Milazzo aligned himself with Salvatore Catalanotte, known as "Singing Sam", the local head of the Unione Siciliana and one of the leading and most respected Sicilian Mafia bosses in Detroit who was only in his mid 20s at the time. Milazzo and Catalanotte led two of the more powerful and influential Mafia factions within the Detroit area and together they would align the city's Mafia factions into a loosely organized and cohesive unit that controlled bootlegging, gambling, narcotics, prostitution and other rackets within the city of Detroit and surrounding areas.