On 6 September 1924, Dillinger was with a friend, Edgar Singleton, who allegedly introduced the young would-be gangster into a life of felony. Being more experienced in criminal society, Singleton had considerable influence over the young Dillinger and coerced the him into robbing a local grocer, Frank Morgan. As the shopkeeper returned home with the week’s takings, the two men assaulted him.
Dillinger hit Morgan with a cloth-wrapped iron bolt and the victim fell to the ground. Both men were arrested and, despite Dillinger being the younger of the two and having no criminal record, he found himself facing the stiffer penalty - between 10 and 15 years in prison. The canny Singleton, despite actually having a criminal record, engaged the services of a lawyer and received a lesser 2 to 14 years behind bars.
While in prison the young Dillinger wrote a remorseful letter to 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.”
Inside the Indiana State Reformatory he kept his head down and showed that he could be an industrious prisoner in the shirt factory, where he worked as a seamster. He was so conscientious that he not only completed his own quota twice over but also did other prisoners’ work too.
It is more than likely that Dillinger knew exactly what he was doing; ingratiating himself with powerful fellow cons such as Harry Pierpont and Homer Van Meter who quickly sought his friendship.
Despite being estranged from his wife, Beryl and his family visited him frequently. He also wrote warm tender letters to his wife, signing himself as ‘Hubby’ but little knowing that Beryl was contemplating a divorce. Even though she received a letter asking to send pictures of herself and telling her how much he’d care for her when he got out, Beryl filed for divorce on 20 June 1929. Dillinger was devastated. It was not to be the only blow, for one month later he discovered that his case for parole had been rejected.
If Dillinger wasn’t the hardened criminal, intent on a life of crime when he first went into prison, there is no doubting that his experiences inside the Indiana State Prison firmly set him on course for a life of crime. He was now a bitter, angry creature, and soon schooled up on the skills of robbing banks with guidance from the likes of Pierpont, Van Meter, Charles Makley, John Hamilton, Walter Dietrich and Russell Clark. When they finally broke out of prison, these men would all become members of the Dillinger gang.
On 22 May 1933, Dillinger was paroled. After having spent most of his youth incarcerated, the now hardened ex con decided he was going to become a professional bank robber. Now on the outside, he was in a position to help smuggle in guns to his friends via Harry Pierpont’s girlfriend, Mary Kinder. On 22 September, ten prisoners, Dillinger’s new disciples, escaped from the Indiana State Prison.
Just before their escape, Dillinger himself had been arrested and imprisoned at the Allen County Jail in Lima. In a scene reminiscent of a Western, the escaped convicts, including best friend Pierpont, sprang Dillinger from jail – however, in the process they killed Sheriff Jesses Sarber.
It is alleged that Dillinger was angered by the death, as he felt it unnecessary. But such regrets didn’t stop him from planning raids on several banks using rigorous methods that involved meticulous planning and trial-runs before undertaking the actual attack. Part of his master plan entailed memorising the interior layout of a bank, also noting its distance from the local police station.
As Dillinger and his gang’s bank sprees went from state to state, their reputation with the public - enhanced by the fact the Depression had meant banks had foreclosed on millions of people – became almost saintlike. Unwittingly perhaps, Dillinger began to cultivate a ‘Robin Hood’ hero-like status, acting as avenger for the way millions of ordinary American citizens had been treated.
In April 1934, Warner Brothers studios released a newsreel showing the Division of Investigation manhunt of John Dillinger, by now one of the nation's most notorious criminals. Movie audiences cheered when Dillinger's picture appeared on the screen. Conversely they hissed at pictures of D.O.I. special agents. When D.O.I. Director J. Edgar Hoover heard the news that movie audiences, particularly in Dillinger’s hometown of Mooresville, were applauding the mobster he was outraged. Hoover put the town of Mooresville under surveillance, and threatened to prosecute the Dillinger family unless they cooperated with the D.O.I.
Aside from Dillinger’s busy schedule robbing banks he wasn’t averse to developing his love life and began a relationship with Evelyn Billie Frechette, a girl of mixed French and Native American ancestry. His fellow gang members also had girlfriends, but apart from sex there were few other indulgencies as Pierpont, a stickler for discipline believed that drink and drugs would make them less alert to the danger of being caught.
Although it’s fair to say that few citizens were killed because of Dillinger’s exploits, that wasn’t to say that innocent people, either those working in banks or passersby weren’t traumatised by the experience of being caught up in a raid.
