Tony Genna

Antonio "the Gentleman" Genna (; July 12, 1890 – July 8, 1925) was an Italian-born mobster in Chicago. He headed the Genna crime family with his brothers. Genna was ambushed by a Genna family turncoat on orders of North Side Gang leaders Vince Drucci and Bugs Moran.

Early life Antonio Genna was born on July 12, 1890, to Sicilian parents, Antonio Genna Sr. and Maria Concetta Utica in Marsala, Sicily. He had six brothers: Michele, Vincenzo, Pietro, Salvatore, Angelo, and Nicola Genna; and two sisters: Rosa Laudicina and Caterina Mariana. He and his brothers entered the U.S. through New York around 1910.

Legitimate business Before becoming a gangster, Genna was a building contractor and architect. Francesco Ioele and two Genna hitmen—Giovanni Scalise and Alberto Anselmi—entered O'Banion's flower shop, Schofield, and when Yale shook O'Banion's hand, Scalise and Anselmi shot two bullets into his chest and two in his neck. While O'Banion was lying face-down on the floor, one of the men shot a final bullet in the back of his head.

Personal life Genna had a girlfriend named Gladys Bagwill, whom the rest of the Gennas did not like due to her not being Italian. She was a minister's daughter. Apparently, Genna had planned to marry her (before he was killed). The Aiellos had an alliance with Castellammarese Clan boss Salvatore Maranzano and a close connection to the North Siders. They attempted to murder Capone to become the most powerful Italian organization in Chicago. In 1930, Joe Aiello was murdered and Capone took over the territory.