I'd say Carlo gambino was. I mean he ran the crime family for 20 years and avoided any significant jailtime. He also was the boss of bosses at a time when the mafia was in full force. He was probably one of the smartest dons ever. Also Santo Trafficante was another guy who ran his thing in Florida without drawing much attention
As good as Gambino, Accardo and Trafficante were I think the obvious answer Is John Stanfa. Time after time Stanfa showed his brilliance and acuity. He was clearly in a league of his own when it came to out foxing his enemies and law enforcement. I kid I kid.
Seriously though, I agree with Gambino and Trafficante but believe Tony Accardo deserves mention too. He lead the Outfit for decades and never spent a day in jail.
I'm not sure exactly what year Accardo became the official boss but I believe it was some time in the mid to late forties and he had the final say on all Outfit business until his death in 1992. Even when Accardo took himself down and made himself the "consigliere" giving the title of boss to Giancanna and later to Joey "Doves" Aiuppa, I think everyone would agree that Accardo was the one with the most power and influence and had the final say.
