One of Alcatraz’s most infamous prisoners left The Rock on this day in 1939

One of Alcatraz’s most well-known prisoners left the famed island penitentiary in San Francisco Bay for the last time 87 years ago today on Jan. 6, 1939, for medical reasons.

Eight years later, former gangster Al Capone, also known as “Scarface,” would die of his ailments in seclusion at his Florida mansion.

Here’s his story:

The rise and fall of Al Capone

Capone, born in Brooklyn, New York, in 1899, gained the nickname “Scarface” after being slashed in the face at age 18 by the brother of a woman he was harassing in a bar, HowStuffWorks said. The injury required 80 stitches to close.

He hated the nickname and tried to hide the scar in photos, TheCollector said.

Capone moved to Chicago in 1920 to join a crime racket run by a friend from a New York street gang, the FBI said. The gangsters grew powerful running liquor during Prohibition.

In 1925, Capone took over as boss when his friend, Johnny Torrio, retired after being injured in a failed assassination, the FBI said.

On Feb. 14, 1929, Capone’s gang reportedly carried out the St. Valentine’s Day Massacre, gunning down seven gangsters from a rival mob, the FBI said. Capone himself was in Florida at the time.

In 1931, Capone was famously convicted on tax evasion charges and sentenced to 11 years in federal prison, according to the FBI.

He served the first part of his sentence in an Atlanta, Georgia, prison before being transferred to Alcatraz in 1934, a few weeks after the prison opened.

Al Capone’s life on Alcatraz

Designated as Prisoner No. 85, he became something of a model prisoner at the island prison in San Francisco Bay, History.com said. He spent his days as a “serious reader, a musician and a composer.”

Despite his career as a mobster, Capone hardly qualified to be sent to Alcatraz, designed as an escape-proof penitentiary for the worst of the worst, the site said. But he was most likely transferred there to help publicize the new penitentiary, nicknamed The Rock.

Capone was assigned a 9-foot-by-5-foot cell and, unlike other prison stays in which he enjoyed home-cooked meals and silk underwear, received no special privileges at Alcatraz, History.com said.

He lobbied the warden for a year for permission to start a musical band, in which he played the banjo and mandola, a kind of mandolin, the site said.

Bank robber George “Machine Gun” Kelly played drums in the band. But Capone never crossed paths with another famous inmate, Robert Stroud, dubbed the “Birdman of Alcatraz” although he kept no birds there, who came to the island in 1942.

In 1936, a fellow prisoner attacked Capone with a pair of scissors as he mopped the showers, but Capone reportedly smashed him over the head with his mandola.

Capone’s untreated syphilis began to send him into what was then referred to as syphilitic insanity — now known as paralytic dementia, History.com said. The National Institute of Neurological Disorders and Stroke said paralytic dementia symptoms can include delusions along with memory and language problems. He was transferred off The Rock after four years there on Jan. 6, 1939.

The last days of Al Capone

Capone finished out his prison sentence at penitentiaries in Los Angeles and Lewisburg, Pennsylvania, History.com said. His original 11-year sentence was shortened for good behavior.

On his release from prison later in 1939, Capone spent some time at a mental hospital before retiring to his Palm Island, Florida, mansion, where he lived quietly with his family, A&E reported.

Capone’s physical and mental health continued to decline, the site said.

Doctors said the once-infamous mobster had the “cognitive processes of a 12-year-old child,” The Mob Museum said.

He had a stroke in January 1947 and died quietly of cardiac arrest while surrounded by his family at age 48 on Jan. 25, A&E said.

Alcatraz closed in 1963, mainly as a result of the high cost of operating the island prison, which had to be supplied by boat with everything, even fresh water, PBS said.

It reopened as a national park in 1973, receiving about 1.2 million visitors a year, the National Park Service said.

In recent months, President Donald Trump has proposed reopening Alcatraz as a prison.

This story was originally published January 6, 2026 at 5:00 AM with the headline "One of Alcatraz’s most infamous prisoners left The Rock on this day in 1939."