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John Dillinger was born on June 22, 1903 in Indianapolis, Indiana. The son of a well-off, hard-working grocer, he resented his father remarrying after his mother died. His teenage years were spent in pool halls, where he hung out with hardened criminals. Lacking any form of career prospects, he joined the navy when he was twenty but soon went AWOL. The navy clearly did not want him back since he was able to rejoin his family and marry his sixteen year old girlfriend. Unwilling to work, he returned to loafing around pool halls. While robbing a local grocer with one of his pool hall friends on September 6, 1924, he panicked and shot the man. The judge wanted to use him as an example to other first time offenders, so Dillinger received a sentence of ten to twenty years. While in prison he became friends with Harry “Pete” Pierpoint and Homer Van Meter, and he joined them when they were transferred to the state prison at Michigan City, which was populated by real hard cases.

In May 1933, his family, with the support of the original judge and the man he had mugged, won Dillinger parole. Although he had promised his father that he would go straight, Pierpoint and Meter persuaded him to smuggle guns into the prison as part of their plan for a mass breakout, promising that he would join their gang afterwards. Newspaper headlines meant that Dillinger was all too aware of the potential rewards of such a career, so he agreed and received an education in the science of robbing banks.

After holding up his first bank on June 10, Dillinger was preparing to hit another bank but the police caught the rest of his gang on July 15 while he and Harry Copeland were moving his new car, so they missed being arrested. The two men robbed the bank as planned and made off with $3,500. They then took $10,000 from the First National Bank in Montpelier, Indiana on August 4. In mid-September, he arranged for guns to reach his friends, including Russell Clark, John “Red” Hamilton and Charles Makley, which ensured the success of their breakout on September 26, although three of the ten men ended up dead or recaptured.

Dillinger’s crime spree attracted the attention of the police, and the captain of the Indiana State Police, Matt Leach, cooperated with insurance companies to hunt him down. A Pinkerton agent learned the name of a woman that Dillinger was seeing in Dayton, Ohio, which was given to the police, and they arrested him on September 22. Witnesses were then brought in from Indiana and Ohio to identify him for several bank robberies. On October 12, his friends returned the favor and broke Dillinger out of the small town jail in Ohio where he was being held while he was standing trial for a previous robbery in the area, killing Sheriff Jess Sarber in the process. Dillinger joined the gang, which then raided two police stations in small Indiana towns to build up its arsenal. On October 23, they took $75,000 from an Indiana bank in an operation so smooth that no one in the sheriff’s office across the street even noticed.

The rampage caused the governor of Indiana to order out the National Guard, and although calls went out to the FBI, director J. Edgar Hoover knew that he lacked the resources for such a huge manhunt, so the gang was ignored. Dillinger and Pierpoint shared a large apartment in Chicago with their girlfriends, spending their days shopping and their nights in clubs. Although they never made new friends, they did keep in touch with other alumni of the Indiana State Prison and an insurance investigator managed to get an informant close to the gang. However, the state police was only interested in Dillinger, while the Chicago police wanted the whole gang. After a series of debates, the Chicago police agreed to capture Dillinger on November 14 when he was on his own, instead of taking the risk of missing both him and the gang. A trap was set up with a car ready to block every possible escape route but he noticed the odd arrangement of the cars and reversed his car into oncoming traffic, while a flooded engine prevented a police car from blocking that route. Dillinger originally thought that it had been a syndicate hit and was relieved to read in the next day’s newspapers that it had been the police.  

Instead of lying low, the gang robbed the American Bank and Trust Company in Racine, Wisconsin on November 20 but the head teller managed to press the alarm button even though he had been shot. Two officers sent to check it out were immediately captured but the third escaped to get help. The outlaws remained calm but it was clear that more police would arrive in moments. Unfortunately, during their planning they had failed to notice that the bank did not have a back door, but the getaway car was parked in the back. The problem was solved by taking three hostages when they drove off. Afterwards, all of the witnesses agreed that Dillinger had behaved like a gentleman, probably because he was well aware of his public image as a form of vengeance against the powerful, rich men who had caused the Depression.

The outlaws’ celebration ended on December 14 when a Chicago police officer sent to investigate a garage believed to be repairing their cars was killed by a panicky member of the gang. Realizing that the Chicago police department would not take this lying down, Dillinger and the rest of his partners understandably felt it was time for a vacation and spent the holidays in Florida.

On the way back from Florida, Dillinger decided to rob a bank in Indiana with only John “Red” Hamilton and an unknown getaway driver on January 15. Calm as ever, he told the customers he only wanted the bank’s money but when they left with hostages, they found seven policemen waiting instead of the usual chaotic crowd. A detective shot Dillinger, or rather his bulletproof vest but the officer did not have a vest himself and died when an irritated Dillinger fired back. The outlaws escaped but the death of a father of three girls ended his Robin Hood image and he spent the rest of his life denying the killing.

