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The Outlaw

June 2023
6min read

In 1933 Capone was in prison, his appeals exhausted. The nation had reached economic rock bottom. In March machinegun emplacements guarded Roosevelt’s inauguration as the Depression seemed to threaten the very foundation of government. In April John Dillinger walked out of an Indiana prison with five dollars and a new suit. A year later he would be known around the world.

Dillinger represented a breed that differed in fundamental respects from the gangsters who ruled Chicago. The history of the outlaw goes back at least to Jesse and Frank James, who robbed banks and trains on behalf of the Confederacy. The line runs through Butch Cassidy down to Charles Arthur (“Pretty Boy”) Floyd, the Barker gang, and other Depression-era bandits.

The gangsters grew up in urban settings and usually served apprenticeships with youth gangs. The outlaws were mostly of rural origin and lawabiding stock. A twist of fate, or sometimes a whim, propelled them into a criminal life. Gangsters pursued their ill-gotten gains through ongoing enterprises. Outlaws specialized in hitand-run crimes: robberies and kidnappings. They dreamed of a score, not a system. Gangsters rigorously kept their women at home, often hiding from them all the details of their illicit dealings. Outlaws’ women often joined in the fun. In some cases, as with Kate (“Ma”) Barker or George (“Machine Gun”) Kelly’s wife, Kathryn, they provided both the brains and the spunk.

John Dillinger epitomized the outlaw. He came from a respectable Indianapolis family that later moved to the more rural Mooresville, Indiana. Not an ambitious student, he was a good mechanic and so skilled at baseball that he dreamed of playing at Wrigley Field. In September of 1924, when Dillinger was twenty-one, an older friend induced him to rob a local grocer. They botched the holdup and were apprehended. John’s father, himself once a grocer, advised his son to plead guilty to this first offense and trust the court’s mercy. The judge, disgusted by brazenness of the crime, handed him ten to twenty years of hard time. During his nine years inside Dillinger went to school with experienced bank robbers. He emerged determined to extract payment for the patently unjust punishment.

During the summer of 1933 Dillinger visited Chicago for the first time and attended the gaudy Century of Progress, where he could gaze at what one newspaper called the “apotheosis of America’s womanly pulchritude” displaying itself in various states of undress. In the autumn he and his band pulled off successful robberies, hitting banks from rural Indiana to Racine, Wisconsin. They raided rural police stations for weapons and bulletproof vests. They escaped back to the anonymity of Chicago, where they occupied an apartment at 4310 Clarendon, still a quiet North Side neighborhood near Lincoln Park.

The newspapers of the day were on the lookout for spectacular stories that would distract readers from the dreary news of the Depression. Dillinger made headlines. His legend snowballed as even robberies he had no connection with were chalked up under his name.

In December, after one of Dillinger’s band shot a Chicago detective, the gang decamped for Florida. Wanderlust took them to Tucson, Arizona, where a portion of the gang, including Dillinger, was captured. In March of 1934 Dillinger used a wooden gun to pull off a spectacular escape from a heavily guarded jail in Crown Point, Indiana. The breakout startled the country and inflated Dillinger’s reputation a hundredfold.

Dillinger had taken up with a halfbreed Menominee Indian named Evelyn Frechette. After the escape they moved in with her sister Patsy, who had a second-floor apartment at 3512 North Halsted, two blocks from a police station. The building is still there. Note the side entrance that would have allowed an extra escape route.

He robbed more banks. On April 9, 1934, as the manhunt escalated, Dillinger almost walked into a trap. Federal men were waiting for him as he and Frechette drove up in front of a tavern at 416 North State Street. Evelyn had a bad feeling about the place. She went in to check. The government men grabbed her; Dillinger escaped. She never saw him again. Today the building houses a hot-dog emporium.

Taking a breather in northern Wisconsin, the Dillinger gang fought a gun battle with federal agents—the famous Little Bohemia shoot-out. The G-men killed an innocent bystander and lost one of their own. The incident particularly embarrassed the thirty-nine-year-old J. Edgar Hoover, head of the Justice Department’s Division of Investigation, soon to become the FBI. Hoover had assigned a special squad to hunt down Dillinger. For Hoover, Dillinger personified the wave of kidnappings and robberies sweeping the Midwest. During the Little Bohemia incident he prematurely announced Dillinger’s capture to the press.

