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AL CAPONE IS PERHAPS the most well-known and important figure in the history of organized crime. Also known as Big Al and Scarface, little is known about his youth, other than he grew up in a rough neighborhood and was a member of two youth gangs, the Brooklyn Rippers and the Forty Thieves Juniors. He became part of the notorious Five Points gang in Manhattan, New York City, and worked in gangster Frankie Yale's Brooklyn speakeasy, the Harvard Inn, as a bouncer and bartender. While working at the inn, Capone received his infamous facial scars and the resulting nickname Scarface when he insulted a patron and was attacked by her brother.

Although Capone ordered dozens of murders and even killed with his own hands, he often treated people fairly and generously. He was equally known for his violent temper and for his strong sense of loyalty and honor. He was the first to open soup kitchens after the 1929 stock market crash and he ordered merchants to give clothes, coal, and food to the needy at his expense. These actions gave his reputation a temporary boost, until the St. Valentine's Day Massacre, Capone's most notorious crime committed February 14, 1929, in which six gangsters and a medical doctor were shot to death.

The news media distributed the death-scene photographs across the nation and the event came to epitomize the lawlessness of the Prohibition era. The massacre occurred at the headquarters of bootlegger “Bugs” Moran's North Side gang, a Capone rival. Because two of Capone's men were dressed as police, the seven victims thought it was a police raid and accordingly, they dropped their guns, putting their hands against the wall.

Using two shotguns and two machine guns, Capone's men fired more than 150 bullets into the victims. In 1930, at the peak of his power, Capone topped Chicago's new list of the 28 worst criminals and became the city's famous Public Enemy Number One.

The popular belief in the 1920s and 1930s was that illegal gambling earnings were not taxable income. However, the 1927 Sullivan ruling claimed that illegal profits were, in fact, taxable. Capone never filed an income-tax return, owned nothing in his own name, and never made a declaration of assets or income. He did all his business through front men so that he was anonymous when it came to income. Financial investigations disclosed a cash-receipts ledger that not only showed the operation's net profits for a gambling house, but also contained Capone's name; it was a record of Capone's income.

Later, Capone's tax lawyer Lawrence Mattingly admitted in a letter to the government that Capone had an income. The ledger, Mattingly's letter, and the coercion of witnesses were the main evidence used to convict Capone. In October 1931, he was convicted of income-tax evasion and was sentenced to 11 years in prison. While in Alcatraz prison, it was discovered that Capone was suffering from an advanced case of syphilis. He spent the last six years of his life as a recluse in his Florida home. In 1947, Capone died from the aftermath and complications of a stroke.

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