Dillinger met up with the rest of the gang in Tuscon, Arizona but the gang became a little too relaxed and attracted attention, which was unwise since their photos were already circulating across the nation. The local police managed to calmly and efficiently arrest each member of the gang one by one during the evening of January 25. Once the outlaws were in jail the real fight began between Wisconsin, Indiana and Ohio over who would prosecute first. Indiana won because Dillinger had killed a detective there, and he faced the electric chair. Pierpoint and the rest of the gang were sent to Ohio to stand trial for killing Sheriff Sarber.

Fed up with Dillinger’s habit of escaping, the Chicago police assigned thirteen police cars and a dozen motorcycle cops to escort him from the Chicago airport to Crown Point, whose sheriff, Lillian Holley, had inherited the position after her husband, the previous sheriff, had been killed. During a press conference Dillinger did not deny that he robbed banks and the reporters ate up his easygoing manner. In fact, the press would portray him so favorably that he became a national celebrity with fans even among people who traditionally condemned criminals. Gangland lawyer Louis Piquett was persuaded to represent him and he ensured that Dillinger remained in Crown Point instead of being transferred to the more solid Michigan City Prison by insinuating that Sheriff Holley was worried that she could not handle the responsibility and by reminding the judge that all of the media attention would disappear if Dillinger was moved.

Dillinger broke out of the Crown Point jail on March 3 by taking a janitor hostage when he was cleaning the cells. He used the janitor to lure in one guard and then the guard to lure in first the warden and then four more guards, who were locked up in the cell. Apparently, no one thought that it was odd that guard after guard was disappearing. Once the guards were all locked up, he took the two submachine guns from the warden’s office, keeping one for himself and giving the other to Herbert Youngblood, who was the only prisoner to agree to his plan. Just before leaving, Dillinger showed the guards that the gun was made out of wood. He captured almost fifteen people and then stole the sheriff’s V-8 Ford because it was the fastest car in the jail. When they reached Chicago, the two men parted company and Youngblood died in a shootout with police in Michigan two weeks later. After thanking Piquett for arranging the escape, Dillinger hooked up with Baby Face Nelson’s gang the next evening.

Following Dillinger’s escape, the recriminations began. The janitor and the guard who were used to lure the other guards into the cell were quickly acquitted, while the guards could not agree on whether Dillinger had used a wooden gun or a real gun. It was believed that Piquett had smuggled in the wooden gun but no one knows who did it. After the break out at Crown Point, the governor of Ohio called out the National Guard and machine guns were set up around the courthouse to ensure that Dillinger did not rescue his former partners. Pierpoint and Makley received death sentences and Clark got life.

Nelson was irritated that the press immediately labeled the gang the John Dillinger Gang and Dillinger was uncomfortable with Nelson’s itchy trigger finger but beggars can’t be choosers and Nelson had a gang, while Dillinger had legal bills. The national headlines that followed their first bank robbery at Sioux Falls, Dakota on March 6 forced Hoover to make the hunt for Dillinger a priority. The head of the Chicago FBI office, Melvin Purvis, had a lucky break when an acquaintance of Dillinger set him up but incompetence meant that Purvis only nabbed Dillinger’s girlfriend Billie Frechette. Meanhwile, tension in the gang had reached dangerous levels, so they decided to go to a resort in northern Wisconsin called Little Bohemia for a break. The owner of the lodge realized who they were and contacted the FBI but the inexperienced agents killed an innocent man on April 22 and allowed the outlaws to escape in the confusion.

While it was a huge embarrassment for the FBI, Dillinger had to live on the run for three weeks before Nelson and Piquett arranged for him to stay with a fence named Jimmy Probasco. More important, Dillinger received plastic surgery, which enabled him to enjoy baseball games and nightclubs. Although Dillinger and Nelson managed to suppress the friction long enough to rob a bank together on June 30, he and Van Meter felt that Nelson was too volatile, so they decided to cut relations with him a few days later.

However, Dillinger worried that Probasco’s heavy drinking might attract attention, so he left on July 4 and moved in with his new girlfriend Polly Hamilton and two other people, Anna Sage and her son. Sage had made her living running brothels, relying on corrupt Chicago detective Martin Zarkovich for protection. However, her brothel was too brazen and violent for Zarkovitch to cover up, so it was closed down in 1932. Worse, her file was sent to immigration authorities for deportation. By 1934, she was living in Chicago and was believed to be using her apartment as a part-time brothel. Although Hamilton’s official profession was waitress, the FBI believed that she had met Dillinger while moonlighting as a prostitute. With his girlfriend in prison, Dillinger was lonely and he fell hard for Hamilton, romancing her with baseball games and movies in the day, and nightclubs at night.

