Al Capone: Chicago's Most Famous Gangster
Alphonse Gabriel Capone is the most famous organized crime figure in American history. He did not build the Chicago Outfit from nothing — Johnny Torrio, who recruited him from Brooklyn, had already established the foundation — but he turned it into a multi-million dollar operation at the peak of Prohibition and became, briefly, the most powerful criminal in the United States. He was also the most visible, which proved to be his undoing. His story is the story of how American gangster mythology was created.
The Origin: Brooklyn and the Five Points Gang
Capone was born in 1899 in Brooklyn, New York, the son of Italian immigrants from the province of Salerno. He dropped out of school at 14 and fell in with the Five Points Gang under the leadership of Frankie Yale, where he worked as a bartender and bouncer. The scars on his left cheek — which gave him the nickname "Scarface," which he hated — were acquired in a fight at the Harvard Inn in Brooklyn when he insulted a young woman and her brother slashed him across the face.
Johnny Torrio recruited Capone to Chicago in 1919 to help manage the expanding bootlegging operation that Prohibition had made possible. Capone was 20 years old when he arrived in Chicago. By the time he was 26, he was running the organization.
The Chicago Outfit at Its Peak
The Chicago Outfit under Capone's control in the late 1920s was generating an estimated $60-100 million annually — the equivalent of over a billion dollars in contemporary purchasing power. The operation was diversified: bootlegging was the primary revenue source, but gambling, prostitution, and labor union extortion contributed substantially. Capone controlled the South Side of Chicago and several surrounding municipalities through a combination of bribery and violence.
His public profile was unlike any previous organized crime figure's. Capone attended boxing matches, baseball games, and charity events. He gave interviews. He distributed food to unemployed workers during the Depression. He cultivated a reputation as a Robin Hood figure that was built on genuine charitable activity layered over a criminal enterprise that used violence routinely.
The St. Valentine's Day Massacre: February 14, 1929
Seven members of the North Side Gang — the organization controlled by Bugs Moran, Capone's primary Chicago rival — were killed in a Lincoln Park garage on the morning of February 14, 1929. The killers were dressed as police officers, which led the surviving witnesses to report a police raid. The massacre eliminated most of the North Side Gang's leadership and effectively ended the competitive threat Moran posed to Capone's dominance of Chicago.
Capone was in Florida at the time of the massacre — a deliberate alibi. The killers were never convicted. The massacre was the peak of Capone's power and the beginning of its end: the public outcry, the federal attention, and the sustained FBI and IRS investigation it triggered led directly to his prosecution.
The Tax Conviction
The FBI under J. Edgar Hoover failed to build a federal case against Capone on racketeering charges — the witnesses wouldn't cooperate and the evidence was circumstantial. The IRS, working the case simultaneously, identified a different route: Capone had never filed federal income tax returns, and his cash income was provably enormous from seized records and financial analysis.
Capone was convicted on five counts of federal income tax evasion in October 1931 and sentenced to eleven years in federal prison. He served time at Atlanta Federal Penitentiary and at Alcatraz (from 1934 to 1939), where his syphilitic dementia became pronounced. He was released in 1939, significantly mentally diminished, and died at his Palm Island estate in Miami in January 1947. He was 48 years old.
Frequently Asked Questions
How was Al Capone convicted?
Al Capone was convicted on five counts of federal income tax evasion in 1931. Despite years of investigation into his racketeering activities, the federal government could not build a racketeering case that would hold — witnesses wouldn't cooperate and evidence was circumstantial. The IRS's tax evasion approach proved more successful.
What happened to Al Capone?
Al Capone was released from prison in 1939 after serving approximately eight years of his eleven-year sentence. By that point, syphilitic dementia had significantly diminished his mental capacity. He retired to his Palm Island estate in Miami and died of cardiac arrest in January 1947 at age 48.