Who Was the Wealthiest Gangster?

There have been many wealthy gangsters over the years, but Button Guys recently posed a question to our YouTube community asking this specific question about the "Golden Era" of the mob in New York City:

During the years spent at the summit of their respective families, in your opinion, which of these legendary New York bosses became the wealthiest? The choices were (in order of the poll) Francesco (Frank Costello) Castiglia, Albert (The Executioner) Anastasia, Giuseppe (Joe Bananas) Bonanno, Giuseppe (The Old Man) Profaci , Gaetano (Tommy Brown) Lucchese.

As usual, there were many interesting answers to this question. But what does Button Guys think? "The Other Guy" offers his opinion.

Admittedly, this was another very tough question asked and a very tough choice to make. Because each of these fellas earned very well during their many years in the mob, and I have no doubt that each of them made many millions during their lifetimes.

But, let’s face it fellas, you don’t come to Button Guys to be coddled, do ya? Of course not! You come here to be challenged and to learn more about Cosa Nostra. Am I right?

So, with that said, here is my humble opinion about the wealth of the five bosses listed.

Francesco (Frank Costello) Castiglia

Frank Costello was, without a doubt, one of the wealthiest and most accomplished, if not THE wealthiest and most accomplished, mafioso to ever operate within the United States.

He became so wealthy and had such vision, that during his career, he invested his vast wealth into buying not one skyscraper (which would have been an unbelievable feat in and of, itself) but multiple skyscraper buildings in Lower Manhattan from 79 to 89 Wall Street in the “Financial District.” and multiple buildings from 148 to 152 Pearl Street, both Manhattan. These skyscrapers, of incalculable wealth, were and are among the most prestigious and expensive pieces of real estate in the entire world.

For many years, Frank resided in a luxurious apartment in one of the most prestigious buildings in midtown Manhattan, at 115 Central Park West (Apt 18F.) He owned a second residence as well, a sprawling multimillion-dollar estate located at 5 Barkers Point Lane, in the exclusive waterfront community of Sands Point, Long Island .

Frank Costello

He also held public and hidden ownership interests in numerous other valuable properties and businesses throughout Manhattan, its outer boroughs, and Long Island, including the world-famous Copacabana Nightclub, The Stork Club on 53rd Street, and other Manhattan nightclubs as well as several Las Vegas casinos, through hidden ownership points like The Flamingo Hotel & Casino, The Frontier Casino, and many other legitimate businesses throughout the U.S.

During the Prohibition era, he was known as one of the largest and most successful bootleggers. And, in time, he became the top liquor smuggler from Europe, securing the exclusive franchise for the popular Kings Ransom Scotch.

Later, he became the sole owner of the William Whitley Distillery in Scotland, the manufacturer of Kings Ransom and House of Lords Scotch Whiskey, buying out the previous owners of record in a multi-million dollar deal. In later years, it was said that he secured additional franchises for several other top brands. These and other ventures made him a multi-millionaire many times over by the end of the Prohibition era. During this same era, he was also known to smuggle large caches of diamonds into the U.S. from overseas.

It was a vast fortune, incalculable in mere dollars and cents...and Frank was just getting started!

From 1933 through at least the mid-1960s, Costello was the sole owner of the Hills Vending Co. of Chicago, Illinois. This was one of the largest manufacturers and distributors of slot machines in America. He placed these machines all over New York City and the Tristate area while handling distribution through a second vending company he created named the Midtown Novelty Company of NYC.

After then-Mayor Fiorello LaGuardia started cracking down on Costello’s machines, he seamlessly pivoted and moved thousands of his “one-armed bandits” down to Louisiana, where he went into partnership with New Orleans boss Carlo Marcello. They opened up the Pelican Novelty Company, taking in Costello’s assistant, Phil Kastel, as a junior partner to keep watch over their operation. This company later became known as the Louisiana Mint Company and was said to be one of the largest coin-machine companies in the United States.

He reportedly held a hidden interest in the Roosevelt Raceway Harness Track in Westbury, Long Island., etc., etc., etc. There seemed to be no limit to Frank’s ambition and abilities.

Costello was said to have kept control over his vast rackets, as well as that of the New York Mafia, by maintaining a vise-like grip over a good majority of New York’s politicians and glitterati through his control over NYC’s Tammany Hall political machine. In fact, he was considered the “unofficial” kingmaker among New York politicians. Legions of city and state judges, prosecutors, county attorneys, top brass in the NYCPD, and even congressmen and governors were known to capitulate to Costello’s demands and jump at the very snap of his finger.

Albert (The Executioner) Anastasia

Although Albert Anastasia was a major hoodlum and an active racketeer for decades, it wasn’t until 1951 that he was catapulted to the top rungs of the Mangano Family as the new boss, after orchestrating the disappearance and presumed murder of previous boss Vincent Mangano.

