Anthony (Tony Pep) Trentacosta: The Gambino Family’s Smooth Operator

Anthony (Tony Pep) Trentacosta was a soldier in the Gambino Family who was considered a moneymaker and smooth operator. He preferred to finesse things as opposed to using strong-arm methods.

Anthony (Tony Pep) Trentacosta was born in 1940 in the East New York section of Brooklyn. He moved to 169-11 140th Ave., in Ozone Park, Queens by the late 1960s. He was a documented (inducted) “soldier” in the Gambino Family.

Anthony was primarily involved in gambling (policy), dice and card games, and shylock activities over the years, operating in the Brooklyn, South Queens, and Long Island sections of the NYC.

He started out in a street gang during the 1950s, which was a big social problem of the era.

Anthony (Tony Pep) Trentacosta

In 1956, he was arrested in Rosesale, Queens with 14 other youths, all between 14 and 19 years old, during what police later said was preparation for a “rumble” with another rival gang.

Dressed in the “outfit of the day” (leather jackets, dungarees, motorcycle boots, etc), they were found in possession of “homemade” blackjacks, chains, switchblades, and lead pipes.

They were all charged with weapons possession and unlawful assembly.

Then in 1960, at age 20, he and another man named Alfred DiMichele were arrested on burglary charges after police caught them in a Woodhaven, Queens bar located at 87-01 91st Ave., after closing, attempting to steal several cases of whiskey.

They had tripped a silent alarm alerting the cops.

By the mid-1960s, he had advanced to more sophisticated activities.

In 1966, after a police raid on an Ozone Park apartment located at 137-20 Lafayette St., which was where Trentacosta lived at the time, he was arrested with Gambino soldier Anthony (Tony Lee) Guerrieri on gambling charges for operating a $3,000-a-day “numbers” ring.

They were found in possession of 120,000 policy slips, two adding machines, $1,863 cash, 150 envelopes holding the policy slips, and a loaded pistol.

Police had been watching the pair for several weeks before obtaining a search warrant.

Trentacosta was additionally charged with gun possession.

He was a close associate of Anthony (Fat Andy) Ruggiano, who is believed to have been his first capo.

For years, he operated a private mob social club in the Franklin Square area, where he operated weekly high-stakes card games.

He became close to Carmine Fatico, John Gotti, and others in that regime which was originally based out of his East New York neighborhood and had relocated to the Ozone Park section.

Fatico ran the Bergin Hunt & Fishing Club, a notorious mob social club on 101st Avenue in Ozone Park.

In 1977, out in the Huntington section of Suffolk County, Trentacosta became involved in an investigation into “floating crap games” being run by several of his close associates, including John (Johnny Boy) Ambrosio, a mob associate who in later years would be inducted and rise to capo status.

Brought before a grand jury to answer questions, he was indicted for contempt after refusing to testify.

Anthony was one of many arrested during a gambling raid on a Mulberry Street gambling den in 1980.

It was a high-stakes “dice game” that drew all the underworld’s glitterati. Because of the top mobsters detained, the story ran in all the newspapers of the day.

Trentacosta had an arrest record starting from 1956 for weapons possession, unlawful assembly, burglary and possession of burglar tools (a screwdriver and tire iron), policy, possession of policy slips, possessing a gun, operating a dice game, criminal contempt of court, racketeering, and racketeering conspiracy.

By the mid-1980s, he was officially “made” into the Gambino Family.

He operated his own crew of associates, using his Franklin Square social club as a base. He served under capo Peter Gotti.

Soon, he expanded activities, investing in a chain of bagel stores in Manhattan.

He also became engaged in the “gasoline bootlegging” racket, a massive tax evasion scheme involving all five NY Families.

Trentacosta became the “point man” and overseer for the Gambinos in partnership with a friend, soldier Alex (Black Alex) Morelli.

By all accounts, “Tony Pep” was earning big money for himself and his crime Family.

He was considered a “moneymaker” and smooth operator who preferred to “finesse” things as opposed to strong-arm methods used by many of his mob brethren.

As though he didn’t have enough operations in play at this time, another major moneymaker fell into his lap.

He became acquainted with a young man by the name of John Porcaro (who years later would disappear forever), who with several brothers, operated several large moving and storage firms.

First in NYC, then relocating to South Florida, Porcaro was a very astute businessman, but also a tremendous scam artist.

He ran these various companies in a “wild, cowboy” fashion, scamming the public while making millions of dollars, then closing or bankrupting the firms, only to open up again under a new corporate name.

Father & Son Moving-Storage, Nice Jewish Boy Moving, Family Moving Corp., were just a few of many such firms.

Trentacosta became his “rabbi” and protector. A schemer such as Porcaro needed a protector against his many enemies.

He “gave” Tony Pep his own moving and storage firm in Atlanta, Georgia, to operate, and made him a “full” partner in all his operations.

So much money was generated by the approximate 20 or so moving firms he ran, that Pep decided to move down to Georgia where he bought a mansion, acquired his own stable of horses, purchased large tracts of land to develop, and rode around in a $250,000 “Corniche” Rolls Royce.

Tony Pep was becoming a “country squire” and loving every minute of it!

There was so much law enforcement “heat” back in New York City on the Gambino Family (largely generated by Gotti peacocking around like a movie star) that his move south was a perfectly timed exit and reprieve from all the hustle and pressure of that era

Before long, the Gambino administration asked Trentacosta to oversee their rackets being run in the Florida area (Fort Lauderdale and surrounding towns).

He would split his time between Atlanta and Ft. Lauderdale as required, picking up a girlfriend (comare) or two along the way for a little extracurricular enjoyment while away from home.

But some of his associates were less than savvy or experienced mob denizens, “loose cannons” would be a better analogy for them.

Namely, Freddy Massaro, a transplanted New Yorker was his main affiliate.

Massaro thought he had become another “Al Capone” under Tony Pep’s wing, and started running foolish and dangerous scams (check frauds, prostitution, drugs, etc), and took into his confidence low-caliber street urchins.

Before long, he and some associates were indicted for the murder of a topless dancer and other crimes.

The FBI indicted Trentacosta as well.

Although he actually had little knowledge or involvement, but as their superior, he was tainted and connected by the conspiracy laws.

They were all tried and convicted in federal court down in Ft. Lauderdale and sentenced to prison.

Massaro received life and Tony Pep received eight years.

He died in 2005 in federal prison while serving his sentence....Tony Pep was only 65 years old.

Until next time..."The Other Guy"

Anthony (Tony Pep) Trentacosta: The Gambino Family’s Smooth Operator

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Colombo/Gambino Mobster: Lawrence (Larry Baccala) Abbandando

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