Dillinger began his criminal career at the tender age of 20, when he boosted a car near Mooresville, Indiana and went on a joyride through Indianapolis. Confronted and nearly gunned down by police, he decided to enlist in the U.S. Navy to escape arrest. Dillinger later spent a few months shoveling coal aboard the battleship Utah, but the future gangster didn’t take well to military discipline. He was repeatedly censured for insubordination and going AWOL, and spent several days in solitary confinement before finally deserting for good in December 1923.
In September 1924, a 21-year-old Dillinger was sent to prison after being nabbed in a botched robbery on an elderly grocer. The young hood spent the next eight and a half years doing time with some of the Midwest’s most hardened convicts and getting a comprehensive education in the tricks of the criminal trade. Only days after winning parole in May 1933, a thoroughly unrehabilitated Dillinger hooked up with an Indianapolis gang and committed a series of grocery store and restaurant stickups. He graduated to bank robbery a few weeks later, kicking off the yearlong crime spree that would make him the nation’s most wanted gangster.
Dillinger committed a string of high profile heists during the summer of 1933, but he was desperate to reunite with some of his old prison buddies to form an ace bank robbing gang. That September, he began plotting to break his would-be accomplices out of the Indiana State Prison at Michigan City. Dillinger conspired to have three .38 pistols hidden in a crate of thread bound for the jail’s shirt making factory, allowing 10 convicts—including experienced stickup men “Handsome” Harry Pierpont, Charles Makley and John Hamilton—to get the drop on their guards and escape. The timing couldn’t have been better. Dillinger had been arrested at a girlfriend’s house only a few days before, and was languishing in jail in Lima, Ohio. On October 12, the newly liberated Pierpont and two other men waltzed in the front door and busted him out, gunning down the county sheriff in the process.
While most criminals stayed as far away from lawmen as possible, Dillinger was willing to march right into their headquarters with gun in hand. Shortly after being sprung from jail in October 1933, Dillinger and his band carried out a pair of audacious heists on the police stations at Auburn and Peru, Indiana. As bewildered deputies looked on, the gangsters emptied their gun cabinets of Thompson submachine guns, shotguns, rifles, tear gas guns, bullet proof vests and more than a dozen pistols. The crooks immediately put the arsenal to use committing a wave of bank heists that left two police officers dead.
Dillinger’s famous robberies and getaways saw his face splashed across newspapers and newsreels as much as some Hollywood stars. An Indianapolis lottery on when he would be captured proved so popular it had to be shut down, and his father was offered a small fortune to do public speaking engagements. When Dillinger and his gang were arrested in Tucson, Arizona, scores of people filed through the city jailhouse just for the opportunity to lay eyes on the dashing criminal. Businesses even used him as an unsanctioned celebrity endorsement. Upon learning that the car-loving outlaw drove their automobile, one Hudson dealership hung a banner reading, “Dillinger Chooses the 1934 Hudson For His Personal Use.” When the robber later switched to a Ford, the company printed brochures saying, “Will they catch John Dillinger? Not until they get him out of a Ford V8!”
Dillinger was arrested in Tucson, Arizona in January 1934, after locals recognized a few of his heavily wanted accomplices. Following a flurry of media coverage, he was extradited to Indiana and confined to the jail in Crown Point to await trial. Authorities boasted that the jail was escape proof, but Dillinger would only remain a resident for a little over a month. On March 3, 1934, he forced his way out of the main cellblock by brandishing a phony gun. Dillinger claimed he had fashioned it from a block of wood, a razor handle and a coat of black shoe polish, but reports would later suggest it was smuggled into the prison by one of his attorneys. In any case, Dillinger used the wooden pistol to round up several guards and get his hands on a Thompson submachine gun. Once armed with real firepower, he made his way to the prison garage, stole the sheriff’s personal police car and motored to Chicago. Amazingly, Dillinger was back in action only three days later, teaming with gangster Baby Face Nelson and others to knock over a bank in Sioux Falls, South Dakota.
By late-May1934, Dillinger’s reputation—and his easily recognizable mug—was beginning to catch up to him. He’d been shot in the leg during a shootout with agents from the FBI (then known as the Division of Investigation) in late March, and had only narrowly escaped an ambush by G-Men at a resort in Wisconsin a month later. Desperate to change his appearance, he paid $5,000 to enlist the services of Wilhelm Loeser and Harold Bernard Cassidy, a pair of underworld plastic surgeons. After anaesthetizing Dillinger with ether, the doctors gave the gangster a rudimentary facelift, removed several moles and scars, filled in his famous cleft chin and used chemicals to burn off his fingerprints. The procedure proved excruciating, and Dillinger was decidedly unsatisfied with the results. Upon looking in the mirror, he supposedly exclaimed, “Hell, I don’t look any different than I did!”
Dillinger spent most of July 1934 holed up in a Chicago apartment with new girlfriend Polly Hamilton and brothel owner named Anna Sage. He successfully evaded police for most of that month—even attending Chicago Cubs baseball games—but his days were numbered. After the price on his head soared to $25,000, the Romanian-born Sage contacted the FBI and offered to give him up for part of the reward money as well as aid in avoiding deportation. On July 22, 1934, federal agents were watching as Sage, Hamilton and Dillinger went to see the Clark Gable crime film “Manhattan Melodrama” at Chicago’s Biograph Theater. When the trio stepped out onto the sidewalk shortly after 10:30 p.m., agents closed in with guns drawn. Dillinger struggled to pull a.380 automatic from his pocket, but was quickly cut down in a hail of bullets. He died on the scene.
Dillinger and his gang robbed at least a dozen banks and netted a total loot of around $500,000 (roughly $7 million in modern day currency), but his take paled in comparison to the amount of money the FBI spent trying to catch him. According to the Associated Press, the nascent government agency racked up a tab of some $2 million on the manhunt, which included the bill for several agents dedicated solely to Dillinger. Historians have since credited the hunt for John Dillinger—and his eventual death at FBI hands—with helping legitimize the Bureau and establish it as the nation’s most famous crime unit.
Dillinger’s astonishing celebrity became more apparent than ever after his death. Souvenir-hunters dabbed handkerchiefs in his blood at the scene of the shooting, and thousands of people lined up to view his bullet-riddled body when it was put on display at the morgue. A mob of spectators later gathered at the funeral home, and despite efforts to keep its date a secret, more than 5,000 people appeared at the cemetery for his burial. Dillinger’s casket was encased in cement to deter grave robbers, but his headstone later had to be replaced several times after people claimed pieces of it as keepsakes.