Alcatraz isn’t just a rock in the San Francisco Bay. It’s a fortress. For some a nightmare, a warning to the worst of the worst.
Opened as a federal prison in 1934, it was designed to break the spirits of the country’s most dangerous criminals.
Surrounded by freezing waters and fortified with steel bars and gun towers, escape was a fantasy — but some still tried.
Here are 10 of the most infamous men to ever walk The Rock’s echoing corridors.
Al Capone — Public Enemy No. 1
America’s most notorious gangster. Capone ran Chicago’s underworld through bootlegging, bribery, and blood. At Alcatraz, he was stripped of power, cut off from his criminal empire, and forced to face his own paranoia and syphilitic decline. He left the island broken — a shadow of the kingpin he once was.
George “Machine Gun” Kelly — The OG Celebrity Gangster
Not the rapper. The original Machine Gun Kelly was a bank robber, kidnapper, and headline magnet. Known for his bravado, Kelly famously begged guards for protection from other inmates. He spent 17 years at Alcatraz, the longest of any prisoner.
Robert Stroud — The Birdman of Alcatraz
Despite the nickname, Stroud never kept birds at Alcatraz. He was a brutal, calculating killer known for his temper. His life was mythologized by Hollywood, but the real Stroud was a violent sociopath who spent 42 years in solitary confinement.
Alvin “Creepy” Karpis — Public Enemy No. 1 (Again)
Karpis, the last of the FBI’s “Public Enemy” targets, was a cunning criminal with a permanent sneer. He ran with the Barker gang, terrorizing the Midwest, and was once considered too dangerous for any prison but Alcatraz.
Roy Gardner — The Smiling Bandit
Gardner pulled off train heists and bank robberies with a grin. He escaped multiple prisons before Alcatraz finally broke him. Known for his charisma and sharp mind, Gardner was one of the few who nearly slipped the Rock’s iron grip.
James “Whitey” Bulger — The Real-Life Mob King
Decades before his capture in 2011, Bulger served time at Alcatraz for armed robbery and hijacking. He would later become one of Boston’s most feared mob bosses, evading the FBI for 16 years.
Arthur “Doc” Barker — Son of a Notorious Crime Family
Part of the Barker-Karpis gang, Doc was as ruthless as his mother, Ma Barker. He died in an escape attempt, shot down in the foggy waters off Alcatraz’s shore.
Frank Morris — The Mastermind
Morris, along with brothers John and Clarence Anglin, pulled off the most famous escape attempt in Alcatraz’s history. They vanished into the dark waters of the Bay in 1962, leaving behind dummy heads in their beds. They were never found.
Henri Young — The Killer Who Inspired a Movie
Young’s violent 1939 escape attempt ended in murder, leading to his portrayal in the film Murder in the First. His case highlighted the brutal conditions at Alcatraz and fueled the prison’s eventual closure.
Joseph “Dutch” Bowers — The First to Try
Bowers made the first known escape attempt in 1936, trying to scale a fence in broad daylight. He was shot dead by guards, his body crumpling at the island’s edge — a grim warning to those who came after him.
Alcatraz closed its cell doors for good in 1963, its legend cemented in blood and iron. Today, it’s a tourist trap, but the ghosts of men like Capone and Morris still cling to its rusting bars and cracking concrete.