Only six short years later, in 1957, Albert would meet his fate in the barber’s chair. So, he had a very short rein as the actual “boss” of the Family as opposed to some of the other bosses named who ruled for many decades.

Albert Anastasia

Yet, there is no doubt in my mind that Anastasia earned many millions of dollars over the course of his time serving as a top capo and as underboss before, ultimately, becoming boss of this large borgata.

He had his fingers in a lot of lucrative rackets not the least of which was his ironclad control and domination (since at least the 1930s) of Brooklyn’s dock rackets through several key international Longshoremen’s Union locals he and his brothers ran, and later, over the Staten Island waterfront union rackets as well.

The waterfront piers and docks were where the Anastasio brothers first made their mark and it always remained their base strength. Dock unions such as the notorious Local #1814 and several others filled Albert’s pockets for years. It was so lucrative for Anastasia that he installed his brother, the notorious “Tough Tony” Anastasio, as undisputed leader over the Brooklyn waterfront to watch his interests.

As one of NY’s most important Mafia leaders, no doubt he had his fingers in dozens of other racket pies as well. But, at the end of the day, Anastasia was a hoodlum with a hoodlum’s mindset. He was not a “businessman” type mafioso. So, he never focused on achieving extensive legitimate interests. He was happy to roll up his sleeves and roll around in illegal rackets.

Spoiler Alert: It was also reported that Anastasia was also a lifelong inveterate gambler. That said, If true, would have greatly reduced his ability to save money, and ultimately, to build and accumulate the kind of awesome wealth that some of the more conservation and prudent bosses did.

So, IMO, after he died, Anastasia probably left some sort of bankroll for his blood family. But, once again, not anywhere near the type we’re discussing here.

So, for all the reasons enumerated above, Albert Anastasia doesn’t make the grade or rank as the wealthiest, or even one of the wealthiest, Mafia bosses.

Giuseppe (The Old Man) Profaci

Now THIS man was deceptively wealthy! And notwithstanding what many history books and mob historians generally write about him discounting his power and standing within the underworld, for various reasons, Profaci was the man!

Most people don’t realize that Joe Profaci was one of the “original” bosses of the Five Families and an “original” Commission member (and one of its founders) since the very formation of the infamous Mafia Commission in 1931.

Even before that Profaci ranked as one of the top bosses of the strictly “Sicilian” Mafia in the United States before the rules were changed allowing Calabrians and Neopolitans to join the Mafia’s ranks as well. So, he was always powerful.

Joe Profaci

And aside from his tremendous abilities as a mafioso, Joe Profaci was also one of the most astute and savvy “businessmen” around. In fact, his business acumen is legendary.

He owned an expensive brick home in the Bay Ridge-Bensonhurst section of Brooklyn, NY. He also owned a palatial 328-acre estate in Hightstown, New Jersey . He owned a third vacation home in Miami Beach, Florida.

Over the course of his career, Profaci accumulated one of the greatest wealth of any mafioso or rackets boss in the United States and Italy too, for that matter. His borgata’s far-flung racket operations brought in untold millions of dollars annually by themselves.

But, when coupled with the myriad of legitimate business holdings Profaci and his blood family also owned and operated or controlled, the financial numbers become truly staggering.

To form a complete list of all the legitimate businesses Profaci owned and the wide range of industries he influenced would be a monumental task because this man was a financial wizard and dynamo. But what follows are some of his businesses and accomplishments.

He actually cornered the market in various industries…

OLIVE OIL IMPORTS: Dating to at least the 1930s, he had established himself as an olive oil importer and wholesale distributor. He eventually became one of the largest importers in the country. He owned the Sunshine Edible Oil Company, Mamma Mia Olive Oil Company, Santuzza Oil Co., and held major interests in such other companies as the world-famous Filippo Berio and Fratelli Berio Olive Oil Companies. Nowadays, Joe’s descendants control the popular Colavita Olive Oil Company.

Through another division of the Mamma Mia Importing Company, he was later acknowledged and widely recognized as the largest single importer of tomato paste and products to the United States.

He eventually handled all areas of this business, operating as a manufacturer, canner, and wholesale distributor not only of tomatoes and olive oil but also a variety of other food products.

Years later, Mamma Mia eventually morphed into Roma Foods, Inc., a massive wholesale supplier and distributor of mozzarella, canned tomatoes, olive oil, meats, paper products, and hundreds of other Italian products to restaurants, pizzerias, and catering halls throughout the entire eastern seaboard and midwestern United States (they supply their products to over 25 states.)

Side Note: To this day, Roma Foods has a “lock” on the distribution of the famed Grande Mozzarella Cheese (which was owned by boss Joe Bonanno,) the acknowledged leader in mozzarella supplied to pizzerias throughout the country.

