I think another top guy who "technically" died while free from jail, but had served many decades in prison over the course of his lifetime, was the infamous Lucchese Family capo and rapacious heroin trafficker, Joseph "Joe Beck" DiPalermo.
On that note, I believe that Joe's brother, Charlie DiPalermo, aka; Charlie Brody, falls into the same category. He did a ton of time behind jail...but technically, died while a free man.
