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At 9:30 am on this day in 1934, no one thought to check the gun pointed at them.

It looked real enough. And the guards knew that the man holding it was capable of using it—he’d killed before. He’d escaped before, too.

But this gun had been whittled from wood and colored with shoe polish. And with it, one of the most infamous bank robbers in history, John Dillinger, walked out of a state-of-the-art “escape-proof” jail in Crown Point, Indiana, where he was being held for the murder of a police officer that had occurred during a January bank robbery in East Chicago, Indiana. (We called the Titanic “unsinkable,” we called this prison “escape-proof”; at some point we should stop tempting fate.)

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An Indiana native, Dillinger had spent most of his 20s in its prisons after a failed grocery store robbery. That was long enough to learn from fellow inmates how to do it better next time.

After his 1933 parole, he did. Dillinger robbed five banks in four months. He got caught in Ohio, but his gang broke him out. The law caught up with him again in Arizona, and he was sent back to Indiana to stand trial.

That led to his most theatrical escape, where he brandished the gun he’d carved, took hostages, and stole a sheriff’s car. He drove it to Chicago, which was the decision that changed everything: By crossing state lines in a stolen vehicle, he leveled up to a federal target.

The hunt was on.

Over the next few months, Dillinger slipped through everything. He robbed more banks. He robbed police stations. He escaped shoot-outs, dodged roadblocks, and altered his face with plastic surgery. He even tried to have his fingerprints removed.

After a series of increasingly violent encounters, including the death of a federal agent, the Bureau of Investigation named Dillinger Public Enemy Number One and put a reward on his arrest.

Fun Fact

Dillinger once eluded police by hiding in a haystack.

It all caught up with him outside a Chicago theater. The gun in his hand was real this time, but it didn’t make a difference. He was shot dead by federal agents, just four months after pulling off the most improbable escape in history.

By the Numbers
  • $300,000+: Total netted by Dillinger and his gang during their heists
  • At least 12: Banks robbed by Dillinger and his crew
  • 32: Days Dillinger spent in Crown Point’s escape-proof jail
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