8 of the World’s Most Amazing Real-Life Prison Escapes (and What to Learn From Them)

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Photo: Iv-olga (Shutterstock)

Today, Alcatraz is a National Historic Landmark that functions as a tourist attraction, but back when it was a running prison, it was a beast—a seemingly inescapable jail on rocky island in the middle of the San Francisco Bay.

Back in 1962, three hardened criminals enacted probably the most famous prison escape in American history and made it off “The Rock.” Whether they made it to freedom or died in the attempt is an open question.

After months of silent preparation, on the night of June 11, 1962, four prisoners placed realistic heads sculpted of toilet paper and paste in their bunks, pulled the grates from the walls of their cells, slipped into the service corridor behind them, climbed a ventilation shaft to the prison roof, climbed down a drainpipe to the ground, scaled two razor-wire fences, traveled to the prison’s searchlight blindspot where they inflated a homemade raft they’d built, and paddled out into San Francisco Bay, never to be seen again.

The guards didn’t notice they were gone until the morning—the plaster heads bought them time—and after an extensive search in which the remains of their rafts and life jackets were found, the FBI concluded that the men most likely drowned. But family members of the escapees reported getting letters and postcards from them for years, and there were numerous other semi-credible but non-confirmed sightings of the men in the decades after their escape.

Lesson: You can’t overestimate the importance of planning ahead.

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