With Boston to the north and New York City to the south, Connecticut’s history of organized crime is often overlooked. This is the untold story of New Haven’s illegal past.

One of America’s most historic and enduring cities, New Haven has wrangled with a perpetual identity struggle, torn between worlds that occasionally converged in chaos and violence. In the 1930s, Connecticut became a region where Mafia families like the Genoveses, Gambinos, Colombos, and Patriarcas shared turf—working together with enough profits to go around or descending into open war to rival that experienced in any major city. Central to this conflict were three men who were, at different times, cautious allies or sworn nemeses. Representing the Genoveses, Midge Renault reigned supreme thanks to his reputation for wanton violence. Meanwhile, Colombo capo Ralph “Whitey” Tropiano maintained a lower profile, which belied his reputation as a vicious killer. But it was his lieutenant, Billy “The Wild Guy” Grasso, who ultimately rose to the top after joining the New England Patriarca Family, enjoying a short rule that ended with a murder plot that left him on the wrong end of a bullet.