ALCATRAZ’S MOST DANGEROUS INMATES

An official public enemy number one and part of a formidable 1930s crime gang of robbers, hijackers, and kidnappers – Karpis was the group’s leader with a photographic memory.
Legend says he was captured by FBI director J. Edgar Hoover himself and sentenced to life imprisonment at Alcatraz for ten murders, six kidnappings, and a robbery.
He was the last of the depression-era criminals to be caught and served the longest sentence, 26 years, of any Alcatraz prisoner. Alvin and Arthur Barker, another member of the gang, were at Alcatraz and a part of the infamous breakout, during which Alvin was shot and killed. 

Al Capone was involved in crime from a young age and later became an infamous gangster and criminal mastermind. At the same time, he had political connections and was known for helping the poor and needy. However, public opinion turned against him after the St. Valentine’s Day Massacre and his capture became a priority for the new President Hoover. Five years later he was sent to Atlanta Jail where he manipulated the system, bribing the guards to receive home comforts. He was later transferred to Alcatraz where he led a very different and harsher existence. 

A prohibition gangster, Kelly became a bootlegger in an effort to avoid financial hardship. He then met and fell in love with another outlaw, Kathryn Thorne, and under her influence he became increasingly notorious and earned his ‘Machine Gun’ nickname.  His downfall was the kidnap and ransom of an oil tycoon, for which he and other gang members received life sentences. When he was sent to prison, he told the press that he would escape and break out his wife in time for Christmas. The authorities took him seriously, but he was sent to Alcatraz instead. He didn’t make it home for Christmas. 

Robert Stroud, the Birdman of Alcatraz, was surely the prison’s most famous inmate. He even had a film made about him, which earned Burt Lancaster an Oscar nomination. Stroud was imprisoned for murdering a bartender who had allegedly owed money to a prostitute that Stroud was pimping. When jailed, he was a violent prisoner, eventually stabbing a prison guard. He was put into solitary confinement where he developed an interest in canaries, having found one injured on the prison grounds. He later bred and studied them, eventually publishing books on the subject. He found his way to Alcatraz after guards from his previous prison found some of his ornithological equipment was being used to brew alcohol. He spent 17 years there – six in segregation – without his birds, spending his time writing and illustrating books.  

Roy Gardner, a charismatic and adventurous figure, led a life marked by a series of criminal exploits and daring escapes. Starting as a gunrunner during the Mexican Revolution, Gardner’s criminal career took off when he robbed a U.S. Mail truck in 1920, amassing a substantial fortune. Despite being captured and sentenced to prison, Gardner repeatedly managed to escape, including one audacious escape by overpowering his guards on a moving train. The subsequent manhunt made him one of the most wanted criminals on the Pacific Coast. However, Gardner’s life of crime eventually caught up with him, leading to his recapture and imprisonment in Leavenworth and later Alcatraz. He would describe Alcatraz as “the toughest, hardest place in the world.” He was released in 1939 on parole. In 1940, in a tragic turn of events, Gardner took his own life in a San Francisco hotel room.

Following a life of crime sprees, Frank Morris was transferred to Alcatraz in 1960. He began plotting his escape with four others. They stole tools, which they used to dig out. They built a raft and dummies for their cell beds. They escaped on June 11, 1962, and although the raft and some personal items were found, the men never were. It was presumed that they had drowned in the strong current, but no bodies were ever found. So, no one is really sure whether the group escaped or died trying. 

Arthur ‘Doc’ Barker, in collaboration with his brother, engaged in a series of criminal activities, including murder, kidnapping, and robbery. However, his time at Alcatraz was cut short when he met his demise during a daring escape attempt. Barker’s story serves as a reminder of the dangerous lengths some inmates were willing to go to regain their freedom.

James ‘Whitey’ Bulger started out his criminal career with armed robbery. He was sent to the Atlanta Penitentiary and while he was there he volunteered for a CIA experimental program and was given LSD amongst other harmful drugs. When it was found out that he was planning a prison escape in 1959, he was sent to Alcatraz. Following his release from prison in 1965 he was convicted of a total of 11 murders and was sent to the Florida Coleman Penitentiary to serve out 2 life sentences.

These brothers were both sent to Alcatraz following a bank robbery and attempted escapes from other prisons. Once there, they planned an escape and used spoons and saw blades to burrow into the cement near the back of their cells. They constructed a raft using raincoats and on June 11, 1962, the brothers along with fellow inmate Frank Morris made their way to the bay. This is the last place they were seen. While it’s unlikely that they survived the frigid cold weather of the water, there are legends of their escape survival even today.