Name all the bosses throughout the country who were lucky enough to die in the comfort of their own beds, “with their shoes off” as the saying goes. Not in a cold prison cell, or worse, shot to death or slaughtered in the streets like dogs.

I’ll go first with a few….

Francesco “Frank Costello” Castiglia
Joseph “Joe Bananas” Bonanno Sr.
Gaetano “Tommy Brown” Lucchese
Carlo “Don Carlo” Gambino
Giuseppe “Joe” Profaci
Simone “Sam the Plumber” DeCavalcante

Santo Trafficante. I think the only one that got him to do prison time was Castro.

Stefano Magaddino?

I really believe that Vito Genovese was set up or framed. If not for that, who knows? The late early 1980s early 90s bosses seemed like they weren't even trying to stay out of prison, after watching what happened to the bosses of the Commission Trial, who were more shrewd than them. Chin Gigante and Joe Massino were the only ones from that era who had any sort of longevity.

Didn't Carlos Marcello die free? What about Jack Dragna?

Some bosses or alleged bosses who I won't name seem to have been on the streets for quite a while now, especially for this day and age.

Vito Rizzuto made out like a bandit after his involvement in the 3 Captains Murder was confirmed and died free. Does he count, being from Canada?

Liggio,
I don't see why not.
How about the original, Salvatore Lucania?
I see a trend here.

Frank Tieri almost made it lol. He probably saw prison as a nursing home.

Peter Milano - L.A.
Anthony Civella - KC
Carlos Marcello - N.O.
Emmanuel J. Figlia - San Josè
Frank Balistrieri -Milwaukee
Vito Rizzuto - Quebec Mafia
Joseph Massino - Bonanno (flipped)
Joseph Todaro Sr. (Buffalo)
Joseph Magliocco (Colombo)
Frank Valenti (Rochester)
Giovanni Riggi (DeCavalcantes)
Antonio Pollina (Philadelphia)
Peter Limone (Patriarcas)

James Lanza, the longtime boss over the City of San Francisco.

Joe Cerrito, the boss of San Jose, CA.

Here's a few more...

Buffalo Acting Boss, Salvatore "Sam the Farmer" Frangiamore

Buffalo Underboss Frederico "Lupo the Wolf" Randaccio

and future Buffalo boss Joseph "Lead Pipe Joe" Todaro Sr.

Frank "Frankie Bal" Balistrieri, boss of Milwaukee

John Scalish (Cleveland)

The 100% correct, mobcleve…

And for that matter, let’s not forget two more former Cleveland bosses who retired with lots of money, living out the rest of their days in peace and financial splendor, Francesco “Ciccio” Milano and Alfred “Big Al” Polizzi

At one time, Cleveland had a lot of solid guys.

Another west coast guy...

Los Angeles, California boss, Nicola “Nick” Licata

Anthony Accardo!

No doubt about it. Tony Accardo lived one hellva life, an envied life...especially for a top boss.

For that matter, although he did serve some prison time, Felice "Paul Ricca" DeLucia definitely falls into this category also.

Dominic Longo, aka Toyota Dom, of the Dragna Family, died free and wealthy. I give credit to Scott D of the Gangster Report.

He wasn’t a boss though, but in some cases it's better to not be.

Agreed, he was only soldier.

But sometimes, as you already stated, it's much better to be a soldier. In this case, a free and wealthy soldier rather than an incarcerated boss.

New England’s boss, Filippo “Phil” Bruccola. If I remember correctly, he even retired back to Italy to enjoy his last years.

For that matter, another top boss who did the exact same thing was early Philadelphia leader, Giuseppe "Joe" Ida.

Old-time Canadian N'drangheta boss (and Buffalo/Maggadino member) Giacomo "Don" Luppino.

Philip 'Rusy' Rastelli died in his own bed. Boss of the Bonanno's for nearly 20 years.

He didn't die in prison.

I believe you're right. But I know when Rusty got out he was already cooked...very sick.

Another top Outfit guy that I just remembered who also deserves to be on this list was their North Side skipper, Ross Prio. Athough not nearly as well known or ranked as high as an Accardo or Ricca. Nonetheless, Ross Prio was long considered a top leader in Chicago’s underworld.

Ross was another guy who lived a good life and died in his own bed with his shoes off.

Longtime Genovese Family consigliere and Vito's personal confidante, Michele “Mike” Miranda

The Genovese Family’s longtime resident overlord for the State of Massachusetts — Capodecina, Salvatore “Big Nose Sam” Cufari

Longtime Pittsburgh, Pennsylvania Family boss Sebastian “John” La Rocca

Rockford, Illinois, Frank Zito Family “consigliere” Giuseppe (Diamond Joe) Zito