1. Moe Dalitz
2. Meyer Lansky

These two also had casinos and gambling boats in other countries. They made a lot of people money which allowed them to die of old age and not in the gutter. There are many and I can think of another two dozen guys who would be up there, but in terms of accomplishments and money plus their failures they don't come close except for Milton Rockman, Frank Costello, Anthony Accardo and Tony Salerno but still below those two guys.