All time no doubt it's Tony Accardo. He started with the Capone Gang in the 1920's and ran the Outfit after Ricca went to prison in 1943 and still had an administration role in the Outfit until the 1980's. He was a top Outfit guy for over 40 years and never spent a night behind bars while guys like Ricca, Giancana, and Aiuppa were locked up.

The Genovese also had plenty of top guys who had long runs. Jimmy Alo, Jerry Catena, and Benny Squint all flew under the radar as top guys in the family.