On January 17, 1920, the United States passed the Volstead Act, federally outlawing the sale, manufacture and transportation of alcohol. But while booze may have been banned, notorious crime boss Al Capone saw an opportunity: Making a whole lot of money with a major bootlegging business.

Long before Capone gained infamy as Chicago’s most notorious prohibition-era gangster, he got his start in New York City. Born in Brooklyn to Italian immigrants, Capone was a smart child, albeit a troublemaker, taking on odd jobs throughout his community — and even enjoying a two-year stint in semi-professional baseball. Capone’s organized crime career began when he joined the James Street Boys gang and met legendary crime boss Johnny Torrio. The pair quickly built a rapport and in 1919, Torrio sent Capone to Chicago, tasking him with managing one of his brothels.

Not long after relocating to the Second City, prohibition hit, prompting Capone to launching a large-scale bootlegging business. Relying on both notably violent tactics as well as his friendships with local law enforcement and then-Chicago mayor, William Hale Thompson, Capone climbed the ranks, ultimately replacing Torrio as boss following his retirement. By 1930, Chicago’s Crime Commission named him as “Public Enemy Number One.”

Though rumors swirled that Capone’s weapon of choice was a baseball bat, a trope that appeared in pop culture during and long after his reign, experts say there’s no tangible evidence of this.

By this point, Capone had reached celebrity status and garnered reputation for loving women, outlandish outfits, cigars and all the finer things in life. As such, Capone was often asked about his line of work. He handled this questions like any good crime boss would. “I am just a businessman, giving the people what they want,” he once famously said.

With prohibition rumored to be coming to an end, Capone was looking for new ways to wet customers’ whistles and keep his business afloat. As such Capone decided to buy a dairy company. Using the company’s existing setup and tapping home delivery drivers rather than union workers to distribute the product, they were able to keep prices extremely low. After trying — and failing — to reach a deal with the dairy union leader, violence ensued, leading to smashed windows, shady deals and even a bombing.

On February 14, 1929, several men dressed as police officers opened fire on seven gangsters working under George “Bugs” Moran and Chicago’s Irish Mafia. 


While the details of what, exactly happened in the now-razed North Side garage are still largely unknown — “What we do know is seven men were gunned down that morning,” said John Russick of the Chicago History Museum — Capone is largely believed to be responsible for the attack. Three of the mobster’s associates were arrested in connection to the crime, but two were killed before they had their day in court.

Following the not-so-mysterious murders, Moran spoke to journalists about the massacre. “Only Capone kills like that,” he said days after the incident. Naturally, Capone fired back, famously stating that “the only man who kills like that is Bugs Moran."

By 1930, the Chicago Crime Commission reached out to then President Herbert Hoover to take down Capone, who was already being investigated for tax evasion.

Prohibition agent Eliot Ness was tasked with spearheading this investigation. As a part of the U.S. Treasury Department, Ness took down several illegal bootlegging operations, leading to millions in lost income for Capone. After allegedly turning down a bribe for $2,000 a week to overlook the Chicago crime boss’s operation, Ness earned both him and his team of agents the nickname of the “Untouchables.”

Though Capone had been arrested several times throughout his crime career, he plead guilty to tax evasion and 5,000 violations of the Volstead Act in 1931. That October, he was sentenced to 11 years in prison for the tax evasion charges.

After serving time at a prison in Atlanta, Capone arrived at San Francisco’s infamous Alcatraz prison in 1934. Known as Prisoner 85, Capone’s time behind bars was a lot more lax than his days running the Chicago mob. Described as a “model prisoner” by the History Channel, Capone spent his days reading, composing music and and completing his chores.

“Al Capone gets no more privileges than the rest, except that he does not get beaten or thrown into the dungeon,” an inmate told journalists. “He has too much political influence for that.”

But even with this new zen outlook on life, Capone still occasionally got in trouble, including an incident in which he hit a fellow prisoner in the head with a bedpan.

By the time Capone was released from jail in 1939, Capone’s untreated syphilis had made him incredibly sick, leaving him unable to reclaim his role as mob boss. He died on January 25, 1947, his death certificate denoting that he was “retired.”