Case File: Al Capone

There’s little to suggest that Alphonse Gabriel Capone, born in 1899 in Brooklyn, N.Y., would become one of the most famous gangsters in history. One of nine children born into a stable, hard-working Italian immigrant family, he appeared to be a good student until he lost his temper and struck a teacher at age 14; he never went back to school after that.

Before long, Capone was involved in the notorious Five Points Gang, a group of Irish- and Italian-American criminals in Lower Manhattan. It was there that Capone met Johnny Torrio, a racketeer who would become his mentor.

Capone also tried various “honest” jobs, including working in a munitions factory, at a bowling alley, at a candy store and as a paper cutter. By the age of 19, he was married with a son. A job as a bouncer proved unlucky when Capone made a lewd remark to a pretty woman; a man attacked Capone with a knife in response, badly slicing the left side of his face. Much to Capone’s annoyance, he was thereafter known as Scarface.

By 1919, Torrio had been living in Chicago for about 10 years, working under mob boss James “Big Jim” Colosimo, who was making a fortune in gambling, prostitution and racketeering. Torrio convinced Capone to join him in the Windy City, which was ripe with opportunities for ambitious young criminals. He was soon joined by his family, who settled into a middle-class neighborhood in Chicago’s South Side.

When the 18th Amendment ushered in Prohibition in 1920, it opened an enormous market for bootleggers, but Colosimo was reluctant to get involved. That didn’t sit well with Torrio and Capone, and shortly after Capone arrived in Chicago, Colosimo was shot and killed. Some investigators believe Capone had a hand in his murder.

Following Colosimo’s death, Torrio and Capone quickly took control of their gang, now dubbed The Outfit, and moved into the lucrative bootlegging business, importing illegal liquor from Canada. Chicago’s extensive railroad network made shipping alcohol nationwide easy and profitable.

“Johnny Torrio, perhaps more than anyone in Chicago, sees the potential and recognizes that this could be a huge business, that they could make more money than they’ve ever dreamed of. This is like Microsoft,” Get Capone author Jonathan Eig told Chicago Stories. “One of the biggest industries in America had just been declared illegal. So if you are willing to try to step in there and take it over, people still want this product. There’s demand. All you have to do is create the supply.”

The mobsters running liquor sales were ruthlessly competitive, and The Outfit was challenged by a North Side Chicago gang led by Dean O’Banion and Bugs Moran. Shootings, bombings and other violence were commonplace among rival gangs, and after Torrio set up the murder of O’Banion, the North Siders sought revenge by shooting Capone on January 12, 1925, and Torrio on January 24.

Both men survived the attacks, but Torrio was badly hurt, leading him to retire in 1925. His departure left a 26-year-old Capone as the sole leader of a vast criminal enterprise of nightclubs, brothels, gambling joints, breweries, bootleggers and speakeasies that brought in an estimated $100 million a year.

The newly minted multimillionaire quickly settled into a flashy, lavish lifestyle. In 1928, he bought a villa in Palm Island, Fla., formerly owned by Clarence Busch, scion of the Anheuser-Busch brewing dynasty. To escape political heat in Chicago, Capone’s gang set up shop outside city limits in nearby Cicero, Ill.

Like many mobsters, Capone bought some measure of community support in Cicero by spending part of his fortune on local charities such as soup kitchens. These moves earned him a following as a Robin Hood figure, getting rich by providing jobs—and alcohol—to people who needed work and resented Prohibition (which, by the late 1920s, was an increasingly unpopular regulation).

Despite Capone’s charm offensive, many citizens and local officials grew weary of the constant mob violence wracking their communities. Calls for reform reached a fevered pitch in 1929 after the infamous St. Valentine’s Day Massacre, during which seven members of Moran’s North Side gang were ruthlessly gunned down in a Chicago garage.

The gruesome news and photographs of the slaughter made headlines worldwide, and though Capone was never indicted for the massacre—he was at his Florida estate at the time—all the evidence pointed to The Outfit. By some estimates, Chicago turf wars caused about 700 deaths during the 1920s, and the public had had enough.

Soon, everyone from President Herbert Hoover to beat cops in Chicago were after Capone. He was arrested in 1929 in Philadelphia for carrying a concealed weapon, for which Capone served nine months in Pennsylvania’s Eastern State Penitentiary. Soon thereafter, the Chicago Crime Commission came out with its first list of “public enemies.” At the top of the list was Alphonse Capone, now known as Public Enemy No. 1.

Capone’s legal woes continued in April 1930 when he was arrested in Miami Beach on charges of vagrancy. He was later acquitted, but despite that his presence in South Florida was an irritant to many in the community who feared his unsavory reputation would make the region less attractive to tourists and investors.

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. Capone’s lavish lifestyle gave prosecutors all the evidence they needed to secure a conviction.

In 1931, Capone was charged with tax evasion from the years 1925 to 1929 and with 5,000 violations of the Volstead Act (which ushered in Prohibition by making liquor sales illegal). Capone pleaded guilty because he believed he had negotiated a plea bargain with prosecutors. The judge in his case, however, informed Capone that he was not bound by any plea bargains, so Capone changed his plea to not guilty.

The legal wrangling didn’t work in Capone’s favor, and in October 1931, he was found guilty of tax evasion and sentenced to 11 years in prison plus hundreds of thousands of dollars in fines and back taxes. Capone began serving his sentence in the U.S. Penitentiary in Atlanta, but after he tried bribing guards to continue running The Outfit from prison, he was transferred to Alcatraz Federal Penitentiary, the infamous island prison in San Francisco Bay.

Capone was released from Alcatraz in November 1939 after paying all his fines and back taxes, but he never again recaptured the power he had before prison. He was diagnosed with untreated syphilis, and the disease had affected his brain and nervous system so severely that he had the mentality of a 12-year-old child.

Capone spent his final years in isolation at his villa in Palm Island, Fla., surrounded by his family. He died after a stroke and cardiac arrest in 1947 at the age of 48.

The Outfit continued operating after Capone’s conviction and incarceration in a somewhat diminished capacity. The end of Prohibition in 1933 further eroded the mob’s revenue stream, though organized crime continued to exist in Chicago and other major cities.

Years after his death, Capone and his murderous, criminal underworld became emblematic of the negative effects of prohibition of liquor as well as drugs. Many observers credit Prohibition for giving rise to vast networks of organized crime.

“In his 48 years, Capone had … demonstrated the folly of Prohibition,” wrote Capone: The Man and the Era author Laurence Bergreen. “As he was at pains to point out, many of his crimes were relative; bootlegging was criminal only because a certain set of laws decreed it, and then the laws were changed.”

Capone’s life and times have been the subject of numerous books, films and television shows, including Scarface, a 1932 film starring Paul Muni, and The Untouchables, a 1987 movie starring Kevin Costner and Robert DeNiro.