Public Enemy Number One: The FBI’s Ambush of John Dillinger

He carried out a string of often flamboyant bank robberies during the Great Depression, he became a dapper Robin-Hood-like folk hero to many, he bragged that no jail could hold him (and broke out of jail twice–once with a wooden pistol), and he defied the newly-formed FBI who proclaimed him “Public Enemy Number One”. He was the most famous of all the Depression-era outlaws, to the point where the 1930’s crime period is often called “The Dillinger Era”. But in the end, the long arm of the law finally caught up with John Dillinger . . .


The Biograph Theater, in Chicago, where John Dillinger was killed.

John Herbert Dillinger was born in 1903, in Indianapolis. His father was a strict disciplinarian who owned a grocery shop and a few rental houses. His mother died just before his fourth birthday, and he was cared for mostly by his older sister Audrey until his father remarried in 1912. In 1919, Dillinger dropped out of school and took a job in a machine shop. The next year, Dillinger’s father retired, sold his properties, and moved the family out of the city and on to a farm in Mooresville, Indiana.

In July 1923, Dillinger had his first run-in with the law. After stealing a car to impress a girl with a joyride, Dillinger dumped the car but was found by a policeman who placed him under arrest. Dillinger managed to break free and run away, and knowing that he’d be arrested again, he signed up with the US Navy the next day. After basic training, he was placed aboard the battleship Utah, but after just a few months, Dillinger decided that military life was not for him, so he jumped ship in California, went AWOL, and returned to Indiana.

There, the 21-year old Dillinger met and married 16-year old Beryl Hovious, and they moved into his father’s farmhouse. After Dillinger was arrested for stealing a neighbor’s chickens, the couple moved into the home of Hovious’s parents in nearby Martinsville.

In 1924, Dillinger was befriended by Edgar Singleton, a local tough with a police record who was a distant relative of Dillinger’s stepmother. That September, the two of them robbed a local store owner named Frank Morgan. Dillinger was to carry out the robbery while Singleton waited nearby in the getaway car. Morgan, however, was able to grab Dillinger’s pistol, and in the struggle the gun went off. Dillinger ran, but Singleton, hearing the gunshot, had already taken off in the getaway car.  Dillinger was caught by police shortly later. Unable to afford a lawyer, Dillinger appeared in court alone and was given a 10-20 year sentence for the robbery; Singleton, meanwhile, had a lawyer and got off with serving just two years, despite the fact that he was older than Dillinger and had a prior record. Dillinger always resented the unfairness of his sentence, and years later would write, in a letter to his father, “If I had gotten off more leniently when I made my first mistake this would never have happened.”

Dillinger was sent to the Indiana State Reformatory in Pendleton, where he joined the prison baseball team, worked in the textile shop, and befriended a number of experienced bank robbers, including Harry Pierponte, Homer Van Meter, Russell Clark, and Charles Makley. When Pierpont and Van Meter were transferred to Indiana State Prison, Dillinger requested a transfer there too, telling prison officials it was because the State Prison had a better baseball team. While in the State Prison, he met fellow prisoner Walter Dietrich, who had been partners with the legendary bank robber Herman Lamm. Lamm, a former Prussian soldier, was the first bank robber to meticulously plan his heists with military precision, casing out banks for weeks beforehand and carefully making detailed plans for every possible contingency.

In May 1933, Dillinger was released on a humanitarian parole when his stepmother became seriously ill (she died shortly before Dillinger arrived home). Dillinger promptly made contact with several associates of his prison friends and, on June 10, 1933, robbed his first bank, in New Carlisle, Ohio. The gang robbed several more banks, then made plans to bust their friends out of the Indiana State Prison. Dillinger smuggled a number of guns inside to the prison laundry room, where they were used by Pierpont, Clark, Makley, Dietrich and six others to escape. They fled to a safehouse in Hamilton, Ohio.

