A prominent member of Al Capone's organization during Prohibition, Mangano oversaw criminal operations in the Near West Side of Chicago, including illegal gambling, fencing, extortion and prostitution. Although Mangano received police protection through bribery, in 1928, a number of Mangano's establishments were raided by police Captain Luke Garrick. Garrick's house was then bombed in retaliation. Although Garrick survived the bombing, no further interference was taken by local law enforcement in the district. Over the course of his life, Mangano claimed he had been arrested over 200 times without ever spending a night in jail, explaining, "They were all bum raps...and besides I had good lawyers."