I'm curious who forum members think was the most financially successful, yet low-key mafioso to ever operate in NYC. It doesn't have to be limited to just one name either, because I know there are so many to choose from. Each forum member participating can choose up to 3 mafiosi.

So with that said, here's the criteria to go by:

1. financially successful, both in money and "assets" (real estate, businesses, etc)
2. served little to no jail time (or tops 1 moderate jail term)
3. held legitimate business interests as well as racket interests. He wasn't just a hoodlum
4. Not a vicious guy. Maybe did what had to be done, but wasn't an out and out animal.
5. and finally, lived a long and happy life. Both in years on this earth as well as a wealthy and opulent lifestyle...ie; nice home, vacations, fancy clothes, girlfriends, cars, etc.

Let's see what the varied opinions are.

One more criteria. KEEP THE CHOICES TO NEW YORK CITY OR NEW JERSEY MAFIOSI ONLY...........NO OUT OF STATE GUYS!

My picks would be
Tommy Lucchese: Machiavellian mobster, relatively successful thanks to rackets in clothing, construction, etc., made strong alliance with Gambino
Carlo Gambino: obvious reasons, very wealthy thanks to mob connections, forger better relations with Lucchese.
Benny Squint Lombardo; very low key, preferred to delegate authority to high-ranking grunts like Funzi Tieri, Chin Gigante, or Fat Tony. Died a free man.

Would have chosen Tony Accardo and Paul Ricca, but they're non-NYC mafiosi.

You don’t get points for pre 80s. Carlo Gambino and tommy lucchese would have been doing life ..Law enforcement and the laws themselves are completely different today..Michael Lancelotti from philly Ralph Lombardo and Vinny Aloi from the Colombo’s ..Joe Arcuri from the gambinos...Anthony desimone From the luccheses. Barney from the Bronx and joe Dente Jr from the Genevose

Richie "The Boot" Boiardo from Newark would be my pick. He had legitimate businesses,a beautiful estate,served some jail time,(but not much), was well respected,and active into his 80"s.He was well respected,and could certainly "take care of business" if he had to,but wasn't a brutal guy. He did however flash it up a little by building a really ostentatious home,complete with gaudy statues of himself and his family. He had a sign that read "Godfather's Garden" near the gate,and rumor has it that he had an incinerator on the property to dispose of "evidence" What is really chilling is that,according to rumor, some of the "evidence" was still alive at the time.

Francesco (Frank Costello) Castiglia for me would probably be Numero Uno :
1) wealthy beyond belief.....a multimillionaire many, many, many times over!
2) very accomplished with vast far flung highly-successful businesses and industries, extensive real estate income, stocks, high finance, liquor distilleries, etc., owned the Copacabana, points in several Las Vegas casinos, Wall Street properties, Kings Ransom Scotch, etc.
3) NOT a vicious guy. In fact he shunned violence for the most part and encouraged mediation and compromise which in retrospect served his life and career well
4) VERY well liked and respected
5) served only a few years in prison related to income tax evasion, perjury, and a contempt charge (less than 5 years totally inside a jail cell collectively)
6) lived a life which was the envy of many: a multimillion-dollar apartment on Central Park West, a sprawling estate in Sands Point, Long Island worth many millions, a world traveler, he ate in the finest of Manhattan restaurants nightly and wore the finest custom made clothes, etc, etc
7) lived to the ripe old age of 83 and died with his alligator shoes off in his own bed wearing silk pajamas
8) even his rackets primarily consisted of liquor bootlegging, slot machines, bookmaking, shylocking, casino games, diamond smuggling, etc.....NOT NARCOTICS OR MURDERS, etc
9) I could go on, but I think I've made my point
______
As # 2: Gaetano Lucchese also falls into this general category although not as lofty as Costello
as # 3: ...........there are several others in this category Carlo Gambino, Gerardo Catena, etc......(and actually some mostly unknown soldiers who also ranked well into this category but whose surnames were not as well known to the public).

THATS MY THREE!

New York/New Jersey only? Figures 'cause if it didn't happen there then it just didn't happen!

LOL...I'd say that's a somewhat bitter response Henry? ...What happened? Somebody shoot your cat or something?