Dillinger, meanwhile had been arrested for the Ohio bank robberies and was now in jail in Lima, Ohio. Pierpont and his gang decided to bust Dillinger out–they arrived at the County Jail pretending to be state officials who were taking Dillinger back to Indiana State Prison. When the Sheriff, Jess Sarber, asked to see their ID’s, Pierpont shot him. Dillinger and the gang fled to Chicago. Shortly afterwards, they raided a police arsenal in a small town in Indiana, getting away with shotguns, pistols and Thompson submachine guns.

The Dillinger Gang then carried out a string of bank robberies in Illinois, Indiana, and Wisconsin. Some of these robberies have entered the realm of legend, and it is no longer clear what is true and what is not. (It’s not even clear how many banks they robbed, since the police and press often blamed the Dillinger Gang for any unsolved robbery.) In one instance, the gang reportedly posed as bank-alarm salesmen to get access to the vault. In another story, they presented themselves as a film crew scouting a location to shoot a movie about a bank robbery–then proceeded to rob the bank for real. In one widely-reported instance, Dillinger asked a farmer standing in line at the bank window if the money he was holding was his or the bank’s–when the farmer told him it was his money, Dillinger told him to keep it, saying he only wanted to take money from the banks. For many people, the Dillinger Gang became a mythical sort of Robin Hood, robbing the rich banks who had made everyone’s lives miserable in the Depression by taking away people’s life savings and by foreclosing on farms and houses. In some versions of the legend, the Dillinger gang destroyed the bank’s mortgage records so they could not foreclose on anyone.

In December 1933, one of the gang members who had gone to pick up a car at a garage got into a shootout and killed a local police officer. In response, the Chicago Police established a “Dillinger Squad” to find him. Dillinger and his gang fled to Florida, then to Arizona. On the way, they robbed a bank in Gary, Indiana, and in the ensuing shootout Dillinger was shot several times by a local cop named O’Malley, but was unharmed because he was wearing a bulletproof vest. Dillinger returned fire, killing him.

When they arrived in Tucson, the entire gang was surrounded by police and arrested–each of them was extradited to various states, with Dillinger ending up in Crown Point Prison, Indiana, awaiting trial for the murdered police officer. The press swarmed him and took a number of photos of the dapper Dillinger posing and joking with his captors. Dillinger expressed regrets that the police officer had been killed, reportedly telling his lawyer, “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?”

The trial never happened. According to legend, while in jail Dillinger broke a piece of wood from a washboard, used a razor to whittle it into the shape of a pistol, blackened it with shoe polish–then used it to escape. In another version, an investigator who worked for Dillinger’s lawyer claimed that he had helped smuggle a real gun into the prison. In still another version, Dillinger’s “escape” was arranged with the payment of huge cash bribes through his lawyer to the local police. In any case, Dillinger stole the Sheriff’s car and fled to Chicago. It was a big mistake–by crossing a state line with a stolen vehicle, Dillinger had committed a Federal crime, and was now in the sights of the FBI.

Established in 1908 as the “Bureau of Investigation”, the Federal Bureau of Investigation (following several name changes) was now run by J Edgar Hoover, a man of overwhelming ambition. Determined to make the FBI the premiere law enforcement agency in the country, Hoover successfully lobbied for a number of changes in the law that would give him steadily greater jurisdiction, particularly over high-profile crimes. Hoover gave the task of tracking down America’s most-wanted bank-robber to Chicago FBI chief Melvin Purvis. His agents were known as “G-men”.

Once in Chicago, Dillinger formed another gang, which now included his old prison pal Homer Van Meter, a local career criminal named Lester Gillis–more widely known as “Baby Face Nelson”, and Dillinger’s girlfriend Evelyn “Billie” Frechette. The new gang moved to St Paul, Minnesota, and over the next four weeks robbed six banks in four different states. The FBI tracked them to St Paul and went to their hotel room. In the ensuing shootout, Dillinger, Van Meter, Nelson and Frechette escaped, with Dillinger being slightly wounded. They fled to Dillinger’s family farm at Mooresville. Purvis’s men followed them, and when Frechette drove back to Chicago a few days later, the FBI arrested her. Dillinger and the rest of the gang had gone to the Little Bohemia Resort in Wisconsin, stopping along the way to rob a police armory in Indiana.

