Alphonse Gabriel “Al” Capone – From Obscurity to Chicago Outfit Boss

Alphonse Gabriel “Scarface” Capone led Chicago’s Mafia during its Prohibition heyday, rising from obscurity as a Brooklyn tough to become the best-known mobster in America. Capone’s empire encompassed illegal liquor, gambling and prostitution in Chicago during the 1920s. He reaped a reputation among many as the most violent man in the country while convincing others he was just a businessman supplying a service to a thirsty public.

Hundreds of people were killed on his orders, and he murdered several himself, but he was never convicted of a violent crime. In the end he was sent away for tax evasion. By the time he got out, he had gone insane and the world of organized crime had passed him by. But he died leaving a legacy of mayhem that has yet to be surpassed.

Al Capone was born in Brooklyn on January 17, 1899, to Italian immigrants Gabriele and Teresina Capone. His father cut hair for a living; his mother sewed. While two of his brothers went on to join him in bootlegging, a third became a federal agent.

After hitting a teacher, Capone was expelled from school at 14. For a time he ran with small-time gangs such as the Bowery Boys and the Junior Forty Thieves, then moved up to the notorious Five Points Gang that controlled criminal activity in Lower Manhattan. He soon fell under the eye of Giovanni “Papa Johnny” Torrio, owner of a Brooklyn billiards hall and leader of a criminal syndicate involved in gambling, prostitution and opium trafficking.

In 1917 Capone was hired as a bartender at the Harvard Inn, a Coney Island tavern owned by Torrio’s partner, Frankie Yale. It was there that Capone earned his famous nickname: He made a lewd pass at a woman, and her brother cut him three times across the left side of his face. Fellow hoods took to calling him “Scarface,” though not in his presence.

While working for Yale the next year, Capone got into a fight with another gangster that led to tensions in the Brooklyn underworld. He also became a suspect in a murder investigation. To protect him, Yale sent him to Chicago, where Torrio had joined his uncle by marriage, mob boss Giacomo “Big Jim” Colosimo.

Prohibition arrived in 1919 and provided a golden opportunity for the so-called Chicago Outfit, that city’s branch of the American Mafia. The city is centrally located, with ample water and rail access, and it made the perfect centerpiece of a bootlegging empire.

But Colosimo didn’t want to expand, so Torrio had him killed. Yale and Capone have each been considered suspects. With Colosimo gone, Torrio took over the Outfit, and Capone rose to prominence within its ranks.

 

Throughout the early 1920s, Capone and Torrio built a powerful liquor business centered on the South Side and the neighboring town of Cicero. They competed primarily against the North Side Gang led by Irish-American mobster Dean O’Banion. Capone quickly built a corrupt political machine to back him, laying siege to Cicero, where he rigged elections and installed a puppet government in 1924.

That year, O’Banion, learning one of his breweries was about to be raided, sold it to Torrio. Torrio ended up in jail and vowed revenge. He got it: O’Banion was gunned down in his flower shop a few months later. All-out war followed, and Capone reaped the rewards.

O’Banion’s men tried to assassinate Torrio but failed. The experience convinced him he’d had enough, and he quit, handing the reins to Capone.

Capone now had his hands on a racketeering empire that pulled in $100 million a year. Revenue came from gambling, prostitution and extortion, but mostly from booze. This enterprise required political corruption on a massive scale and fueled street violence so frequent it became routine.

Capone funneled regular bribes to Chicago Mayor William “Big Bill” Thompson, who ran the city from 1917 to 1923 and 1927 to 1931. Capone also had police officers, judges and other public figures in his pocket. Chicago elected a reform mayor in 1923, and crime dropped, but even that barely put a dent in Capone’s operations before Thompson returned.

As a result of the Outfit’s free reign, violence blossomed. Scores of people died in gun battles and executions, while the mob used beatings and bombings to intimidate competitors, businessmen, witnesses and jurors. Capone’s organization continued to battle the North Side Gang, now run by George “Bugs” Moran. Moran tried to kill Capone more than once but never hit him.

The violence reached a head in February 1929 in a garage at 2122 North Clark Street. The backlash it created finally brought Capone to his knees.

Moran and his men had recently killed two of Capone’s top mobsters and were muscling in on Outfit territory. In retaliation, Capone sent gunmen dressed as cops to the garage, where they expected to find Moran. The assassins announced a “raid,” lined seven North Side men against a wall, and shot them to pieces. But Moran, who was running late, missed his own execution.

Newspapers published gruesome photos of the scene, and the public demanded justice. Capone, who had long tried to cover his violent ways by cultivating a reputation as a simple businessman meeting a public demand for alcohol, had gone a step too far.

No one was ever tried for the “St. Valentine’s Day Massacre,” but the outcry fueled a growing effort to prosecute Capone. He was arrested in Philadelphia in 1929 on a weapons charge and served nine months in jail. It was the beginning of a downward spiral.

The year before, a Treasury agent named Fred Wilson had begun an investigation into Capone’s income taxes. Under a recent Supreme Court ruling, even criminals were required to pay taxes. Capone made millions but had never reported a dollar in income or paid a dime to the government.

He was charged with tax evasion in 1931 and tried in Chicago. He attempted to bribe and threaten the jurors, but the

Scarface Capone on the courthouse steps

judge caught wind and switched juries just before proceedings began.

In the end, Capone was convicted and sentenced to 11 years in federal prison. He served seven, most of them at Alcatraz in San Francisco Bay.

By the time he was released, Capone had been reduced to a shell. Fellow inmates disrespected him, he lost his influence with the Outfit, and a case of syphilis contracted in his youth drove him insane. Scarface spent the last years of his life in Florida, prisoner to delusions that old enemies were still out to get him. He died there of a heart attack on January 25, 1947.

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