On 15 January 1934, Officer Patrick O’Malley was shot and killed by Dillinger during a bank raid in East Chicago. Although there is some contention over who was actually responsible for the family man’s death, Dillinger is reported as saying "I've always felt bad about O'Malley getting killed, but only because of his wife and kids. ...He stood right in the way and kept throwing slugs at me. What else could I do?"
Ten days later on 25 January 1934, Dillinger, along with Pierpont, Makley and Clark were arrested in Tucson. They were split up, Dillinger himself being extradited by plane to Indiana for the murder of Officer O’Malley while the others went to Lima prison, Ohio. Dillinger didn’t go quietly, needing to be shackled and dragged to the aircraft. During this time on trial, the famous photograph was taken of Dillinger putting his arm on prosecutor Robert Estill's shoulder.
After residing in ‘escape-proof’ Crown Point prison in Indiana, Dillinger eventually absconded in an episode which has become part of gangland folklore, when he allegedly threatened guards with a wooden gun blackened by shoe polish. The mobster himself was quoted as referring to it as his ‘pea shooter’.
Later, evidence emerged that his lawyer had arranged for Dillinger's escape with cash bribes and the wooden gun was simply a cover story.
But it was still an audacious jailbreak with Dillinger stealing the sheriff's car and racing off to Chicago. J. Edgar Hoover was ecstatic, because driving a stolen vehicle across state lines was a federal crime, making Dillinger eligible for a pursuit by the FBI.
Continuing their spree, hitting banks in the Sioux Falls, South Dakota, and Mason City, Dillinger was eventually wounded in the shoulder during a raid in Iowa. He then lay low with girlfriend Billie Frechette at the Lincoln Court Apartments in St. Paul. However, the caretaker of the building was suspicious and, after reporting to the authorities, two FBI agents paid a visit to Dillinger’s apartment.
Frechette opened the door and the agents asked to talk to ‘Carl Hellman’ - an alias Dillinger used. At first Frechette told the agents he wasn't there and when they then asked to speak with her she told them to wait while she dressed. After a few minutes, Dillinger cleared the way with a machine gun and he and Frechette escaped after one of the agents receiving a leg wound. After a brief recuperation the couple decided to head to Mooresville, Dillinger’s home town, which they believed would be the last place the FBI would look for them.
However, events were to take a rather bizarre turn when Dillinger’s girlfriend was finally caught and arrested in Chicago. The then increasingly paranoid Dillinger decided to undergo plastic surgery, along with Van Meter, on 27 May 1934.
After his jailbreak and continuation to rob banks across several states Dillinger, who turned 31 on 22 June 1934, became America’s first 'Public Enemy Number One' - with a $10,000 reward on his head.
It was around this time that a new member joined the Dillinger posse, the psychopathic George Nelson, otherwise known as ‘Baby Face Nelson’ due to his youthful features.
It was while the gang were on the run and staying at a lodge called Little Bohemia in Wisconsin that a shootout occurred between Dillinger’s gang and the FBI after agents had been secretly contacted by the lodge owners. After FBI agents crept up on the lodge, Dillinger and his gang were alerted by barking dogs and soon gunfire was exchanged. The brief battle resulted in Baby Face killing thirty-year-old agent W. Carter Baum after the agent had approached the mobsters’ car.
The incident also saw terrible mistakes committed by the FBI themselves when they mistakenly gunned down three innocent workers during the shootout. However, despite the short, intense exchange of fire, Dillinger and his gang managed to escape.
On 4 July 1934, Dillinger moved into the apartment of Anna Sage, a Romanian ex-prostitute who was facing deportation charges for operating several brothels. Not one to be without a woman for long, Dillinger now had a new girlfriend, Polly Hamilton, former waitress and employee of Sage.
It’s not known whether Dillinger was aware that Sage was facing deportation charges but he obviously wasn’t aware of the fact that she was prepared to double cross the mobster in order to save her own skin.
Sage did a deal with Melvin Purvis, a young, well-respected FBI agent who was to later become famous for capturing more public enemies than any other FBI agent in history. The brothel owner believed that by turning Dillinger in she wouldn’t be deported – she would be sorely mistaken.
On 22 July 1934, Dillinger invited Sage and girlfriend Hamilton to see the Clark Gable movie ‘Manhattan Melodrama’ at the Biograph cinema in Chicago. Sage had forewarned Purvis and when the trio set off to see the film, FBI agents, including Purvis, waited outside. Sage, who had been asked to wear an orange skirt and white blouse to identify her, knew all along that agents were waiting outside.
As the trio exited the cinema Purvis shouted “Stick ‘em up, Johnny”.
Dillinger bolted, running down the street and struggling to take his gun out. He was shot six times in the back.