History

Famous Prison Breaks in History

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Updated:3/7/2026
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Prison Break
Prison
Year
Method
Known For
Escape from Alcatraz
Alcatraz Federal Penitentiary1962Dummy heads + raft from raincoatsFrank Morris + Anglin brothers, bodies never found, 'officially presumed drowned' but maybe not
The Great Escape
Stalag Luft III, Germany19443 tunnels (Tom, Dick, Harry)76 POWs escaped through tunnel 'Harry', 50 recaptured and executed, Steve McQueen movie
El Chapo's Tunnel Escape
Altiplano Prison, Mexico2015Mile-long motorcycle tunnelTunnel with motorcycle rail led to construction site, GPS-tracked him to the inch, second escape
Colditz Castle Escapes
Oflag IV-C, Germany1940-1945Various (hidden glider, uniforms)Nazi 'escape-proof' castle, 30+ successful escapes, POWs built a hidden glider in the attic
John Dillinger's Wooden Gun
Crown Point Jail, Indiana1934Fake gun carved from woodBluffed guards with a wooden gun darkened with shoe polish, stole the sheriff's car, folk hero
Pascal Payet's Helicopter Escapes
Multiple French prisons2001, 2003, 2007Helicopter extraction from roofEscaped by helicopter THREE times, also helped others escape, France had to ban helicopter flights near prisons
Papillon's Devil's Island Escape
Devil's Island, French Guiana1941Coconut-sack raft on ocean currentsHenri Charrière's memoir, shark-infested waters, Steve McQueen + Dustin Hoffman movie
Maze Prison Escape
HMP Maze, Northern Ireland1983Hijacked food truck + guns38 IRA prisoners escaped, largest prison break in UK history, guards taken hostage
Texas Seven
Connally Unit, Texas2000Overpowered guards, stole clothes7 inmates escaped together, America's Most Wanted led to capture, killed a police officer
Casanova's Venice Escape
The Leads (Palazzo Ducale), Venice1756Iron spike through ceilingGiacomo Casanova escaped Venice's infamous lead-roofed prison, wrote a book about it, legendary charm
Dannemora Prison Break
Clinton Correctional, New York2015Power tools + underground pipesTwo inmates seduced a prison worker for tools, 3-week manhunt, Ben Stiller directed the miniseries
Libby Prison Tunnel Escape
Libby Prison, Richmond, VA186457-foot tunnel109 Union officers escaped through tunnel, largest Civil War prison break, 48 recaptured
Yoshie Shiratori's 4 Escapes
4 different Japanese prisons1936-1947Miso soup on handcuffs, climbing wallsEscaped 4 prisons including Abashiri in winter, used miso soup to rust handcuffs, Japanese folk legend
Jack Sheppard's London Escapes
Newgate Prison, London1724Filed through chains, climbed chimneysEscaped 4 times, became 18th-century celebrity, public attended his execution, inspired Dickens
Billy Hayes' Midnight Express
Sagmalcilar Prison, Turkey1975Rowboat across Sea of MarmaraAmerican caught smuggling hashish, escaped Turkish prison, controversial 1978 movie, diplomatic incident

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