Top Image: Inset – Mug shot of Al Capone. Main: The prison cell of Al Capone at Eastern State Penitentiary.

Al Capone was a notorious American gangster whose multi-million dollar Chicago operation in bootlegging, prostitution, and gambling dominated the organized crime scene for nearly a decade. At the height of his power, he employed over 1,000 gunmen in his service and had up to half of the city’s police force on his payroll. Yet in his final years, he had descended into a frightened, quivering mess, who would scream out at night for ‘Jimmy’ to leave him alone. Did Al Capone suffer mental illness in his final years, or was he haunted by one his hapless victims?

Alphonse Gabriel "Al" Capone (1899 – 1947) was born in Brooklyn, New York, the son of recent Italian immigrants. His entrance into a life of crime began when he moved to Chicago and became a friend and bodyguard to Johnny Torrio, head of a criminal syndicate that illegally supplied alcohol during America’s Prohibition era.

Al Capone is shown here in 1930 at the Chicago Detective bureau following his arrest on a vagrancy charge.

It was not long before Al Capone had adopted the life of a dangerous gangster. By the age of 26, he was a powerful crime boss who had both political and law-enforcement protection. He used bribery and widespread intimidation to influence elections, and violence and murder to ensure his business in illegal breweries was a success. Capone was left virtually untouched by the law until the brutal Saint Valentine’s Day Massacre of gang rivals, which led influential citizens to demand government action.

Saint Valentine’s Day Massacre

By early 1929, Capone dominated the illegal liquor trade in Chicago. But other racketeers, known as the North Side Gang, vied for a piece of the profitable bootlegging business, and among them was Capone’s long-time rival “Bugs” Moran. Capone decided that Moran was too big of a threat and had to go.

On the morning of February 14, 1929, Capone’s men, posing as police, launched a fake raid on the North Side Gang. The faux police lined 7 men along a wall and then mowed them down with machine guns. Alerted to the danger ahead of time, Bugs Moran escaped the slaughter. Photos of the victims shocked the public and damaged Capone’s reputation among his political allies, and a decision was made to finally act on Capone’s lawlessness.

The photo of the Saint Valentine’s Day Massacre finally forced law enforcement to act against Al Capone.

Without proof to tie him to the massacre, Capone had to be brought in on other charges. In May 1929, Capone was arrested for carrying a gun during a trip to Philadelphia and was sentenced to a prison term in Philadelphia’s Eastern State Penitentiary.

Al Capone Tormented by ‘Jimmy’

Al Capone’s connections ensured he was given top treatment in prison. While other prisoners suffered in bare, concrete cells with a simple slab for a bed, Capone’s cell was adorned with fine furniture, oil paintings, and a radio. But his ‘luxurious’ cell, did little to make Capone’s stay a comfortable one – it was not long before the rough and tough crime boss had transformed into a weeping and terrified mess who would send out blood-curdling screams at night, shouting for ‘Jimmy’ to leave him alone.

Left: A regular cell at Eastern State Penitentiary. Right: Al Capone’s cell.

Many people believe that ‘Jimmy’ was the ghost of one of Al Capone’s victims, who would torment him night after night. Indeed, one of the seven victims from the Saint Valentine’s Day Massacre was named James (“Jimmy”) Clark. Originally born Albert Kachellek, Jimmy was Bugs Moran’s brother-in-law, and died on that bloody February 14.

The torment followed Capone after he left Eastern State Penitentiary and went on to serve another 11 years at Atlanta US Penitentiary and Alcatraz for tax evasion. In 1931, Capone even called in a medium, named Alice Britt, to try to find out what Jimmy wanted. Apparently, Britt was unsuccessful and Capone continued to be terrorized.

Others point to a more scientific explanation for his torment.

Syphilis Claims the Mind of Al Capone

At about 20 years of age, Capone worked as a bouncer in a brothel, where he contracted syphilis. He never sought treatment, which caused the disease to advance into neurosyphilis, leading to dementia. After serving six-and-a-half years in prison, Capone was released in 1939 to a mental hospital in Baltimore, where he remained for three years.

Al Capone’s health deteriorated, and by 1946 his physician and a Baltimore psychiatrist performed examinations and concluded Capone had the mental capacity of a 12-year-old child. On January 25, 1947, Capone died of cardiac arrest. He was buried at Mount Carmel Cemetery in Hillside, Illinois.

The grave of Al Capone in Hillside, Illinois.

No one really knows why Capone would incessantly call out ‘Jimmy’ in his final years. While many are convinced it was the ghost of his hapless victim, James Clark, others maintain that it was the guilt for his crimes combined with declining mental health that led to his torment by the unknown Jimmy, who remained with him until his final days.