I qualified it to the NY/NJ area because to consider the entire country was a bit too expansive for my taste. And since I'm the one posing the question, It's my choice no?
Plus, the fact that this region is so huge with wiseguys and racketeers I figured there was more than enough subjects to choose from. (Not to mention the fact that like it or not, whether you'd like to admit it or not, the New York greater metropolitan region is, and has always been ground zero, and the epicenter of Italian OC in this country)...period! An indisputable fact!

There are a lot of top guys throughout the country, but this time around its the NY/NJ area.

Participate of not. That's entirely up to you - "Friend of Henry"!

That certainly wasn't "a somewhat bitter response". It was a somewhat factual response. It's just the way it is. The bigger the city the bigger the interest and New York has always been the city of most interest. Since I only know what I know from personal experiences instead of living vicariously through research I can't participate 'cause I have no first hand knowledge. Ok with you - "Maxie"?

Two more iconic old-timers to consider would be Michele (Mike) Miranda and Ettore (Terry) Zappi.

Both were very wealthy and served very minimal time in jail. Miranda was a potentially vicious guy, whereas Zappi was anything but. But they both pretty much met all the criteria I laid out earlier for our choices. Both lived successful lives and died natural deaths at ripe old ages in their own beds.

As I say the one marked difference being the propensity for violence issue. Having been the main sidekick to Vito Genovese, Miranda was without a doubt a very dangerous guy who did a lot of work in his day.

Whereas Zappi, although no pushover himself, was not an inherently vicious mafioso.

So much sexual tension between you two

Jimmy Brown, Gambino heavyweight who controlled the garbage industry. Very low key and was hard to pin down by the FBI. Well respected by all the families and was placed in various leadership positions throughout his later years within the Gambinos.

Low key means we never heard of them and I bet there's alot in every family. Usually the big cash cows dont rise above soldier so they dont raise suspicion. Jimmy brown was in the papers and died in jail so....

Well said Mr. "Henry", I applaud your candor. And yes I do agree with your assessment. The bigger the city, the bigger the interest. So of course The Big Apple stands alone in that regard....always!

Nonetheless, it's good that you recognize your limitations "Henry"... stay with what you know, your strengths so to speak.

Even if you feel that you can't contribute to this particular discussion, I will be posting up several stories as well as interactive "give and takes" such as this one for forum members in the near future. Hopefully you will find those more to your liking.

I do welcome whatever constructive information and contribution you may have to give.

Hope to speak with you again in the near future.... "The Other Guy!" (or if you prefer Maxie) ;-))

LOL.... ya think? ;-)))

I have to agree with you there. Jimmy Brown started out close to Carlo Gambino. So much so that JB was Carlo's personal driver-bodyguard and confidante for many years.

He was there daily with Carlo to "see and hear" nearly all that went on. As you said, he was later elevated and controlled the entire NYC carting industry for that crew for decades.

A very well respected guy. But pmac is correct too in that JB later took a big Rico pinch and went down for what, 10-15 years in the can? NOT a great ending to an otherwise low key and successful mob career.


***Another point that pmac makes that I'd have to wholeheartedly agree with is that many, if not most "low key", under the radar mafiosi who make millions and avoid jail are usually virtual "unknowns" to the public, LE, and forums such as this one. Or in the alternative, may be known but largely stay out of the limelight, especially after they reach a certain financial level of success and a "station" in the mob as a "made" guy.

They DON'T want a higher position or to be elevated to a capo post or higher. They well know that it's a death kneel. Better to make the cash and stay out of the limelight (which in turn usually keeps them out of jail as well)....... An astute observation pmac.

My compliments!

I Disagree. Obviously technology and laws changed but to say that they had it much easy when it came to law enforcement is not true. It was more about the lack of knowledge, its easy to start convincing people when you have been collecting info on the organization for 50yrs. if it was so lax, how do you explain Luciano or Genovese going to the can. And even Capone (eventhough it was bullshit tax charge but they still got who they were supposed too) and Bonanno's legal problems in the 60s.
Then you have guys like Benny Squint and Gerry Catena who missed the problems of the 80s

Again, I would have to agree with Peppino on this one.

