Cavallaro was an Italian immigrant who claimed to have entered the US as a stowaway in 1921. He claimed to be a salesman of grapes used to make wine. Cavallaro became a Youngstown mob leader and was heavily involved in illegal gambling activities including high stakes dice games, the numbers racket and reportedly shared in the areas cigarette vending machine business. Cavallaro was associated with the Cleveland crime family through "Tony Dope" Anthony Delsanter and was a onetime driver and bodyguard to Detroit Partnership mobster John Mirabella. "Cadillac Charlie" was among the more successful gambling bosses in Youngstown during his time.