Milazzo had been recognized as one of the Detroit Mafia's top bosses since the early 1920s and relative stability had reigned within the local underworld throughout this time, but by 1930 continuing Mafia rivalries based in New York and Chicago concerning his Castellammarese allies directly involved Milazzo. At the heart of the volatile situation within New York City's Mafia lay Milazzo's fellow Castellamarese mafiosi who found themselves being opposed by powerful boss Giuseppe "Joe the Boss" Masseria. The ongoing feud had reached a boiling point and supporters on both sides in New York, as well as Chicago were preparing for war.