Granted, LE was not nearly as sophisticated as they are in recent decades, but There are sharp, quiet and careful mafiosi who are able to know when to go into something (and how far and in what manner), and then there are wild men and loose cannons who just don't give a good fuck and try and "bull" their way through that life.

Those are usually the guys who die in the gutter, or die in prison never seeing the light of day. A Galante. A Genovese. etc...

Then you have your Carlo Gambino's, Tommy Lucchese's, and the like who thread slowly and are "thinkers" and are the tacticians in the underworld. They are mostly the fellas who die in their own beds free as Jay Birds. They get to die on their owns terms, surrounded with their loved ones and the millions they've made. Like Frank Costello and Sam DeCavalcante, etc.

Prior to 1980s when you were indicted by the fbi you were able to fight your case before you were jailed,now your held without bail “as a danger to the community”...when your convicted if you got 20 years back in the day you qualified for parole after 6..now you have to do 85% of your time..not to mention you could appeal your conviction and we’re free on bail prior to sentencing..not to mention the forfeiture laws..
In the early 1970s Carlo Gambino went to trial for robbery conspiracy and beat the case..prior to trial,he was out on 75k bail..today he would have been held without bail ,which means in jail not free which makes it so much harder to fight your case and he would have lost control of his crime family while jailed and turned over leadership

Believe me Carl is light years ahead of the Gavones coming up today but no matter how smart and cunning he was ,had he come along 10 years later.he would have got 100 years in the commission case... nick civella was brilliant and really understood the human animal..but once the 80s came around and the laws changed he was no match for the FBIs organized crime program. When it’s you vs the United States of America ..in modern times. Your going down and that’s anyone. When the government brings all they’re resources to bear you can’t win

I would also include Tommaso Gagliano, he is probably the most secretive and low-key boss ever, and was still powerful enough to be in that position.

Louie, you are 1000% correct!.... IF THEY WANT YA, you're done! that's why the smarter guys backed up today. Or in the alternative, only "handle" certain type rackets and activities.

Most importantly, today now more than ever, the only way for possible survival is to keep your head down low! If you think you're gonna go out there and become another Vito Genovese or John Gotti, you can take the "Life" prison term that comes right along with it! Lol.... and that's that as they say!

It is a much different beast than decades before. Both here and in Italy/Sicily as well.

Nonetheless, regardless of the era we choose to speak about, there are always the smart and savvy, more intelligent guys who take a pragmatic approach to "The Life". And then there are the "Bulls in The China Shop", who mostly trudge through the underworld and end up tripping on their own dicks! Lol

Thank

Thank you and hopefully I'll be able to contribute in the future.

Barney did 12 years. OP's criteria: 2. served little to no jail time (or tops 1 moderate jail term)

Correct Neo. There have been many guys who have made tons of money in their lives. But if they did a lot of time, then what good was it? They were better off being shoemakers.

One of my "key" criteria was to have done NO time, or at worst up to a 5-year bid. Otherwise once you start doing 10s and 15s. Or 20, 30 years in the jug. For me? Is most definitely NOT worth it. No matter who the hell they were, or how lofty a position they reached in the hierarchy.

You don't get back those years!

Jo Jo Pecora served 3 years of a 5 year bit in a Federal Pen on a converted horse farm in Lexington Kentucky.
My Dad and I went to visit him and we brought him a big box of "Goomba" Goodies and a box of his favorite cigars, Camacho.
We had no problem bringing it in. The guard took it for inspection then gave it to Joe when he came in the visitation room.
To your point: I told Joe that this maybe wasn't so bad. He told me that if he wanted to go out for a pizza he could do that. He said they took our most precious thing away from him, his freedom. That always stuck with me. So what they say is true: "If you're going to do a crime then be prepared to do the time!"

It certainly goes with the territory....or at least it did. Nowadays with all these rats around, they either never think about it until they are faced with jail and then they flip. Or from the getty-up they know they don't give a damn about "honor", and are gonna sell anybody and everybody out to maintain their freedom!

It is a "NEW" mentality among many of these idiots, and that's why things are the way they are...its the "me, me" generation. Between that and the draconian laws out there today, gangland is a dismal prospect.

