One of the most successful wiseguys in history was Joe Arcuri. He not only successfully retired, but he was a successful wiseguy throughout his entire career. Didn't spend one day in jail, always had money and died peacefully at the ripe old age of 93. Very few people mention him.

Another guy worth mentioning is Benny Squint Lombardo. Spent relatively no time in prison, retired successfully and died old and rich.