LIQUOR DISTRIBUTORSHIPS: Alpine Wines & Liquors, Inc., Peerless Importers, Inc., and several other wholesale liquor companies (within an interlocking series of firms) which have enjoyed a virtual lock over the sale and supply of liquor to restaurants, bars, and nightclubs since Prohibition.

LINEN-SUPPLY: Arrow Linen Supply Company was, and to this very day still is, one of the largest and most popular linen-laundry and supply companies to restaurants, nightclubs, butcher shops, and many other types of businesses in the NYC metropolitan area. United Uniform Corp., is another linen supply firm he held ownership in.

REAL ESTATE: Owned dozens of valuable properties and commercial buildings that collected rents in NY, NJ, and Florida.

GARMENT MANUFACTURING: Owned several large, lucrative dress factories in the tristate area such as Newburg Coat Co., etc.

...AND MORE: And this is just a “short list” of the many business ventures Profaci dabbled in over the years. Upon his death in 1962, his considerable assets were bequeathed to his children and relatives who still operate them today.

Giuseppe (Joe) Profaci, was, without a doubt, one of the wealthiest mafiosi to ever operate, anywhere!

Giuseppe (Joe Bananas) Bonanno

This man was another financial powerhouse. Not only within the Mafia itself but within the upper world of legitimate business as well. During his career, he accumulated outright ownership or partnerships in many lucrative businesses, including, but not limited to the following:

Grande Cheese Company: To this very day, the acknowledged leader and “gold standard” for mozzarella cheese and other cheese products sold to pizzerias and Italian restaurants throughout the United States. Based in Wisconsin, this firm is considered one of the largest and most important cheese suppliers. I don’t have the figures on their annual gross revenue, but I’m sure it would make your nose bleed.

Saputo & Sons Cheese Corporation: Based in Canada, Saputo and Sons is the Canadian equivalent to what Grande is in the U.S. They are a massive and very profitable cheese supplier. A multi-multimillion dollar business annually.

Joe Bonanno

Other businesses: Joe Bonanno was a businessman of epic proportions. And aside from the cheese industry, during his lifetime, he invested and became partners in a wide variety of businesses, including vast tracts of land in Upstate NY, the midwest, and elsewhere; a cotton farm; numerous garment manufacturing firms; several funeral homes; insurance firms; etc., etc.

Joe Bonanno, was, without a doubt, one of the most accomplished mafiosi in legitimate business, and, as a result, one of the most financially successful and wealthy mafiosi ever!

Gaetano (Tommy Brown) Lucchese

Another underworld powerhouse who focused on “legitimate” business in addition to the many lucrative rackets his Mafia Family enjoyed.

Lucchese became one of the most powerful figures in New York’s garment industry, which, by extension, made him one of the most powerful garment racketeers in the nation. Sharing power with the Luciano/Genovese Family, “The Garment District” was essentially his for the plucking.

He either owned outright with his name on the incorporation papers, or controlled hidden ownership interests through dozens of his minions, upwards of a hundred or more dress and garment manufacturing firms. Not only in NYC but also in New Jersey, Pennsylvania, and elsewhere in the U.S.

Couple that with his ownership interests in several “hoisting companies” that enjoyed a virtual lock over NY’s construction industry, various construction companies, bowling alleys, real estate, restaurants, and nightclubs he was alleged to have invested in, and you can easily see why Tommy Lucchese ranks into the top tier of this poll.

Tommy Lucchese

Like Costello, Lucchese’s deep infiltration into the world of politics and politicians, and his control over much of NYC’s police department, greatly helped him in his business and racket endeavors.

He was a millionaire many times over. And he was definitely one of the wealthier mafia bosses to ever operate. So it’s a real tough choice because he’s definitely up there among the best.

But, in the end, even Tommy, in my opinion, doesn’t rank as high as a Costello, Profaci, or Bonanno for the ultimate and continuous generational wealth they were able to achieve.

Final Results

Now it’s time for me to choose who I believe to be number one, two, three, etc. in the pecking order of wealth. So, may we get a drum roll, please. Here goes….

For different reasons, I rank Frank Costello and Joseph Profaci the same, listing them both in a tie for number one. After that, I rank Joe Bonanno as number two, Tommy Lucchese as number three, and Albert Anastasia comes in last place at number four.

So there you have it folks. For better or worse, these are my “opinions” about their overall wealth.

I hope you enjoyed this post.

Yours truly…”The Other Guy”

Join in on conversations like these at our Mob Fireside Chat channel on YouTube. Wanna offer your opinion on THIS opinion? You can do so on our newest Community Post here .

Who Was the Wealthiest Gangster?

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