PS: Pecora was correct of course. Freedom is precious. Thats the reason why the smarter of the mob set only handled and engaged in certain crimes, not stuff that would bring them 50 years in prison!

Joe took his fall for traveling across state lines to promote illegal gambling. At the time Joe lived in Pittsburgh and drove to West Virginia to operate the Jockey Club.
I know that he along with John LaRocca's help spent plenty of bucks and over a year to get him in the "joint" in Lexington, but certainly still a prison.

My father, as well as my uncle, were in Lewisburg and Atlanta (among a lot of other places). After some years they each ended up in "camps". Believe me it makes a huge, huge difference!

Despite being "inside", you don't have huge steel gates slamming shut on you. Or walking single file in rotation with armed guards hawking and watching your every moment.
You live in dorms with a group of other inmates with a locked door, but NOT a steel jail cell like a cage. Food is better. you have much more freedom to move around the facility. Play ball, stay in the day room, visits, etc.

It makes a world of difference.

Also, although you are serving time with other guys who may have committed serious offenses, it's generally not the same level of hard-core inmate as behind the "wall". Even if they are, by the time they reach the camp they're either older, or on the "back nine" of their bit, and generally don't want trouble. They wanna finish their sentence and get paroled.

Whereas behind the wall you've often got a bunch of lifers or guys doing long terms, who damn well know they're not getting out anytime soon and have a much different outlook. Violence and conflict is much more prevalent. A lot more shit to deal with.

The only part about being in a medium, and especially a "low" facility is that you always run into "rats" and informants because that's where they do their time too. My father and uncle used to get irked by these assholes. They'd chase em away from them. Rats or suspected "cooperators" were shunned from eating or hanging out around them. They would be ostracized by the Italian wiseguys (or any other standup guys) there.

Understandable of course!

Yeah I'd say 5 years in total is the cut off point before it becomes not worth it. May be that's one reason why the mob is having so much trouble finding new talent because young Italians know that if they become part of the life it can end with them doing a long stretch and they have other options. Young Italians can choose professions that don't put them in danger of doing prison time. I mean; do you want to be a bookie or a lawyer?, a doctor or a shylock?, a legitimate business owner or a racketeer? Some of these choices carry prison time and other choices don't.

THAT is the #1 reason why the mob is hurting today. The Italian people have melded into society and today are at the highest strata of income, professions, and the business world. They do not need that anymore. especially when the big profits are not there the way they were in the 1920s through 1980s era, and the penalties for those offenses are way out of whack with such draconian sentences.

Years ago it was potentially big profits with little risk. Today it is exactly the opposite, small profits for huge risk....It's just not worth it any longer.

It's a simple numbers game...and the numbers just don't add up anymore. Only idiots go into the rackets today. Any twenty or thirty some odd year old kid who needs to go that way is kidding himself!

99% have more on the ball than that. Many just don't understand the dynamics of that life until they're in too far, and it's too late.

5 years ok...Joe Arcuri never did time...skipper under Gambino castellano and John Sr. Helped run the family during the 90s and early 2000s

Louie, THAT'S a great pick!!

Giuseppe (Joe) Arcuri is a very underrated mafioso. Why? Because during his tenure in the life, a position that always saw him near the top of power, whether he was a soldier or later a skipper Arcuri was low-key and very cautious.

He lived his life the way a TRUE mafioso should and that is "in the shadows", not a showboat.

He largely stayed out of prison. I'm not even sure he's ever done 1 day in jail. If he did a bit then it was way back in his youth and must have been a short bit at best. But as I say I'm not so sure he's even seen the inside of a cell.

A very well respected man. Close to the bosses regardless of whether it be Salvatore D'Aquilla, Albert Anastasia, Carlo Gambino, or Paul Castellano.

Regardless of his "official" status, Arcuri was a name well known throughout national gangland by those who needed to know. If I'm not mistaken he was utilized to carry messages and the dictates of New York leaders to bosses in other parts of the country. He was also a "mediator" of sorts who was sent to quell disturbances and quarrels between mob factions in different states by the Commission in his earlier years.

I'm sure he wasn't hurting for money. He had interests in several legit businesses in NYC. Just a smart and shrewd guy. If I'm not mistaken he owned a successful retail liquor store on the upper East Side for years, and some real estate holdings. He may not have been a multimillionaire (or maybe he was), but he always earned well.

