Born in Chicago, Illinois, Daddano became a member of the Forty-Two Gang, a local street gang from Maxwell Street on Chicago's West Side. Gang members included future Outfit heavyweights as Sam Giancana and Sam Battaglia. Daddano also had the responsibility to know who every Chicago burglar was, so that the Chicago Outfit could take a "street tax" percentage of everything he stole. A legitimate business that Daddano owned and operated in much of Chicago was a garbage collection company named, "West Suburban Scavanger Service."