Known as "The Gentleman", Tony was one of the six Genna brothers who controlled the Little Sicily section of Chicago during prohibition and fought a bloody gang war against Dean O'Banion's the North Side Gang. Tony was a shrewd building contractor and Architect. In this profession, he could have amounted to something honorable, but the lure of fast cash and power ultimately won over his mind as a way of life. Tony was an intelligent aristocratic type of fellow, and his building abilities had led to having his mark on most of the homes being built at 55th and Troy streets in Chicago.