He also lived to a ripe old age! The most exposure he ever got was during the Gotti era because Gotti was like a magnet for LE. And all those around him had that light shown on them. I do believe your choice more than meets ALL the criteria I set out for a pick.

THATS a pick! Great choice..... One of the true "sleepers" of Cosa Nostra.

I'm not sure with jail Time in his early years but Charles (Charlie the Blade) Tourine was a active guy and big fish and most time under the radar.

His son Charles Tourine jr aka Charles “Chuck” Delmonico was also low key. Died 2008. Im not sure about prison times.
https://therealdeal.com/miami/2015/09/03/mobsters-former-miami-beach-home-listed-for-sale/

If i'm correct Gerardo Catena serving only 5 years. For a Boss not much time.

Charlie the Blade had a wild career, many ups and downs. Lived large but not what I'd consider to be a stable and wealthy guy overall. He had an arrest record a mile long and his fortunes rose and fell many a time.

Yet he was a very well respected guy.
--
Now Jerry Catena? that's another story altogether. Catena was in a category all his own. One of THE wealthiest mafiosi ever. Almost wealthy beyond belief.

With the exception of his 5 year jailing on contempt, and a small bit as a young guy, he mostly served no jail per se.
Very respected. owned tons of major businesses, smart and savvy. NOT an inherently violent guy.

Catena DEF MAKES THE GRADE!

GOOD PICK!!

Thomas DiBella

He was the Official Boss/Acting Boss of the Colombo's (Depends on who you ask) for Carmine Persico.

Think the guy got arrested in the 1930's but he stayed under the radar for decades.

He retired due to poor health; and most likely died a rich man.

Anyone know the extent of DiBella and Persico's relationship? For DiBella to have alot of power in that family means he had to be more then just a fill-in for Persico. They say Persico didn't want Carmine Galante gone but wasn't it DiBella who put in the official vote?

Joe LaForte had tons of real estate in NYC (SoHo in particular) and I can't recall him doing any time. Lived till he was 99.

Tommy DiBella was a VERY important guy. A "sleeper" for many decades. Technically only a soldier, but highly respected.

He was the son of Salvatore DiBella, one of the original founding members of what later became the Profaci Family. So of course his son Tommy was revered.

Low key. Very humble and quiet. A soldier who walked the walk, and talked the talk. So when he was elevated to "Acting Boss", it was because he was both very knowledgeable about the "life", and had NO ambition to grab power.

In truth he could have cared less. THATS why he was selected. Di Bella was no threat and capable.

He was technically a longshoreman active on the Brooklyn docks. He was so old that he had actually been active in alcohol bootlegging during Prohibition.

He was a devout mafioso though and through, and it showed.

He served little if any time. He only had a BS bootleg pinch in the 1930s I think.

I don't know that Tommy had any big money, but it didn't seem to matter to him. He was a good soldier that followed directions.

Joe the Cat La Forte was alleged to be a wealthy guy. He owned several lucrative properties and buildings in Little Italy, and more on SI. He ran numbers for years and was said to have had a solid numbers trade.

Another low key guy who only garnered attention during the Gotti era because of John's high profile, arrogant in your face lifestyle. He exposed all his men to much unwanted publicity.

LaForte, Jimmy Failla, Frankie Dapolito, Joe Arcuri, and many others later all cursed the day he came to power.

IMO Vincent (Vincey) Rao out of East Harlem was another low key powerhouse deserving of making this list.

He had only 5-6 arrests in a career spanning 70 + years.I do not believe he ever did a bit, except maybe, MAYBE a contempt sentence of 30 days (maybe). He was one of the wealthiest guys in the entire Lucchese Family. He owned massive parcels of realty, a vending firm, a mortgage and finance company, a paint company, a huge retail liquor store, and a real estate firm with his brother Charlie.

Vincent Rao was also one of the biggest shylocks in all of NYC for decades. A "Shylocks Shylock", with millions on the street again in partnership with Charlie.

Rao did all this while serving quietly in the capacity as the "official" consigliere of 4 successive administrations: that of Reina, Gagliano, Lucchese, and Tramunti. (and a few interim leaders as well). He also served as the "acting boss" while the boss seat was in limbo on more than one occasion.

