I would've thought judging by your name that Joe Masseria would be one of your choices haha.

Frank Costello - A decent and reasonable man by mob standards who had a great mind for that way of life and focused on profiting over warring. My thinking is that if he wasn't involved in that line of work then he would've prospered in the world of legitimate business.

Bugsy Siegel - May not have been the most smartest but to me he's the definition of a bad ass and boy what a life he lived. One thing that fascinates me to no end is the fact that he had met Benito Mussolini, Joseph Goebbels and Hermann Goering prior to the second world. He was connected to Mussolini through a countess he was having an affair with and wanted to sell Mussolini weapons. He apparently disliked Goering and Goebbels' Nazi ideals and the way they carried themselves so much that he was compelled to have them killed which would be a stupid idea judging by the positions those two men held.

I also want to mention Joe Masseria whom i don't necessarily like but have a lot of interest in.