts pulled a gun, shot him, and beat him until he was unconscious. They then fished out the key to Dillinger’s cell and broke him out. The gang then fled back to Indiana.
Hoover And The Bureau Of Investigation
By crossing a state border while fleeing a crime, the Dillinger Gang had committed an interstate offense. That, plus the death of the sheriff, drew the attention of FBI director J. Edgar Hoover.
After the gang robbed at least four more banks in different Midwestern states, the FBI coordinated with local law enforcement to ensnare the outlaws.
In January 1934, the Dillinger Gang robbed $20,000 from a bank in Indiana and fled to the southwest. Thanks to the FBI, police jurisdictions along the route were tipped off about the fugitives. Their intelligence paid off in Tucson, Arizona, where Dillinger was arrested 10 days after the robbery.
The chief of the Indiana State Police personally transported Dillinger back to Indiana to answer charges there, where he was locked up in the “escape-proof” Crown Point jail — or so they thought. That is, until Dillinger reportedly carved a fake gun out of wood and used it to escape.
He quickly reconnected with his gang, which now included the infamous cop-killing psychopath Baby Face Nelson. Now the subject of a nationwide manhunt, the crew holed up in Minneapolis and within a single week robbed banks as far apart as South Dakota and Iowa.
No Rest For The Wicked
By March 1934, Dillinger had moved into an apartment in St. Paul, Minnesota, reunited with an girlfriend, Evelyn Frechette.
Their nosy landlady took an interest in the couple, and on March 30, she had enough to go to the FBI field office and report her suspicions. The Bureau sent a pair of agents to check out her story, who were soon confronted by an enraged Dillinger bursting out the door and firing a tommy gun from the hip.
The agents returned fire, hitting Dillinger in the leg. The robber limped away, fleeing back to Mooresville with Frechette and holing up at the family home. After a week of recovery, Dillinger and his associates set out again toward Ohio.
It’s not entirely clear what they meant to do, but they were carrying multiple guns and a bullwhip. Later testimony indicated they were looking for one of Dillinger’s former lawyers to work off an old grudge. Unfortunately for them, on April 7, they accidentally rear-ended a couple on the road.
When their vehicle description was read over the radio, the local FBI swarmed the site, only to find the gang’s empty car on the side of the road.
Desperate Times Call For Desperate Measures
Two days later, on April 9, Frechette went to a meet a potential new landlord in Mooresville.
Smelling trouble, the robber held back in the car and sent her in first. As soon as she walked into the bar, FBI agents put her in handcuffs and hauled her off. She would never see Dillinger again.
He tried to rescue her, even using a hostage law enforcement officer to break into a police armory for bulletproof vests. However, the plan — crazy even by Dillinger’s standards — was eventually abandoned.
The wanted gangster next moved to Michigan’s Upper Peninsula and then Chicago, taking the alias of Jimmy Lawrence.
By now, the FBI had a dedicated Dillinger task force and called him “Public Enemy No. 1.” They even managed to find his abandoned car in the city. The FBI knew he was in town, but for several months the team worked without any leads.
Then, near the end of May, in another attempt to evade law enforcement, the gangster paid a plastic surgeon $5,000 to alter Dillinger’s appearance. He had some moles and scars removed, his famous chin cleft filled in, and his fingerprints burned off. “Hell, I don’t look any different than I did!” he supposedly said upon gazing in the mirror.
Still, the few alterations apparently were enough for him to pass by a couple of Dillinger Squad agents undetected at a Cubs game. Around this time, he also started dating the teenage runaway-turned-prostitute, Polly Hamilton.
The End Is Nigh
During their brief time together, Dillinger and Hamilton saw each other daily. On July 22, Dillinger suggested they see a show at the Biograph Theater, just around the corner from their hideout.
What he didn’t know was that Hamilton’s madam, Ana Cumpănaș, or Anna Sage, a Romanian immigrant facing deportation for running a brothel in Gary, Indiana had betrayed him.
Though Dillinger was still going by his alias, Sage recognized him from the wanted posters. Looking to cut a deal, she told the FBI everything she knew about Dillinger’s whereabouts. This allowed them to set up surveillance of the neighborhood he was staying in. (As it happens, she ended up being deported anyway.)
On the evening of July 22, while Dillinger and Hamilton were watching the show, the FBI task force surrounded the theater, splitting into two groups. The end seemed nigh for the famed bank robber.
The Death Of John Dillinger
In an unexpected turn of events, the theater’s manager called Chicago police after mistaking the agents for potential robbers. The police tried to arrest the agents before the situation was explained to them. However, it wasn’t enough to save Dillinger.
When the movie ended, Dillinger walked out with Hamilton — right past an FBI agent named Melvin Purvis, who lit a cigar to signal the others. According to Purvis’s testimony, Dillinger spotted the signal and turned to look across the street, where the other agents were drawn up.
This was just two months after famous Depression-era robbers Bonnie and Clyde had been machine-gunned to death. Dillinger seemed determined not to be taken as helplessly as they were.
Fishing in his pocket for his Colt pistol, he sprinted across the street to an alley that had already been blocked off.
Three agents followed him and fired six times, hitting him with four shots. Three shots were superficial. However, the one fired by Agent Charles Winstead entered through the back of Dillinger’s neck, clipped his brain stem, and popped out of his face under his right eye.
The 31-year-old bank robber was almost certainly dead before his body hit the pavement. It is rumored that John Dillinger’s last words were, “You got me.”
He was buried in a modest grave in Crown Hill Cemetery in Indiana, where his grave marker has had to be replaced four times — in a fitting tribute, thieves keep stealing pieces of the headstone.
John Dillinger’s Popular Personality
Even after John Dillinger’s death, many people continued to see him as a Robin Hood-type of character, because he robbed the banks that many people held responsible for the Great Depression.
In that sense, many Americans saw him as someone who robbed from the rich to give the the poor — a man of the people.
J. Edgar Hoover did not agree with that assessment. He famously quipped, “I cannot remember a single instance in which John Dillinger fancied himself a knight-errant, obtaining revenge upon a cruel world for past injustices. Rather, he was a cheap, boastful, selfish, tight-fisted pug-ugly, who thought only of himself.”
No matter which take you believe, at least his persona was big enough to be portrayed by Johnny Depp.
Regardless of who was right, Dillinger’s persona was big enough to inspire the 2009 movie Public Enemies, where he was portrayed by a fellow Midwestern John D., Johnny Depp.
Next, take a look at the story of Nucky Thompson, the real-life figure behind the acclaimed TV show Boardwalk Empire. Then, learn about the strange bank robbery behind Stockholm Syndrome.