I agree with a lot of the people who say Accardo and Gambino. I'm kind of torn between which one takes the cake though. On the one hand, Accardo ruled for a much longer period of time. On the other hand, the New York families (at least the big three) were on a whole other level of organization and discipline compared to the Outfit. Being the boss of one of the New York families somehow seems like a greater accomplishment.

Another guy that I would consider to be in the top 5 is Stefano Magaddino. He was a big shot in New York in the early 1920s, and then ran things in Buffalo for something like 45 years. I don't think any boss except Accardo has controlled his turf for so long.