Frank "The Enforcer" Nitti

Francesco Raffaele Nitto, better known as Frank "The Enforcer" Nitti (January 27, 1888 — March 19, 1943) was an Italian-American gangster, one of the top henchmen of Al Capone and later a mob boss in his own right.

Nitti was born in Sicily in the 1880s; his gravestone lists his birth year as 1888, but his US immigration documents say 1883. He emigrated to New York City after the end of the First World War, and later moved to Chicago, Illinois, where he set up business as a barber, with a profitable line as a jewel fence on the side. He built an extensive network of associates in the Chicago underworld, and came to the attention of Chicago Mafia boss Johnny Torrio. Later, for Torrio's successor Al Capone, Nitti ran Capone's Prohibition busting liquor smuggling and distribution operation, importing whiskey from Canada and selling it through a network of speakeasies around the city. Nitti was one of Capone's top lieutenants, trusted for his leadership skills and business acumen; despite his nickname "The Enforcer", Nitti used Mafia "soldiers" and other underlings rather than undertake much of the violence himself.

In 1930 Nitti, like Capone, was charged with income tax evasion. Capone was sentenced to eleven years, Nitti to 18 months. Upon his release, he was hailed by the media as the new boss of the Chicago Mafia; in practice he lacked the control over the capos that Capone had enjoyed, and the Capone empire began to fragment, with Nitti acting as a frontman. On December 19, 1932 two Chicago police officers shot Nitti in his office, nearly killing him. Some historians believe they were acting under orders from Mayor Anton Cermak (who, they believe, wanted to redistribute Nitti's empire to gangsters favorable to him). One of the police officers shot himself (non-fatally) to make the shooting look like self-defense.

Unfortunately for the Chicago police (and whoever was behind the shooting), Nitti survived and was acquitted of attempted murder in a February of 1933 trial. The two Chicago police officers responsible for the Nitti shooting were then summarily dismissed from the police force. Cermak decided to take an extended vacation and hang out with President-elect Franklin Delano Roosevelt in Florida. On the night of Feb. 15, 1933, a former Italian army marksman, Giuseppe Zangara, was waiting in a crowd at Bayfront Park in Miami. Zangara had three things going for him as an Outfit assassin. He had an inoperable disease, he had a family and he had a gun. From about 30 feet, he popped Cermak in the chest. Roosevelt was not injured because he wasn't the target. Zangara was later executed.

In 1943, many in Chicago organization were indicted for extorting a number of the largest Hollywood movie studios. Many of the higher-ups in the mob, most notably Nitti's second in command Paul Ricca, believed Nitti should take the fall for the rest of them. Fearing another long prison term and possibly suffering from terminal cancer, Nitti shot himself dead in Chicago's Illinois Central railyard on March 19, 1943.