On January 17, 1899, Italian immigrants Gabriele and Teresa Capone welcomed a baby boy in their newly adopted home city of New York. They named him Alphonse Gabriel Capone but to his friends–and later the world–he was simply known as Al.

Even from an early age, Al was trouble. Although he showed promise as a student, he had trouble with the rules at his strict parochial Catholic school. It came to head when, at age 14, he was expelled for hitting a female teacher in the face. Afterwards, he worked at odd jobs around Brooklyn, including a candy store and a bowling alley; he even scored a short stint as a professional baseball player. But everything changed when he met gangster Johnny Torrio, whose nickname was ‘The Fox,’ due to the man’s cunning and finesse.

Al had scored at job at a pub run by Paul Kelly, founder of the Five Points Gang, one of the most dominant gangs in New York at the time. It was here at the met Torrio, who had an impressive mind for running legitimate businesses supplemented by incomes from bookmaking, loan sharking, hijacking, prostitution, and opium trafficking. Al quickly came to view Torrio as his mentor, and Torrio eventually hired him to bartend at the Harvard Inn, a bar in the Coney Island section of Brooklyn owned by Torrio’s business associate, Frankie Yale, who also began to mentor the impressionable young man. It was during this time that, according to legend, Al inadvertently insulted a woman while working the door, and he was slashed with a knife three times on the left side of his face by her brother, Frank Galluccio; the wounds led to the nickname “Scarface.”

Al allegedly hated the moniker.

In 1919, Capone left New York City for Chicago at the invitation of Torrio, who was imported by crime boss James “Big Jim” Colosimo as an enforcer. Within a few years, Torrio was the head of an essentially Italian organized crime group that was the biggest in Chicago, with Capone as his right-hand man. In January 1925, while walking home from a shopping trip, Torrio was shot several times. After recovering, he effectively resigned and handed control to Al, aged 26, who became the new boss of an organization that took in illegal breweries and a transportation network that reached to Canada, with political and law-enforcement protection. Under his direction, the organization grew more violent; any establishment that refused to purchase liquor from Capone’s gang often got blown up, and as many as 100 people were killed in such bombings during the 1920s. He was also quick to snuff out any perceived rivals, the most famous of these attacks being the St. Valentine’s Day Massacre in 1929, during which four of Al’s gunman disguised themselves as police officers to initiate a “police raid”. The faux police lined the seven victims along a wall and signaled for accomplices armed with machine guns and shotguns. Photos of the slain victims shocked the public, and quickly moved Al up on law enforcement’s radar.

By 1930, Al was at the top of the F.B.I.’s “Most Wanted,” but he avoided long stints in jail until 1931 by bribing city officials, intimidating witnesses and maintaining various hideouts. There was one thing he couldn’t shake however:

Taxes.

Ninety-four years ago today, on October 8, 1931, Al Capone was convicted of tax evasion, an error of his own making. Back in 1930, Ralph, his brother and a gangster in his own right, was tried for tax evasion and spent the next 18 months in prison after being convicted. Seeking to avoid the same fate, Al ordered his lawyer to regularize his tax position, and although it was not done, his lawyer made crucial admissions when stating the income that Capone was willing to pay tax on for various years, admitting income of $100,000 for 1928 and 1929, for instance. Hence, without any investigation, the government had been given a letter from a lawyer acting for Capone conceding his large taxable income for certain years he had paid no tax on.

It was an open and shut case.

Al was sentenced to eleven years in prison and fined $50,000. He spent the first two years of his incarceration in a federal prison in Atlanta. After he was caught bribing guards, however, he was sent to the notorious island prison Alcatraz in 1934. Isolated there from the outside world, he could no longer wield his still considerable influence. Moreover, he began suffering from poor health. Capone had contracted syphilis as a young man, and he now suffered from neurosyphilis, causing dementia. After serving six-and-a-half years, Capone was released in 1939 to a mental hospital in Baltimore, where he remained for three years. His health rapidly declining, Capone lived out his last days in Miami with his wife.

He died of cardiac arrest on January 25, 1947.