The Most Impressive Prison Escapes of All Time

Wood and Shoe Polish

On March 3, 1934, Dillinger and another inmate used a fake gun to break out of the facility. A true gangster, Dillinger used the sheriff’s brand-new V-8 Ford as his getaway car. To this day, there is still debate about exactly what the gun was made of, and how the escape actually happened. But most people believe that he used a wooden gun that he then painted black with shoe polish.

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John Dillinger with his prosecuting attorney, Robert Estill, and Sheriff Lillian Holley, his jailer. Photo by Everett Collection / Shutterstock

The prison guards, fooled by the gun and fearful of the gangster, allowed Dillinger to leave the prison. While on the run, Dillinger made the most of his “free time.” America’s “Public Enemy #1” went on a yearlong crime spree across the Midwest, robbing a dozen or so banks and police stations.

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