Besides being a racketeer and notorious criminal, Drucci was a first-class goofball. He earned his nickname, "Schemer", for the wild, harebrained ideas he was constantly dreaming up for stealing the crown jewels, bringing down the U.S. government, running for Mayor, or some other equally ridiculous plan. As a practical joker, he was unparalleled among gangsters, and was famous for walking around dressed as a priest, while making mischief among those he happened to come across.
He rose through the O'Banion organization, becoming second in command under "Hymie" Weiss after O'Banion's death, and taking over the leadership when Weiss was assassinated. A ruthless killer, he held the distinction of murdering two consecutive presidents of the Unione Siciliana, Angelo Genna and Sam Smoots Amatuna.
He made countless attacks on the lives of Al Capone and other members of the Torrio-Capone syndicate. During 1926, while Capone was sequestered away from Chicago in Lansing, Michigan, waiting for the heat from the Bill McSwiggin murder to pass off. The Northsiders took this opportunity to expand the reach of their gang. When Capone returned to the city, he decided to send a message to Drucci and company. One of Capone's loyal deputies, Louis Barko, engaged Hymie Weiss and Drucci in a firefight through the streets of the Loop, leading to Drucci's arrest. It was this event that triggered the Northsiders' revenge attack upon Capone's Cicero headquarters, the Hawthorne Inn.
Schemer Drucci's run of luck ended in a rather inglorious way. April 4, 1927 was mayoral election day in Chicago. "Big" Bill Thompson, the Republican candidate who had previously served as second ward alderman and whose career was guided and mentored by the corrupt vice king-aldermen of the first ward, Hinky Dink Mike Kenna and Bathouse John Coughlin, was running on a "wet" platform against "Decent" William Dever. For his anti-prohibition stance and general amenity to corruption, Thompson was gangland's choice, and Drucci decided to help his man in the best way he knew -- by kidnapping Dever's supporters. After breaking into the office of Dever's biggest supporter on the City Council, Lincoln Park Alderman Dorsey Crowe, Drucci managed to get arrested and, after some legal wrangling, ended up in a police car headed for the Criminal Courts building downtown.
His police escort included one of Chicago's toughest cops, Dan Healy. Healy's description of what took place during that car ride follows:
Drucci said, "You -- I'll get you. I'll wait on your doorstep for you." I told him to shut his mouth. Drucci said, "You take your gun off me or I'll kick hell out of you." He got up on one leg and struck me on the right side of the head with his left hand, saying "I'll take you and your tool. I'll fix you," grabbing hold of me by the right hand. I grabbed my gun with my left hand and fired four shots at him."Drucci was shot in the back of the police cruiser while stopped for traffic on the Clark Street bridge over the Chicago River, pictured above. Despite pleas from his attorney, Healy was never seriously investigated for the killing, since the police were more than happy to see Drucci gone. Even Drucci's widow found her self less than distraught over the decease of the gangland leader. Inheriting his half-million dollar estate, she is reported to have said at his funeral (organized by John Sbarbaro, of course), "We sure gave him a great send off."