11 Of History’s Most Daring Prison Escapes And The Heart-Pounding Stories Behind Them

Published December 1, 2021

John Dillinger’s Prison Escape

John Dillinger Prison Escape

FBIJohn Dillinger robbed dozens of banks before he was killed in Chicago.

His name alone sparks imagery of Tommy Guns, trench coats, and the heyday of organized crime. Born in Indianapolis in 1903, John Dillinger would certainly earn that association during the Great Depression. Before he died in 1934, Dillinger had robbed 24 banks and been imprisoned several times — and once had ingeniously escaped.

A high school dropout, Dillinger began his life of crime by shoplifting and stealing cars. He served in the Navy before being discharged and married a 16-year-old in 1924. Realizing he couldn’t provide for her, he robbed a store owner and served nine years in prison. Divorced upon his release on May 10, 1933, Dillinger began robbing banks for a living.

The 29-year-old formed a crew with Paul Parker, William Shaw, and Noble Claycomb and robbed upwards of $30,000 from various banks before being arrested in Ohio. While Dillinger provided his men with a blueprint to escape and break him out, his most infamous jailbreak came in 1934.

Biograph Theater

FBIThe Biographer Theater in Chicago, Illinois, where FBI agents gunned John Dillinger down on July 22, 1934.

By shooting a prison guard and breaking Dillinger out of prison, the men had committed an interstate felony as soon as they crossed the border into Indiana. That led FBI director J. Edgar Hoover to wield the agency at Dillinger — who was arrested in Tucson, Arizona in January 1934 and extradited to Crown Point, Indiana.

“I know he’s a bad baby and a jailbreaker but I can handle him,” said Sheriff Lillian Holley.

Sheriff Holley was confident that Crown Point jail would keep Dillinger behind bars and even boasted that it was escape-proof. But, rather than await trial for the murder of a police officer, Dillinger spent his time whittling a wooden gun — which he used to fool the guards into opening his cell with on March 3, 1934.

After grabbing two machine guns, he imprisoned the guards themselves and fled Crown Point in Sheriff Holley’s car. With a nationwide manhunt in place as a result, Dillinger would be located and gunned down within months. Unfortunately for Sheriff Holley, the bank robber’s death on July 22 robbed him of revenge.

“If I ever see John Dillinger, I’ll shoot him with my own pistol,” he said. “This is too ridiculous to talk about.”

author
Marco Margaritoff
author
A former staff writer for All That’s Interesting, Marco Margaritoff holds dual Bachelor's degrees from Pace University and a Master's in journalism from New York University. He has published work at People, VICE, Complex, and serves as a staff reporter at HuffPost.
editor
Adam Farley
editor
Adam Farley is an Assistant Editor at All That's Interesting. He was previously content director of ShamrockGift.com and deputy editor of Irish America magazine. He holds an M.A. from New York University and a B.A. from the University of Washington.