Not really asking who were the most cunning as those candidates are pretty much already known in Carlo, torrio, luciano, gigante ext. I'd like to know who were the mobsters that were more than just savvy street smart politician gangsters.

most you never heard of. rizzotti, stalupi..

Thank you for the response, as you hit the nail on the head I indeed have not heard of either of these individuals. Could you please give full names so I can research them more in depth?

both john's.. car biz..boat biz..

Speaking of the car business, Nicky Buick from Gun Hill is no dummy. He may not have the same money as the Colombo classic car guy. But he's still worth more than 90 percent of the guys in that family. He needed that button like his buddy Joey (the rat in Stamford) needed a hair brush.

Ponte comes right to mind. His brother was no dummy, either. He was known as the tougher of the two (and he was). But he was pretty sharp himself. Sharp enough give his smarter and better-known brother the idea to buy up half of Tribeca while it was still full of empty warehouses and ten dollar hookers.

Carlo gambino comes to mind because of his longevity, but in my humble opinion, the smartest gangsters are some people we barely hear about. Some soldiers who made their fortunes and avoided promotions and heat. If I could be a button man who just runs some gambling and whatever else, but stays out of top positions and internal battles for control, I would opt for that approach. People who can balance their greed and ambition and make it out of the life without a Wikipedia page are the smartest ones out there

Owney Madden aka the Killer.

Llewelyn Morris Humphreys aka the Hump.

William Charles aka Bill Hill.

Martin Cahill aka The General.

Appreciate all of the thoughtful responses. As a long time reader of the boards and occasional poster I'm well aware of all the big name mobsters but who can say how smart they really are/were. The unknowns are who interest me. Now to a well known figure, Michael francezze, how smart? He did go to college and did run a very sophisticated racket

Hyman "Hy" Larner aka Thomas “Red” Waterfall

This guy controlled a massive coin machine operations in Chicago, around the U.S. and other foreign contries and also headed the Independent Amusement Association under different names.He had political connections around the world, like government officals in Mexico,Ferdinand Marcos from the Philippines, Manuel Noriega and General Omar Torrijos from Panama. Through his smuggling contacts and routes for the coin machines,he also smuggled weapons and narcotics. He was also involved in the oil business and the music business. He also handled some of the cash transactions for the mob in Chicago and for some of the high profile NY mobsters.During the early 90's he faked his death by corrupting Panamanian newspapers to publish his alleged death because he had suspicion that the U.S. government was looking for him.So when the agents discovered that he was still alive they wanted again to make a move on Larner but just when it appeared the move against him was under way,the State Department had intervened and quashed the FBI’s investigation.He lived untill the age of 87 and was convicted only once in his whole life which was a very small conviction.

Frank Costello was the politically smartest Don. I believe he was the model for Vito Corleone.

For me is Tommy Gambino,the Don Carlo son was a capo thatmade a lot of $$$ controlling lucrative trucking rackets in the New York City Garment District born in 1929 made only 5 years out in the 2000 now is retired.

1 > Lucky smarts and cash

2 >Al Capone foresight to do what he did in those times, power and cash

3 >Frank Costello to be able to have the legit world in his hands at that level and cash

4 >Carlo Gambino Some of the best moves made in that life and cash ( and died at home ) Huge"

5 >Enoch Johnson had it all but big man little city or he would have been more higher on the list.

>> so Lucky for me ....

has to be frank Costello, he was a great earner, and had gambling interests all over the world.

no one had the political connections he had.

This guy vinny ferrera retired boston capo graduated boston college. Could you imagine the book he ran there and i wonder if he was in on the point skim by henry hills boys.

It sounds like the questions is which mobster had the highest IQ? Obviously that's anyone's guess, but some who had very good mathematical skills were Lansky, Dalitz, Siegel, Donald Angelina, Jimmy Napoli, and I'm sure there were plenty of others. Michael Franzese started medical school or was on his way to going to one before getting into his lucrative scams followed by becoming a movie producer, then an author and public speaker. The Desimones of Los Angeles included Frank, who was a criminal attorney before he became a Mafia boss, and his brother who was a surgeon.

In Giancanna's brother's book he said his brother told him Costello was the smartest guy he ever knew !!

Without a doubt. I've discussed Costello with you and on the board ad nauseam for years. It's just that I was under the impression that the originator of this thread was asking about mobsters who were a bit more "under the radar."

Frank Costello looks like kevin spacey

Hard to argue with the premise that the "smart" ones are the ones you don't hear about.

Americans love conspiracies. First there were the Freemasons (even though some of our Founding Fathers were members). Then the Communist Party USA. Then the Kennedy assassination. Now it's Mafia. Cosa Nostra enjoys the dubious distinction of being a "secret society" that isn't secret. Their brand recognition is right up there with Ronald McDonald and Apple. Any day now we're going to see Skinny Joey Merlino opening a vanity website and selling his own brand of hot sauce.

Joe massino. This guy always had the last laugh. Maybe just cunning but he obviously was smart. He also knew not to trust donnie brasco

Spot-on, TB. The rats are all over social media, and there are active Mafia members who have family doing reality television shows. About the Mafia.

And I can totally see the Merlino hot sauce thing.

Joey's Philly Sauce: Mild

Joey's Prison Sauce: Hot

Joey's Boca Sauce: Very hot. And humid, too.

Politically scary. Every Politician was on the take back in those days, corruption was much more widespread. The mafia changed dramatically since Costello's heyday, laws have changed, organized crime has been viewed as a serious threat by the Feds, the media got stronger each decade and public awareness of the mafia went up ten fold. How would any of us really know who the smartest was? We didn't know any of those old timers, only the "small" sample size of literature out there. It's like trying to compare Joe Montana v Tom Brady(pre-Deflategate). It's impossible to truly compare, rules have changed, offenses have changed and defenses can't even touch a guy in today's game...hence padding the stats for today's QB's.

Costello didn't have to deal with RICO, TMZ, Investigative journalists and surveillance technology that is light years ahead of where it was during Costello's reign. And the government has rooted out "in record numbers" public/political corruption through tools like RICO and WITSEC. In Costello's day, protective custody was a joke, thus not giving informants much of an incentive to cooperate.

Meyer Lansky, Joe Profaci and Tony Accardo weren't slouches either, Profaci made a fortune in Olive Oil.

Excellent points by Oscar.....very different world today....but all things being equal, Myer Lansky gets my vote....no one before or since had the business acumen that he possessed nor the corruption capabilities for that matter.

L L, funny ,,, and possible.

the hot sauce thing isn't too far fetched. merlino is opening up a chain of sub sandwich spots called "godfather subs". I shit you not.

paul ricca was the first to use a frontboss so he should be in the running

I believe it. Paramount will give him Hell over the name, though. They've successfully sued or settled out of court with just about everyone who ever tried to use the name and/or likeness of "The Godfather."

I am hearing John Alite may be opening a chain of drive in movie theaters. Dont know how many there would be. Going to be a typical drive in movie theater but with a bodybuilding/ gangster theme along with a 5 star restaurant and dry cleaning and day care services. Each would be about 15 acres.
Like the guy or not. He thinks big, assuming its true.

the guys name you don't know. the end.

Wasn't Ballistrieri a Law School dropout?