John Herbert Dillinger joins the Navy in order to avoid charges of auto theft in Indiana, marking the beginning of America’s most notorious criminal’s downfall. Years later, Dillinger’s reputation was forged in a single 12-month period, during which he robbed more banks than Jesse James did in 15 years and became the most wanted fugitive in the nation.
Dillinger didn’t last in the Navy very long. Within months he had gone AWOL several times–the last time in December 1923. Making his way back to Indiana, he was arrested for armed robbery the following summer. Dillinger pled guilty, thinking that he would receive a light sentence, but instead got 10 to 20 years. His first words to the warden at the prison were, “I won’t cause you any trouble except to escape.” A man of his word, Dillinger had attempted to escape three times by the end of the year.
Between escape attempts, Dillinger became friendly with some of the more professional thieves in the prison. After he was finally paroled in May 1933, Dillinger hooked up with his new friends and began robbing banks throughout the Midwest. He also began planning to break his friends out of prison. In September, he smuggled guns in to Harry Pierpont, who led a 10-man break from the Michigan City prison.
In 1933, Dillinger’s assistance turned out to be fortuitous because as his friends were breaking out, Dillinger himself was captured and arrested for bank robbery in Dayton, Ohio, and then imprisoned in Lima, Ohio. Pierpont and the others returned the favor and broke Dillinger out in October, killing a sheriff in the process. The gang was now in full force. A week later, they raided a police arsenal in Peru, Indiana. The arrogant bandits pretended to be tourists who wanted to see what weapons the police were going to use to capture the Dillinger gang.
Given the remarkable string of armed robberies and acts of violence in such a short period of time, police departments throughout the Midwest set up special units to capture Dillinger. Ironically, his eventual arrest was the result of pure luck. While hiding out in Tucson, Arizona, Dillinger was caught in a fire that broke out in his hotel. Firefighters became suspicious when they were offered a large sum of money to save two heavy suitcases. When they found a small arsenal of guns inside, those involved, including Dillinger, were taken into custody.
Dillinger was extradited to Indiana and held in what was believed to be an escape-proof jail, with extra guards posted to protect against outside attacks. But on March 3, 1934, Dillinger used a fake pistol that he had carved out of wood and painted black to escape. For the next several months, Dillinger and his gang went on a bank-robbing spree with the FBI one step behind at all times. J. Edgar Hoover, the director of the FBI, reportedly put out an order that agents should shoot Dillinger on sight. An immigrant named Anna Sage offered to set the outlaw up if deportation proceedings against her for operating a brothel were dropped. On this same day—July 22—in 1934, FBI agents Charles B. Winstead, Clarence O. Hurt and Herman E. Hollis fired at Dillinger as he was leaving the Biograph Theater in Chicago, Illinois.
Some historians believe that the man killed that day was not Dillinger, and that Dillinger may have engineered the setup to drop out of sight. If so, he was successful—no further record of Dillinger exists.
