Ever since Alcatraz Federal Penitentiary opened as a maximum-security lockup in 1934 on a desolate island in the middle of San Francisco Bay, officials touted it as “America’s most secure prison.” During its nearly 30 years of operation, inmates put that reputation to the test with a litany of escape attempts ranging from the tame to the outrageous.
Over those three decades, the infamous prison known as “The Rock” housed more than 1,500 inmates, including some of the most notorious and dangerous men in America. In that span, 36 inmates tried to escape in 14 separate daring breakout attempts:
April 27, 1936: Joseph Bowers
Escape or suicide? Debate continues over how to classify the first-ever attempt to fly the Alcatraz coop. Joseph Bowers, called a loner and desperado by his fellow inmates (and described by some as criminally insane), was serving a 25-year sentence for mail robbery when, one afternoon while working at the trash incinerator, he tried to scale a fence on the island’s edge. After ignoring commands to stop climbing, Bowers was shot by guards after reaching the top of the fence, falling some 50 to 100 feet to his death
December 16, 1937: Theodore Cole and Ralph Roe
For their escape, Theodore Cole and Ralph Roe filed their way through flat-iron prison window bars and raced for the San Francisco Bay. Unfortunately for the two convicted Oklahoma bank robbers, their timing couldn’t have been worse. A particularly bad sea storm is believed to have swept Cole and Roe away to their deaths.
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May 23, 1938: Rufus Franklin, Thomas R. Limerick and James C. Lucas
First, this trio attacked prison guard Royal Cline with a hammer, inflicting fatal injuries. Then, as they attempted to overtake the prison’s guard tower, Limerick and Franklin were shot. Limerick died from his injuries. Lucas and Franklin, recaptured and charged with Cline’s murder, were both sentenced to death.
January 13, 1939: Arthur ‘Doc’ Barker, William Martin, Rufus McCain, Henri Young and Dale Stamphill
These five, led by Doc Barker of the infamous “Bloody Barker” gang, escaped from the isolation unit after sawing through their cell windows’ iron bars and leaping some 30 feet down onto the banks of the San Francisco Bay. They were swiftly met by armed correctional officers. Martin, Young and McCain surrendered, while Barker and Stamphill were shot when they refused to surrender. Barker died from his injuries.
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May 21, 1941: Joe Cretzer, Sam Shockley, Arnold Kyle, Lloyd Barkdoll
More hijacking than escape, the attempt of these four began and ended with the prisoners taking several of Alcatraz’s correction officers hostage—including Paul Madigan, who would become the penitentiary’s third warden. Madigan and the officers, however, gained the upper hand after convincing the robbers they’d never be able to escape after the prisoners failed to cut through Alcatraz’s “tool-resistant” bars.
September 15, 1941: John Richard Bayless
Bayless was out on garbage detail when he decided to make a run for it. But one hit of the frigid waters proved too much, as Bayless quickly reconsidered and gave up.
One failed attempt wasn’t enough to permanently deter Bayless, however. While appearing in court to appeal his sentence, he tried (unsuccessfully) to escape the courtroom.
April 14 1943: James Boarman, Harold Brest, Floyd Hamilton, Fred Hunter
These four inmates used prison-made knives to take two correctional officers hostage, binding and gagging them before escaping through a prison window and leaping into the San Francisco Bay. Before they got too far, however, one of the guards who’d been taken hostage escaped and raised the alert. While attempting to swim away, the four were fired at by Alcatraz guards. Hunter and Brest were apprehended. Boarman was shot in the water and his body was carried away by the current. Hamilton was believed to have drowned until he returned to the prison two days later after hiding in a nearby shoreline cave.
August 7, 1943: Huron Ted Walters
Huron Ted Walters was working in the prison’s laundry room when he made his break for freedom. But like many before him, he didn’t even make it to the water, being apprehended by officers at the shoreline.
July 31, 1945: John K. Giles
Technically speaking, John Giles did escape off the island. While a prisoner at Alcatraz, Giles’s job was to unload dirty army laundry from the loading dock to be cleaned at the penitentiary. One morning, at about 10:40 a.m., after spending several years piecing together a uniform resembling a U.S. Army technical sergeant, Giles calmly walked out of the prison and onto an army launch boat under the guise of being a military officer. Almost immediately, things went downhill. Officers on board the army vessel noticed they had one too many men while patrolmen at Alcatraz’s dock noticed one too few convicts. There was also the issue of Giles’s uniform—it fit badly and looked different from those of his “fellow officers” on board. By 11 a.m., he was apprehended and on his way back to the Rock.
May 2-4, 1946: Bernard Coy, Marvin Hubbard, Joseph Cretzer, Sam Shockley, Miran Thompson, and Clarence Carnes
The most famous escape attempt, remembered as “The Battle of Alcatraz,” resulted from a bloody, three-day standoff between prisoners and the guards. On May 2, six prisoners overpowered the cellhouse offices and gained access to the prison’s stash of weapons and ammunition. A promising start fell apart, however, after the prisoners realized they didn’t have the keys to the yard necessary to leave the prison. So instead of turning themselves in, the prisoners spent days battling against the officers. The standoff, which became so intense U.S. Marines were called in, left two officers dead and some 18 others injured. As for the prisoners? Coy, Cretzer and Hubbard were killed. In the aftermath, Shockley, Thompson and Carnes were charged with killing the two officers. They were sentenced to death and eventually executed by lethal gas while Carnes, who was 19, received a second life sentence.
READ MORE: 10 Things You May Not Know About Alcatraz
July 23, 1956: Floyd Wilson
Floyd Wilson disappeared from his job one morning while working as a stevedore on the Alcatraz dock. His sudden absence ignited a nearly 12-hour manhunt that eventually found the escapee hiding inside the depression of a rock along Alcatraz’s shore.
September 29, 1958: Aaron Burgett, Clyde Johnson
While working as garbage workers , robbers Burgett and Johsnon overpowered, bound and gagged an officer at knifepoint before attempting to swim from the island. The two were no match for the tides, however. Johnson was caught by officers while in the water and Burgett’s body was found floating in the bay two days later.
June 11, 1962: Frank Morris, John and Clarence Anglin
The only escape attempt with an uncertain ending. Brothers John and Clarence Anglin, along with Frank Morris, began their breakout with a bit of trickery: After tucking believable papier-mâché heads with real hair into their beds to fool nighttime guards, the trio used vent holes in the rear of their cells to access utility pipelines and gain access to the jail’s roof. From there, the escapees climbed down a drainpipe and made for the water, where they had makeshift life vests made out of jailhouse raincoats and a raft waiting for them.
From there they took to the rapids, never to be heard from again. Several weeks later a body dressed similarly to what the escapees were believed to have been wearing was found badly decomposed. Though the identity of the man was never confirmed, it was widely considered to be that of one of the convicts, with a similar fate assumed to have befallen the other three. Seventeen years later, the incredible escape was captured by Hollywood in the film Escape From Alcatraz starring Clint Eastwood
December 16, 1962: John Paul Scott, Darl Lee Parker
After bending the kitchen window bars in the jailhouse basement, Scott and Parker clambered out and made for the bay in an attempt to swim their way to freedom. Strong currents forced both activists to abandon their plans. Within hours, both were found clinging to outcroppings of rocks out in the Bay, unable to brave its tumultuous waters.