How to Catch A Criminal: Agent Wiseguy

June 15, 2021
Jack Garcia, the big Cuban from the Bronx, would become Jack Falcone, a third generation Italian American who made his name as a jewel thief and extortionist with connections in Florida.
Since the early 1900’s, the Federal Bureau of Investigation has taken down the most high profile criminals including Bonnie and Clyde, Al Capone, Lee Harvey Oswald, Timothy McVeigh and plenty more. The FBI has conducted countless operations focused on bringing down anyone who threatens the American way of life; be they spies, terrorists, bank robbers or organized criminals. For decades, crime’s biggest enemy in the U.S. has been the FBI and its agents. Often romanticized in film and TV with shootouts and covert operations, the FBI’s work is generally investigative in nature. On occasion, however, real life cases put Hollywood to shame.

Born in Havana Cuba in 1952, Joaquin Garcia fled Fidel Castro’s rule with his family when he was 9 years old. They set up their new life in the Bronx, New York. While his parents planned to return to Cuba when Castro was gone, that day never came. Joaquin, or Jack as he came to be known, grew to be 6’ 4” tall and over 300 pounds, making him a football standout in high school. Jack received a football scholarship to attend the University of Richmond in Virginia, where he graduated in 1975. While in school, Jack was riveted by Al Pacino’s performance in the movie Serpico. This depiction of the cool undercover cop living in the city, the pretty girlfriend, the fast motorcycle and outing the bad guys became his dream. After looking into multiple police departments and finding no one was hiring, Jack applied with the FBI. Unfortunately, he never heard back. Some time later, Jack saw an FBI recruitment commercial on Spanish TV. The commercial implored fluent Spanish speakers to apply. Thanks to his Cuban roots, Jack was exactly what the Bureau was looking for. He called the number and mentioned he had already applied. The recruiters found he was the perfect candidate, but had been disqualified because he was not a U.S. citizen; a hurdle Jack would soon overcome.

Once a naturalized citizen, Jack reapplied, was hired and headed to Quantico for training. In 1980, his 26-year FBI career began; 24 of which were spent conducting more than 100 undercover operations. He started at the Newark FBI Office and later Philadelphia, taking down Cuban terrorists, Colombian cartels and other criminal organizations. With two decades of undercover work as a money launderer, drug trafficker and thief, he was approached with what would become his greatest role.

The Gambino crime family, formerly the Anastasia crime family, was founded by Vincent Mangano sometime in the 1910’s. In the 1950’s, Carlo Gambino assumed control and took the family from minor players to the most powerful organized crime family in the U.S. Engaging in loan sharking, gambling, car jacking, robbery, prostitution, extortion and more, times were good for Gambino and his cohorts. After Gambino’s passing in 1976, control of the family was left to his brother-in-law, Paul Castellano, who was murdered and succeeded by John Gotti. Gotti was convicted of murder in 1992 after another member of the family, Sammy the Bull Gravano, cooperated with the FBI. Gotti died in prison in 2002, ending the golden age of the Gambino family. Also in the early 2000’s, Greg DePalma, a Gambino captain recently released from prison, was looking to make money like the old days. His crew was working in conjunction with Albanian mobsters to shake down strip clubs when the FBI was tipped off about their extortion efforts.

Jack Garcia, the big Cuban from the Bronx, was to become Jack Falcone, a third generation Italian American who made his name as a jewel thief and extortionist with connections in Florida. His job was initially to act as a business partner to one of the strip club owners and make the protection payments and establish which gangsters were responsible for the extortion and learn as much as he could about their business. To be convincing in his role, Jack underwent intensive mobster training from FBI Agent Nat Parisi. Parisi, an Italian American, taught Jack the ins and outs of a “wiseguy.” No more wallets, carry your cash rolled up in a rubber band. Pronounce the name of Italian food authentically, or you’re dead. Wear fine Italian suits, diamond rings and expensive watches. Drive a fancy car and flash your money. Look, sound and act, like someone who is part of the life. Make the real mobsters wonder who this guy is and how he gets his money. Jack’s large presence and charisma made him well liked by the goons who picked up the money.

As the payments continued and the business relationship between Falcone and DePalma’s crew became more friendly, Jack got close to the captain himself. DePalma had no use for someone who couldn’t make him money, and Falcone had access to an endless supply of expensive goods and cash seized by the FBI from other cases. Jack presented DePalma with a load of counterfeit cigarettes for his birthday, piquing DePalma’s interest in Falcone as an earner. DePalma kept Jack and his high-dollar “stolen” goods close, always getting his taste from the scores. In reality, Jack’s scores were more undercover work in other parts of the U.S. He worked as many as five cases concurrent with the Gambino Family case. He would tell DePalma he was headed out of town for a lucrative opportunity, work the other cases, bust the other criminals and head back to New York with an envelope full of cash. DePalma became so enamored with Falcone that he made him his personal driver.

As he got deeper into the lifestyle, Jack had to formulate an emergency escape plan, just in case he got in too deep. If he was tasked with participating in a murder, his plan was to collapse, feigning a heart attack, made even more believable by his near 400-pound frame. Once the other mobsters got him to the hospital, he would make his final escape. Luckily it never came to that and for two and a half years Jack Falcone wore a recording device and learned all he could about the Gambino Family and its earnings. Falcone made himself such a loyal soldier and earner for DePalma, he was told he was in consideration to be a made man. This honor is reserved for Italians only.

Things took a turn when DePalma brought Jack along for a meeting with Peter “Petey Chops” Vicini. Petey Chops had been a problem for the Gambino Family for some time. He failed to “kick up” or contribute part of his earnings to the head of the family, Arnold Squitieri, repeatedly despite his profitable ventures. DePalma was tasked with collecting from Petey Chops, who made excuses every time they were supposed to meet. To drive the point home that it was time to pay up, DePalma also brought along acting captain Robert Vaccaro. DePalma, Vaccaro and Falcone tracked Petey down in a department store in White Plains, New York. Petey, already on thin ice, became belligerent after being confronted. The situation came to a head when Petey was knocked unconscious after Vaccaro struck him with a candlestick he pulled off a shelf. When Petey awoke, covered in blood, he demanded to know why he was attacked. The answer came in the form of a fist to the face from Vaccaro, once again knocking Petey out. Jack ushered DePalma and Vaccaro out of store and away from the area before police arrived.

Not only was Jack shocked by what he saw, he was now nervous. In mob life, if there is a beating given, it’s your duty to take part. Rather than jump in, Jack played peacemaker, taking the candlestick away from Vaccaro and separating the parties before it escalated. Something a cop might do. Afterwards, Jack noticed that he was looked at differently by his fellow mafia members.

With Garcia in danger of being made, the FBI made the decision to end the operation 16 days later. Though Garcia wanted to become a made man and topple the entire family from the inside, the risk had become too great. Using the years worth of information gathered by Agent Garcia, the FBI brought charges against 32 members and associates of the Gambino Family and 31 of them pled guilty. The one man to take his case to trial was Greg DePalma. After Garcia testified, DePalma muttered an expletive at the man he thought he knew. He was found guilty and sentenced to 12 years in prison, where he died in 2009.

Jack Garcia retired from the FBI in 2006, and maintains a public image despite the alleged contract on his head. He believes it is important for him not to be in hiding, as it shows others who might testify against the mob they do not need to be afraid.  

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