The Chin was probably the best to ever do it. He starts out as an amateur boxer being managed by Tommy Ryan. Then serves as a driver / bodyguard for Genovese. While working for Vito I assume he was mentored in the dope game. The boss takes a liking to him and he gets the Costello contract. Fast forward two years and he is jailed alongside his boss for Conspiracy to distribute heroin. After completing his sentence he assumes the role of captain of the Greenwich Village crew. Which so happens to have been the biggest and most profitable in the Family. Throughout the late 60's and 70's we can only speculate what business investments he had on the streets. Or what his take was from these ventures. By 81' he is officially declared the Boss. Aside from the embarrassment of Pete Savino he held a tight reign!