If you think about it you would want to be someone who had great fae, and was filthy rich, and wasn't murdered, outcast, or died painfully. Preferably, never shot.

That eliminates Anastasia, Siegel, Capone, Valachi, Costello, Maranzano, Masseria, etc.

Hmm, the one who lived the longest, was the richest, and wasn't discoverd until nearly 50 years into his career, never did jailtime, the "Mystery Benefactor", Meyer Lansky.

MAYBE Lucky Luciano, but if you're not lucky i wouldnt be a Luciano or else you'dve died in 1931.