A very wealthy and revered mafioso. Known and respected nationally on the Commission and across the U.S.

PS: I almost forgot. He also had a piece of several unions he oversaw for the borgata, and had a solid piece in partnership with Tommy Brown of a large policy-lottery network in E. Harlem.

Here's another low key mafioso who quietly ruled for over fifty years and never served even 1 DAY in the can... Giuseppe (Joe Brown) Lucchese. Tommy's brother.

He was "given" the town of Corona by his brother as a gift. He became the resident "capo" over the entire territory, and was also a very dominant power over neighboring Jackson Heights, Elmhurst, Flushing, Forest Hills, Rego Park, etc, etc. From the 1940's through 1975 he was the man to see in that area.

He ran mostly gambling and shylocking.... ran a very large but quiet crew. Most were never even known to the public.

They made millions upon millions. He lived in exclusive Malba, Queens. His "acting capo" was the better known Joseph (Joey Narrow) Laratro, who still was very low key. NO violence. NO bullshit. NO high profile hijackings, narcotics, robberies, or other rackets that draw police attention.

He held ownership in Whitestone Lanes Bowling Alley, extensive real estate in Queens and the Bronx, a lathing company, etc.

Joe Brown died in his sleep. He was in his mid-80s I believe. He lived a VERY charmed life indeed!

NOT the wealthiest mafioso out there, but he made one hell of a living, and more importantly didn't spend his life in the can or die in the gutter.

Here’s 2 ....Meyer Lansky and His Rabbi Jimmy Blue Eyes... maybe the most powerful Skipper in the Westside during the 1950s,60s and into the early 70s until they sold out to Kirk Kekorian and Teamsters money and the smaller mid west families rose to prominence in Vegas

Jimmy Blue Eyes was a legend. And many don't realize that Meyer didn't carry him, but rather Jimmy Alo was Lansky's "rabbi" as you say.

A VERY well-respected and feared mafioso indeed. In his early life Jimmy did a lot of work. He didn't get there by osmosis lol.

I did an extensive biography on him as well as on Lansky. Visit our website NYMafia and click "Genovese Family" to read them.

..........good pick Louie

Another very successful top guy was Paolo Gambino. He is often overlooked because of his more famous brother Carlo. And thats exactly as he wanted it.

He owned the Blue Star Markets in Flushing, Queens. He also owned Ferro Foods Inc., which was a large Brooklyn based supplier of Italian styled foods to pizzerias and Italian restaurants. He owned several other meat markets in The Bronx and Brooklyn, and was partnered in other ventures through the years.

Paolo had made millions bootlegging alcohol during Prohibition. Even after the repeal in 1931 he continued to operate alcohol stills well into the 1940s and 1950s. During WWII the Gambino brothers became two of the biggest handlers of "stolen gas ration stamps" in the NY/NJ area. Paolo also headed a major "narcotics and alien smuggling" ring for many years.

He was a top "skipper" under during his brothers run at the top. He ran his own crew for over 20 years which had a lot of Italian nationals who were also cut from this low key quiet mold. Many were international heroin merchants. Furture capo and top international narcotics trafficker Pasquale Conte was one of his soldiers. That gives you a little idea of his power.

I don't think he even served 1 day in jail. If he did it was a very short bit(maybe during prohibition)....VERY low key. A real zip!

He was subpeaoned several times before grand juries but thats about as far as it went I believe. He was accused once of monopolizing the "knife sharpening" business in NYC and later sold the firm to the knife sharpening "association" for $177,000. They all chipped in just to get rid of him. The assets purchased? about $800 worth of old dull knives and a broken down truck. Lol

He was a very sharp guy that is not given credit for his position and the moves he made. Mostly because his moves never really came to light!.... now for me THATS a wiseguy!!

He was Carlo's confidante all his life. Paul Gambino was what's called "a sleeper" in the truest sense. He later became known but really flew under the radar all his life.

Carlo Mastrototaro maybe not low-key but a successful mobster. He had network and interest in the whole world. So he made much money. Much legit stuff.

Yes Carlo was def in that category