During the years spent at the summit of their respective families, in your opinions, which of these legendary New York bosses became the wealthiest?

A) Francesco (Frank Costello) Castiglia
B) Albert (The Executioner) Anastasia
C) Giuseppe (Joe Bananas) Bonanno
D) Giuseppe (The Old Man) Profaci
E) Gaetano (Tommy Brown) Lucchese

Probably the one who left tons of cash to his two families, meaning his blood family and the "other one". Lucchese?!

My guess is Costello, even though he retired earliy, he was defintiely wealthy. If not him, I would say Lucchese.

There's a story of Tommy Lucchese taking out a big fat bankroll from his silk pocket and peeling off $12,000 and giving it to his doctor who was treating him for cancer. This was in the 1960s, so yeah, you do the math. Tommy Lucchese is my all-time favorite mob boss by the way.

With today's cost of living the way it is, for today's mob bosses to be living nicely they have to be making some serious loot as well.

Profaci's family is still reaping the benefits of his wealth from the olive oil business. I'd go with him.

There is a lot of merit to what you just pointed out BT. A lot of merit.

Both of them are also good picks IMO. Both were enormously wealthy, especially Costello (like next level wealthy.)

That's my choice as well Big Tuna. The guy left a huge legacy.

I'm in good company!

Yes, you are BT. I gotta agree with ya 1000% on that! LOL

They were all multi millionaires, dificult to say but Genoveses and Gambinos were the richest families.

while merely only an acting boss, JERRY CATENA was certainly well heeled !

Genoveses in those times were worth billions.

Catena was official boss for a little bit

My vote goes to Louis (Lepke) Bucholter, who had a conglamorate in the Garment District, trucking, movies, bakeries, etc.

Nice pick TB, and when was no longer in the picture, the Genovese and Lucchese families swooped them up.

Frank Costello is my vote, what he was bringing in across the country and other countries with Gambling and casinos made him a lot of money.

While Catena wasn't one of the guys I listed, I have to say that Catena was, as you say, extremely "well heeled." Very much so. In fact, Catena was one of the wealthiest (most successful and most powerful) guys around, bar none.

And although Catena never became the "official" boss of the old Luciano/Genovese Family, he had been a close intimate of that Family's NJ hierarchy since the 1930s era, and even before that, he dated back to the days of NJ rackets boss Longy Zwillman.

In later years, as a clear sign of how trusted his was for his moneymaking abilities, temperament and loyalty, Vito elevated him to "acting boss" as his eyes and ears over the membership and to steady the ship after Genovese was jailed for narcotics.

Jerry Catena was SOOOO wealthy and happy where he was, and the station he had in life, that as he aged he actually shunned the thought of becoming the official boss. So he migrated down to South Florida and essentially retired. After all, what did he need at that point?

Smart man! In fact, one of the smartest IMO.

Well, what can you say. Lepke controlled a lot until he got fried. And, as you mentioned he had a lock on a lot of varied industries. After his demise Lepke's "assets" were parceled out among the Five Families. (I have no doubt thats one of the reasons why he was set up. In order to eliminate him and grab his rackets.)

Including some of the narcotics trade/connections because Lepke was allegedly deeply involved in it.

Correct TD...100%

He was an official boss. There’s many files that list him as a former boss.

I cant forget the old days on these forums when some posters had "hardcore" belief that the Mafia never dealt with drugs lol, especially about Chicago lol. After awhile they became silent and some even became like "I told you they were dealing drugs" lol lol

Well, I wasn't around back then, so I don't know who the culprits were, but I suspect its a case of "Monday morning quarterbacking." Lol

Good one lol

i remember from one past t.v. program on LEPKE, it was alleged he was making 5 million a year in the 1930's from his rackets.it was also stated the LUCCHESE was also earning 5 million a year during the same time frame.

the alleged numbers for COSTELLO during prohibition were staggering. its believed he made 50 million during prohibition. a truely ungodly amount of money for that, or any era.

i dont think we can leave out TONY SALERNO either. while he may never had been more than the front boss his wealth is legendary.

Faffy, I completely agree with you. On everything you said. And yes, Fat Tony had money he never even counted yet. lol

FAT TONY had a lot of guys to count his money. while all of the families had major, major earners, it seems like the GENOVESE had a ton of huge earners.dont forget RICHIE THE BOOT, or MATTY THE HORSE, or FUNZI TIERI. DON VITONE wasnt too shabby either !

No doubt about that. But where do you draw the line with the question? Ya know what I mean? Because, truth be told, there were lots of guys who became very wealthy. Thats why I just named those five NYC bosses for the opinion piece.

I’m going with Joe Profaci ….