The Rise and Fall of America's Most Infamous Gangster Al Capone

From Brooklyn Streets to Chicago's Underworld

Born in 1899 in Brooklyn, New York, to poor immigrant parents, Al Capone went on to become the most infamous gangster in American history. His story is one of staggering ambition, brutal violence, and an almost theatrical downfall — brought low not by a rival bullet, but by a paper trail of unpaid taxes. Nearly eight decades after his death, Capone's life remains a defining chapter in the story of American crime.

In 1920, during the height of Prohibition, Capone's multi-million dollar Chicago operation in bootlegging, prostitution, and gambling dominated the organized crime scene. With a brash, flamboyant image and personal charisma that hid a murderous streak, he's believed to be responsible for the deaths of possibly up to 200 people, either directly or through The Outfit, his Chicago-based gang. He was flamboyant, always appearing in fancy suits and jewelry and smoking the finest cigars.

The Massacre That Changed Everything

The St. Valentine's Day Massacre on February 14, 1929, might be regarded as the culminating violence of the Chicago gang era, as seven members or associates of the "Bugs" Moran mob were machine-gunned against a garage wall by rivals posing as police. The audacity of the attack shocked the nation. Capone was never directly charged for it, but the public knew.

The Saint Valentine's Day Massacre, in which seven people from rival gangs were murdered in broad daylight, damaged the public image of Chicago and Capone, leading influential citizens to demand government action and newspapers to dub Capone "Public Enemy No. 1." In response to the public outcry, President Herbert Hoover ordered the federal government to step up its efforts to get Capone on income-tax evasion. The most powerful crime boss in America had finally overplayed his hand.

Brought Down by a Tax Bill

What finally brought down Public Enemy No. 1 wasn't murder, bootlegging, prostitution, or racketeering. It was tax evasion, which became a possibility after the Supreme Court ruled in 1927 that all income — legal or illegal — was subject to taxation. On June 5, 1931, the U.S. government finally indicted Capone on 22 counts of income-tax evasion.

On October 17, 1931, Al Capone was convicted of five counts of income tax evasion. The notorious Chicago gangster had been charged with evading taxes from 1924 to 1929. He was sentenced to 11 years in prison, fined $50,000, and ordered to pay $215,000 in back taxes. It was the harshest sentence delivered for tax fraud up to that point. The man who had outmaneuvered law enforcement for over a decade couldn't escape a ledger.

Alcatraz, Syphilis, and a Quiet End

In May 1932, 33-year-old Capone began his sentence at the U.S. penitentiary in Atlanta. Two years later, in August 1934, he and a group of fellow inmates were sent by train to California and then transported to the recently opened federal penitentiary on Alcatraz Island in San Francisco Bay. While at Alcatraz, Capone, who had been diagnosed with syphilis during a medical exam at the Atlanta penitentiary, started showing signs of the disease, including dementia.

Al Capone died of cardiac arrest in 1947, but his decline began earlier. After his transfer to Alcatraz, his mental and physical condition deteriorated from paresis, a late stage of syphilis. He was released in November 1939 and was sent to a Baltimore mental hospital before he retired to his Florida estate. The man once dubbed "Scarface" spent his final years largely diminished, a ghost of the empire he had built. His story remains a cautionary tale about the limits of power — and a reminder that even the most untouchable figures can be undone by the smallest of details.