 At age 16, Battaglia joined bosses Johnny Torrio and Al Capone in the Chicago Outfit at the start of the gang war against the mostly Irish North Side Gang, which was under boss Dean O'Banion.By the late 1930s, Battaglia had become a high-ranking member of the Outfit and a formidable loan shark.Debtors behind in their payments would be brought to Battaglia in the back room of the Casa Madrid restaurant, in Chicago, where they would be severely beaten or killed.