The truth both outraged and disconcerted the public. The government appeared laughably ineffectual. Outlaws seemed to operate with impunity. In fact, a combination of elements beyond his own daring contributed to Dillinger’s success. He took advantage of the potential for speed that Detroit was increasingly engineering into its cars. He favored fleet eight-cylinder Fords and Hudson Terraplanes. Local law-enforcement officers rarely drove anything of comparable horsepower. They also lacked the mobile two-way radios that would later make hit-andrun robberies a much chancier option. To top it off, very little logistical or legal cooperation existed among various police forces, so that, in effect, crossing a state line conferred impunity.

The noose was tightening quickly around Dillinger during the summer of 1934. Some of his confederates were in prison; others considered it too dangerous to work with a man whose face was known to virtually everyone in the country. Though some of Dillinger’s robberies had netted as much as seventy thousand dollars, the expenses of living as a fugitive quickly ate into his bankroll. Plastic surgery failed to alter his looks convincingly. That June, in a publicity gimmick dreamed up by the crime fighters, the FBI designated him “Public Enemy Number 1.”

In July Dillinger was staying at 2420 Halsted, the apartment of Anna Sage, who would enter the history books as “The Lady in Red.” A former madam with ties to both the underworld and the police, Sage faced being returned to her native Romania. The vague promise of a reprieve from deportation, combined with the prospect of the fifteen-thousand-dollar reward then being offered, tempted her to turn informer.

She took her information to police officers she knew in East Chicago, Indiana. There’s always been speculation that those officers insisted on Dillinger’s death—either as revenge for another East Chicago policeman killed by him during a robbery in January or to cover the trail of bribery that led to the Crown Point escape. Dillinger’s only federal offense was his interstate transportation of a stolen car, a violation of the 1919 Dyer Act; bank robbery was not yet a federal crime. But it’s likely that the Chicago section of the FBI, headed by the dapper Southerner Melvin Purvis, conspired with the East Chicago detectives in Dillinger’s assassination.

Chicago had endured a fiveday heat wave. The temperature reached 108 degrees on Sunday, July 22, killing twenty-three people in the city. Dillinger had been staying with Sage for the past two days, along with his current lover, a waitress named Polly Hamilton. Sage informed the authorities that she and Polly would accompany John to see Manhattan Melodrama , a gangster movie starring Clark Gable, at the Biograph Theater on Lincoin Avenue, right around the corner from her apartment. In the basement of the Biograph electric fans blew on blocks of ice, and the air circulated to provide patrons with some relief from the swelter. While the movie played, sixteen federal agents and five East Chicago policemen surrounded the theater. The manager, fearful of a holdup, called the Chicago police, who knew nothing of the ambush. They were warned off by the G-men.

Though the Sage apartment is gone, movies are still shown at the Biograph, which stands at 2433 North Lincoln Avenue. The theater is the one Chicago crime site that has been added to the National Register of Historic Places. The original ticket booth, with its crown of light bulbs, is preserved in front.

Exiting the theater, Dillinger and the two women turned left. Sage wore a bright orange skirt as a signal (it appeared red under the lights). We can follow their steps along the hot sidewalk as they headed for the entrance to an alley a few doors to the south that leads back to Halsted. Before they reached it, the federal men closed in. Sensing danger, Dillinger ran toward the alley. He was shot four times. The fatal bullet pierced his back, exited below his eye. He fell facedown. Purvis rolled the corpse over with his toe. A crowd gathered. Women knelt to dip the hems of their slips in the blood, a memento of a wild time, a token of reality.

“We had a lot of fun,” Polly Hamilton would recollect. “It’s surprising how much fun we had.”

The outlaw era effectively ended in 1934. J. Edgar Hoover was still bragging about getting Dillinger thirty years later. Meanwhile, the gangsters who had made crime a business were looking at a bright future. The 1950 Kefauver hearings listed Capone men Tony Accardo, Jake Guzik, and Paul Ricca as mob powers and noted the expansion of the outfit into cities across the country’s midsection. In 1957 Sam Giancana, a onetime button man for Capone, bragged on a tapped phone line, “We got this territory locked up tight.”

The crimes that provoked outrage and revulsion seventy years ago are now safely wrapped in layers of myth and nostalgia. Today the young gangsters on Chicago’s streets, armed with weaponry that would have made Frank McErlane’s mouth water, refer to themselves as “Nitti” to advertise their facility with firearms. Gunfire still sounds in the streets, but few crime buffs venture into the lethal housing projects and gang territories to view the fresh gouges in the bricks.

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