Francesco (Frank Costello) Castiglia for me would probably be Numero Uno :
1) wealthy beyond belief.....a multimillionaire many, many, many times over!
2) very accomplished with vast far flung highly-successful businesses and industries, extensive real estate income, stocks, high finance, liquor distilleries, etc., owned the Copacabana, points in several Las Vegas casinos, Wall Street properties, Kings Ransom Scotch, etc.
3) NOT a vicious guy. In fact he shunned violence for the most part and encouraged mediation and compromise which in retrospect served his life and career well
4) VERY well liked and respected
5) served only a few years in prison related to income tax evasion, perjury, and a contempt charge (less than 5 years totally inside a jail cell collectively)
6) lived a life which was the envy of many: a multimillion-dollar apartment on Central Park West, a sprawling estate in Sands Point, Long Island worth many millions, a world traveler, he ate in the finest of Manhattan restaurants nightly and wore the finest custom made clothes, etc, etc
7) lived to the ripe old age of 83 and died with his alligator shoes off in his own bed wearing silk pajamas
8) even his rackets primarily consisted of liquor bootlegging, slot machines, bookmaking, shylocking, casino games, diamond smuggling, etc.....NOT NARCOTICS OR MURDERS, etc
9) I could go on, but I think I've made my point
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As # 2: Gaetano Lucchese also falls into this general category although not as lofty as Costello
as # 3: ...........there are several others in this category Carlo Gambino, Gerardo Catena, etc......(and actually some mostly unknown soldiers who also ranked well into this category but whose surnames were not as well known to the public).

THATS MY THREE!