John Dillinger

John Herbert Dillinger was a Depression-era American gangster who led the Dillinger Gang, a group accused of robbing two dozen banks and four police stations. He served multiple prison terms and managed to escape twice. Though charged with killing East Chicago police officer William O'Malley—who shot Dillinger in his bulletproof vest during a gunfight—he was never convicted; this was the only homicide charge he ever faced. Dillinger actively sought media attention, and newspapers played up his daring and colorful character, painting him as a kind of Robin Hood.

That publicity gave J. Edgar Hoover, head of the Bureau of Investigation, a reason to transform the BOI into the FBI, building up more advanced investigative methods to fight organized crime. After dodging police across four states for nearly a year, Dillinger was wounded in a shootout and recuperated at his father’s home. He later hid out in Charlevoix, Michigan. In July 1934, he returned to Chicago and took shelter in a brothel run by Ana Cumpănaș, who eventually tipped off authorities.

Family and background

On July 22, 1934, local and federal officers closed in on the Biograph Theater. As Dillinger left the theater, BOI agents moved to arrest him; he tried to flee and was shot dead. The use of lethal force was later ruled justifiable homicide. Dillinger was born on June 22, 1903, in Indianapolis, Indiana, the younger of two children of John Wilson Dillinger and Mary Ellen Lancaster.

His paternal grandfather, Mathias Dillinger, had emigrated from Prussia in 1854 to escape poverty and the draft. His parents married in 1887. His father, a grocer, was reportedly strict and believed in the adage “spare the rod and spoil the child.” Dillinger’s mother died in 1907, just before his fourth birthday. That same year, his older sister Audrey married Emmett Hancock and later cared for her brother until their father remarried in 1912 to Elizabeth Fields, with whom he had three more children.

As a teen, Dillinger often fought, stole, and bullied smaller kids. He left school to work in a machine shop. Worried the city was a bad influence, his father moved the family to Mooresville, Indiana, in 1921. But Dillinger’s wild behavior continued.

Formative years and marriage

In 1922, he was arrested for auto theft, straining his relationship with his father. In 1923, he joined the Navy, serving as a petty officer repairing machinery on the USS Utah. He deserted a few months later while docked in Boston and was dishonorably discharged. Back in Mooresville, he met Beryl Ethel Hovious, and they married in April 1924.

Hard up for work, Dillinger planned a robbery with his friend Ed Singleton. Hovious divorced him in June 1929 while he was in prison—a blow Dillinger said broke his heart and pushed him further into crime. The pair robbed a grocery store, stealing about $50. During the heist, Dillinger hit a victim with a cloth-wrapped machine bolt; his gun fired but hit no one.

A minister who knew them spotted them fleeing and tipped off police. They were arrested the next day. Singleton pleaded not guilty, but Dillinger’s father—a local deacon—convinced him to confess and plead guilty without a lawyer, after talking with the prosecutor. Dillinger expected probation but got ten to twenty years.

His father later said he regretted the advice and begged the judge for a shorter sentence, to no avail. On his way to testify against Singleton, Dillinger briefly escaped but was caught quickly. Singleton got two to fourteen years and died in 1937 after falling asleep drunk on railroad tracks. While locked up from 1924 to 1933, Dillinger turned to a life of crime.

Prison time

Upon entering prison, he reportedly vowed to become “the meanest bastard” anyone had ever seen. A physical exam revealed he had gonorrhea, and the painful treatment left him bitter. He befriended seasoned bank robbers like Harry Pierpont, Charles Makley, Russell Clark, and Homer Van Meter, who taught him the ropes. Together, they planned future heists.