
In January of 1934, John Dillinger was arrested in Arizona and extradited to Indiana, where he was lodged ion the Lake County Jail at Crown Point. The jail had a reputation as being extraordinarily secure. Another notable fact was that Lake County, which operated the jail, had a woman sheriff, which was quite rare at the time. Extra personnel were assigned to Dillinger. A few weeks later, he made his escape.
Dillinger pressed a gun into the back of a trustee, who became his hostage. Dillinger then locked the guards in a cell and took possession of their machine guns, and escaped in the sheriff's car. Dillinger was on the loose for 141 days before he was killed by federal agents outside a movie theater in Chicago. So how did he pull of the jailbreak? The "gun" he initially used turned out to be carved from wood, but we don't know if Dillinger made it himself. He had to have help, at least with arranging for the sheriff's car to be available. There were plenty of suspects, but no one was ever convicted of helping in the escape. Read what we know about Dillinger's jailbreak at Utterly Amusing.
(Image credit: U.S. National Archives and Records Administration)


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