While no one spotted Dillinger on the street, he had let too many people get close to him and the $15,000 reward would prove irresistible. Dillinger’s plastic surgeon mailed an anonymous letter to the FBI on July 23 explaining the work that had been carried out on him. On July 17, Dillinger learned that Probasco and Piquett were apparently discussing turning him in. However, Sage had received a letter on July 12 from the U.S. immigration service saying that her appeal had been denied and she would be deported, so she used Zarkovitch as her intermediary to contact the FBI. When Purvis met with Sage on Sunday July 21 he promised to help with the deportation but could not make any guarantees. While Purvis and the other agents may have had their doubts about her story all they cared about was whether she could deliver Dillinger. Sage said that they were planning to go to a movie on Monday, so she would call Purvis when she knew which one, and she would wear an orange dress to identify herself.

Hoover informed senior field agent Sam Cowley that he wanted Dillinger taken alive if possible. Given the FBI’s track record with Dillinger, Cowley was less optimistic and told his agents to use their own judgment about whether to shoot to kill. Unfortunately, Sage was not able to say whether it would be the Biograph or the Marbro theater, so Purvis went to the Biograph, Zarkovitch staked out the Marbro and Cowley stayed in the office to coordinate. After a very stressful waiting period, Dillinger showed up at the Biograph with the two women. They went inside the theater too quickly to be taken but it was clearly him and he had not brought Van Meter or Nelson. Since he was inside the theater, they had enough time to arrange for the agents and police to block every possible exit. When Dillinger came out of the theater Purvis gave the assigned signal, which was lighting his cigar but only a handful of agents saw it. The delay meant that Dillinger figured out it was a trap and he was reaching for his gun when three FBI agents started firing without taking the time to identify themselves. Four bullets hit him and one was fatal, although the FBI refused for decades to reveal who had fired the shot that killed Dillinger. The agents defended their failure to warn him by saying that when a man like Dillinger reaches into a pocket you start shooting. Although the body was quickly taken away dozens of people put their hankerchiefs into the pool of blood that was left.

It became a headline story around the world the next day. Purvis gave numerous interviews where he happily took the credit and neglected the role played by the East Chicago police. Reporters somehow learned that Dillinger had been betrayed by a woman in red and when Sage was pulled in by the police, Cowley refused to bail her out or even admit that he knew her. When the police announced that they intended to hold her overnight for more questioning, Cowley put her into protective custody. Dillinger’s plastic surgeon was arrested soon after and he directed them to Probasco. Unfortunately, Probasco was left alone long enough to kill himself by jumping out the window. Piquett was picked up as well and he received two years in prison.

Captain Leach had an informant who stated that Zarkovich had protected Dillinger and wanted the FBI to investigate the matter. However, Cowley was reluctant because if it was true then the Bureau would look bad for cooperating with a corrupt cop. In the end, they ignored Hamilton and Zarkovich’s testimony and relied on Sage’s statement. Cowley then told Sage to hide herself in Los Angeles and later handed over her share of the reward, $5,000, personally. However, she was still deported to Romania.

Dillinger was buried in his home town and five thousand people watched the funeral.

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Related Movies:

Dillinger (1945)
Directed by Max Nosseck, starring Lawrence Tierney and Anne Jeffreys
It shows the rise of John Dillinger from petty criminal to bank robber and finally Public Enemy Number One.

Dillinger (1973)
Directed by John Milius, starring Warren Oates and Ben Johnson
Following the death of several FBI agents during the Kansas City Massacre, FBI agent Melvin Purvis vows to capture or kill a number of famous outlaws including Machine Gun Kelly, Pretty Boy Floyd, Baby Face Nelson, and John Dillinger. (please click here to read the review)

Further Reading:

Public Enemies: America’s Greatest Crime Wave and the Birth of the FBI, 1933-34. Bryan Burrough, New York: The Penguin Press, 2004.

The author grew up listening to stories about Bonnie and Clyde, and decided to write the book because there was no single history of that period, partially because the FBI files had only been released in the late 1980s. His access to previously sealed FBI files means that the story is as much about the evolution of the FBI as it is about the gangsters themselves. It is a superb, one-stop look at that brief period where outlaws seemed to roam free. Ignoring the easy approach of dividing the book into several sections that focus on individual gangs, the story is told in chronological order, which might appear confusing to some readers but serves to show how interrelated the events were. Most of the gangs knew each other and their paths crossed more frequently than I would have thought, which may help to explain why the FBI was so confused in the beginning. Burrough’s attention to detail is impressive, he shows what happened to the main FBI agents, the surviving outlaws who ended up in prison, and their various girlfriends and accomplices. What is odd is that once the War on Crime was over, no one really talked about it. The agents rarely told their families, while the families of the outlaws often preferred to move forward and leave their tainted past behind them.

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