On the night of April 23, 1934, the FBI surrounded the Little Bohemia Lodge. When three men entered a car in the parking lot, the FBI opened fire, thinking it was the Dillinger gang trying to escape. In reality, they were innocent resort guests. One was killed and the two others wounded, and the FBI’s gunfire alerted Dillinger and Baby Face Nelson, who came out shooting. One FBI agent was killed, and the entire gang escaped. The FBI put up a $15,000 reward for information leading to his capture.

Dillinger ended up in the house of a Chicago bar owner with gangster connections, where he paid a doctor to perform plastic surgery on him to alter his appearance, and spent the next month recovering from the surgery. On June 30, 1934, Dillinger carried out what would be his last bank robbery. Accompanied by Baby Face Nelson and Van Meter, Dillinger entered the Merchant’s National Bank in South Bend, Indiana. When Nelson dramatically sprayed the ceiling with machine-gun fire, it alerted the local cops, and a wild shootout ensued in which several civilians were wounded.

In July 1934, the FBI office in Chicago was contacted by Anna Sage, a local brothel owner from Romania who was in the middle of deportation proceedings. Dillinger and his new girlfriend, Polly Hamilton (who was a friend of Sage’s), were staying in one of her roominghouses, and Sage offered to tip the FBI off to his whereabouts if she were given the reward money and if the deportation would be stopped. Purvis agreed, and on Sunday July 22, Sage contacted the FBI to tell them that she, Hamilton and Dillinger would be going to the movies that evening, but she didn’t know if they would be at the Biograph Theater or the Marbro. She also told them that she would be wearing an orange dress so they could easily recognize her. The FBI sent men to stake out both theaters, and waited.

At 10:30pm, Dillinger came out of the Biograph Theater with Polly Hamilton on one arm and Anna Sage on the other. According to some reports, Melvin Purvis shouted at Dillinger to surrender, and Dillinger reached into his pocket for a pistol and ran towards a nearby alleyway. According to other reports, the FBI, who had been instructed not to take any unnecessary risks, simply opened fire on Dillinger. Dillinger was hit four times, with two grazing wounds to his face, one bullet that passed through his upper chest near the collarbone, and one fatal bullet that entered the back of his neck, shattered his spine and exited under his right eye. He was dead when he hit the sidewalk.

According to press reports, a crowd of people gathered round and began dipping handkerchiefs and pieces of their skirts into the famed bank robber’s blood as a souvenir.

In the months after Dillinger’s death, his crime partner Baby Face Nelson was also ambushed by the FBI and killed. Anna Sage became infamous as “The Woman in Red”–and despite the agreement she had reached with the FBI, she was deported to Romania.

It seems that no famous outlaw is ever killed without silly conspiracy theories of the “it wasn’t really him” type appearing (Butch Cassidy, Billy the Kid, Jesse James, even Lee Harvey Oswald), and the same is true of John Dillinger.  Over the years conspiracy theorists opined that the man the FBI shot in front of the Biograph Theater that night was really a double (in some versions it is supposed to be a local hood named Jimmy Lawrence) to either fool the FBI and allow Dillinger to escape Chicago, or as a ruse for the government to place Dillinger into some sort of secret witness-protection program. There is no evidence at all for any of this, however.

An even more odd legend is that during the autopsy it was found that Dillinger had . . . uh . . . an impressively large male member, and it was removed and sent to the Smithsonian museum (or the Philadelphia Medical Society museum, depending on which version you believe), where it is kept pickled in a jar. There’s no evidence at all for that claim, either.

The Biograph Theater, where Dillinger met his fate, is now listed as a National Historic Landmark.


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