Colombo Associate Charles (Ruby) Stein: The Mafia’s Biggest Loanshark Loses

Charles (Ruby) Stein was arguably the single biggest shylock in New York City during the 1950s to 1970s era.

At one point, he was reputed to have over $5,000,000 “on the street” on any given day.

When he partnered up with Colombo soldier and later capo Nicholas (Jiggs) Forlano , the dynamic duo became almost unstoppable even when the Gallos tried killing them several times during the Profaci-Gallo War of the 1960s .

But as sometimes happens in the underworld things take a turn for the worse, and that's exactly what happened to Ruby Stein.

Ruby Stein - Early Life

Charles (Ruby) Stein was born in 1915 in NYC. In his youth, he may have been a semi-professional boxer.

Stein started out as an independent until the early 1950s when he was approached by Nicholas (Jiggs) Forlano, a soldier and later a capo in what was then the Profaci Family of Brooklyn.

Ruby Stein

The two became partners since no independent could operate at such a high level without mob connections.

“Ruby and Jiggs,” as they became known, handled mob funds generated by not only the Profaci Family but also several other Families who contributed to their “bankroll.”

Stein also utilized money invested by otherwise legitimate business people as a source of funds.

Ruby Stein lived for many years in the Jackson Heights, Queens area while Forlano lived in neighboring Astoria, Queens.

The dynamic duo also was very heavily engaged in gambling operations , controlling several large-scale bookmaking combines (horses and sports).

Stein was said to have a near mathematical memory, able to retain all numbers, figures, and related interest and outstanding balances in his head. This eliminated the need for usury and gambling records which helped him avoid prosecution.

During the 1960s, the dynamic duo also operated a race-wire service through several Jewish associates charging area bookmakers a weekly fee for this service.

With the advent of tensions and the ensuing violence during the Gallo-Profaci war, Forlano became a central figure and interim leader of the breakaway Gallo faction.

Several attempts were made by the Profacis to win Forlano, and ultimately Stein, back into the Family fold, and the millions they controlled.

Major Targets

Once Forlano went back into the Family, he and Stein became major murder targets by the Gallos. Several murder attempts were made against Forlano, including shooting at him near his Astoria home.

The Gallo gang also attempted to kidnap Stein off a Manhattan street corner and only Stein’s screaming, punching, and kicking at his assailants prevented his kidnapping and/or murder.

Ruby Stein's partner, Jiggs Forlano

In 1953, Stein served a prison term on an income tax evasion conviction related to his gambling profits.

In 1961, Ruby Stein, Forlano, and 14 others were arrested at the White Turkey Restaurant on 57th Street and 2nd Ave. on consorting with criminals charges.

According to police, the arrests broke up what they referred to as a “mob powwow” of top gamblers across the city.

In 1964 Ruby and Jiggs were charged with felonious assault and attempted extortion of an actor who couldn't pay back a $6800 loan. Actually, authorities charged them with "auditioning" the actor as he was trying to explain why he couldn't pay back said loan.

After Stein punched the actor in the face, Jiggs told him he'd break his arm he didn't come up with the cash ASAP.

"I won't do it now," Jiggs told him. "But I'll break it in a few days if you don't get the money."

Instead of paying them back, the actor went to the cops.

At that same time, Ruby and Jiggs were pulled into a state investigation hearing about the loanshark racket in New York City.

Ruby and Jiggs pled the fifth 22 times between the when investigators asked about their loansharking operation.

As an interesting sidenote, the Gambino Family's Carmine Lombardozzi was also called into this hearing. He took the fifth 18 times.

By all accounts, Ruby and Jiggs were riding high during this period. Ruby was considered the “brains” while Jiggs was the “muscle” in their partnership.

But Jiggs was a bad, degenerate gambler who spent large sums of money at area racetracks and on betting himself with other bookmaking offices.

Scheming for Money

Always in need of money, Forlano eventually turned on Ruby.

In 1965, Stein was once again indicted for tax evasion, convicted, and sent to federal prison.

While Stein served his prison term, Forlano was supposed to oversee their operation and bankroll. But by this time, Ruby’s relationship with Jiggs had taken a turn for the worse.

Ruby Stein no longer fully trusted his long-time partner…. and for good reason.

Ruby Stein sneers at reporters after an arrest.

Jiggs had approached his boss Joe Colombo , and they schemed to burglarize and/or otherwise “set up” Ruby to rob a suitcase said to house a huge cash reserve of money Ruby owned.

Subsequently, Ruby got wind of this scheme, took proper precautions to safeguard his funds, and immediately broke up the partnership.

In the following years, Ruby would affiliate himself with Fat Tony Salerno and the Genovese mob . He also allegedly partnered with Genovese power Carmine (Little Eli) Zeccardi.

A Costly Mistake

Despite this transfer to the powerful Genovese mob, Stein also befriended an Irish mob figure by the name of Jimmy Coonan, an alleged boss of the westside gang known as “The Westies.”

Stein utilized Coonan as a young protege, loaning him money to run his own loanshark business and using him on collections.

But Stein miscalculated this time....badly!

Rather than pay the shy money due Stein, Coonan chose instead to shoot him in the head one afternoon and thereafter “behead” him, severing Ruby’s head from his torso.

Several weeks later, Stein's remains washed up on Jamaica Bay in New York. This was in 1977. Ruby Stein was 62 years of age.

One final note. By the mid-1960s, Jiggs Forlano had relocated to South Florida. He had a massive heart attack and died one afternoon doing what he enjoyed doing best….he was felled at the local racetrack! He was also only 62 years old.

And that's the end of the saga of “Ruby and Jiggs.”

Colombo Associate Charles (Ruby) Stein: The Mafia’s Biggest Loanshark Loses

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Colombo Associate Charles (Ruby) Stein: The Mafia’s Biggest Loanshark Loses

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Racketeer Snapshot: Lucchese Family Soldier Carlo Piccioli

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