Vincent Drucci (born Ludovico D'Ambrosio; January 1, 1898 – April 4, 1927), also known as "The Schemer", was an American mobster during Chicago's Prohibition era who was a member of the North Side Gang, Al Capone's best known rivals.

[citation needed] After serving in the U.S. Navy, he returned to Chicago and started committing small-time crimes such as breaking open pay telephone coin boxes.

He joined Dean O'Banion's North Side Gang, which had taken over the formerly legal breweries and distilleries in that part of the city giving them massive profits from illicit production of alcohol, in addition to shakedowns and other rackets.

Often described as mainly Irish-American, after O'Banion's death the North Side Gang was successively headed by Hymie Weiss, Drucci and Bugs Moran who were respectively of Polish, Italian and French descent, while the most influential members who never became leader were Louis Alterie, of Spanish parentage, Samuel Morton who was from a Jewish background, and the German Albert Kachellek.

Though a leading member of the relatively small gang, Drucci acted as enforcer and was actively involved in numerous violent incidents; on one occasion when ambushed in the street by gunmen with a Capone trademark driveby, he charged at the assailants and tried to give chase in a hijacked car.

Laurence Bergreen, in his book, Capone: The Man and the Era, describes Drucci: He had a streak of recklessness and daring, and he looked the part of a gangster – tough, dark, and menacing, his expression frozen in a tragic mask topped by wild unkempt hair (and) a face to haunt the dreams of his enemies.He was known by the nickname "The Schemer", in part because of his penchant for inebriated rumination about outlandish plans; in reality he operated by intimidation in activities such as extortion of money from legitimate businesses.

Drucci, whose practical jokes including making salacious comments to couples on the street while dressed as a priest, performed in a 1923 pornographic film called Bob's Hot Story.

[1] The North Siders found themselves undercut on the price of alcohol by rivals the Genna crime family, which was allied to the Italian American South side gang led by Johnny Torrio, who had pretensions of citywide overlordship.

On January 25, 1925, Drucci, Weiss, and Moran ambushed Torrio's bodyguard-lieutenant, Al Capone, shooting up his car, but failing to kill him; his bodyguard was then kidnapped, tortured and murdered.

The North Side Gang responded with an even more high-profile assassination attempt, using a ploy to lure Capone to the front of the Cicero, Illinois hotel in which he lived, and then firing hundreds of rounds through the windows.

In 1927 William Hale Thompson at the head of his powerful Cook County machine that included strong support among African American districts, attempted to return as mayor.

Exploits such as a near-fatal beating of Capone rival, Joseph Saltis, during a November 1926 saloon raid, had gained Healy a reputation for apoplectic violence against criminals, though not always in the line of duty.

A remnant of the North Side persisted alongside the similarly weak Roger Touhy, but got eliminated during Capone's push back against the allies of Cermak.