Over the years, I have heard of people being told that they had just two choices following a crime…jail or the military. I don’t know if that was the choice given to John Herbert Dillinger, or if her just decided to use the Navy as a way “out of town” to escape his woes, but on this day, that is exactly what Dillinger di…joined the Navy in order to avoid charges of auto theft in Indiana. This would not be a moment of “change” for one of America’s most notorious criminals, but it would rather prove to be his 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.
While he tried to escape his troubles in that way, Dillinger didn’t last in the Navy very long either. Within months, he had gone AWOL several times, the last in December 1923. Back in Indiana, he was arrested for armed robbery the following summer. Dillinger pled guilty, expecting a light sentence, but was instead given 10 to 20 years. His first words to the prison warden were, “I won’t cause you any trouble except to escape.” True to his word,
Dillinger had tried to escape three times by the end of that year. While serving time and plotting escapes, Dillinger befriended some of the more seasoned thieves in prison. As it turns out, very few people are truly rehabilitated in prison. After his parole in May 1933, he teamed up with these new allies and started robbing banks across the Midwest. He also hatched a plan to free them from prison. In September, he smuggled guns to Harry Pierpont, who went on to lead a 10-man breakout from Michigan City prison.
In 1933, Dillinger’s help proved unexpectedly lucky, as while his friends were breaking out, he was caught and arrested for a bank robbery in Dayton, Ohio, and sent to prison in Lima. Pierpont and the others soon repaid the favor, breaking him out in October and killing a sheriff in the process. With the gang back together, they were at full strength. Just a week later, they hit a police arsenal in Peru, Indiana, posing as curious tourists eager to
see the weapons meant to capture them. You might think Dillinger would’ve laid low after his escape, but he was bold, carrying on his crime spree by robbing banks and getting into shootouts with law enforcement. His breakout sparked a nationwide manhunt, ending when FBI agents tracked him down and killed him on July 22, 1934, outside Chicago’s Biograph Theater.

