Joaquin “Jack” Garcia

Born: 1952, Havana, Cuba
Nicknames: Jack Falcone (undercover name)
Associations (undercover): Greg DePalma

Before he succeeded in infiltrating New York’s Gambino crime family for years, undercover FBI special agent Joaquin “Jack” Garcia first had to go to school. He went to the FBI’s “mob school,” where he received an education in how to hit the ground running with veteran mobsters. His teacher was special agent Nat Parisi. “First off,” Parisi said, “don’t carry a wallet.” Wiseguys carry wads of currency, often bound by the kind of rubber band that grocery stores use to keep broccoli together. Also, the correct pronunciation of Italian food matters — as Tony Soprano would say. Those long pasta shells are not “manicotti,” they are “manigote.” Another valuable lesson he learned is that mobsters love compliments. His favorite: “Where did you get those nice threads? You look like a million dollars.”

In his 26-year career as an FBI agent, the 6-foot-4 Garcia took part in undercover investigations in 24 of those years, and none of his targets — including the hundreds of suspects he helped put in jail — ever unmasked him. From Miami to New York, Atlantic City to Los Angeles, he pursued mobsters, drug traffickers, and corrupt politicians and cops. He participated in 45 long-term operations and many more short-term ones, more undercover cases than any agent in FBI history.

In many of his missions, Garcia posed as a mobster named “Jack Falcone,” in honor of the Italian judge Giovanni Falcone, killed by the Sicilian Mafia in 1992. Although he is originally from Havana, Cuba, and moved to the Bronx at age 9, Garcia told his Mob marks of his Sicilian heritage. He had an expertise in stealing and fencing stolen merchandise — jewelry was his specialty. Sometimes, he had to run several undercover roles at once. He held several I.D. cards and took advantage of his fluency in Spanish and Italian to maintain his cover. However, he had to be careful not to mix things up when the phone rang.

In the early 2000s, the FBI tapped Garcia for what would be the most fruitful infiltration of an organized crime family since undercover FBI agent Joe Pistone’s operation in the 1970s. Disguised as “Jack Falcone” for two years with the Gambino’s chapter in Westchester County, New York, he flashed cash, Rolex watches, diamond rings, flat-screen TVs and other supposed stolen property (actually items seized in other FBI cases). This increased his popularity among the crime family members. Much of the cash he held went to pay for expensive dinners he paid for — mobsters, he said, are notoriously cheap when the check comes — to develop relations with his underworld marks. Consequently, he gained 80 pounds during the two-year operation.

One syndicate man he grew close to was Gambino capo Greg DePalma, a greedy individual drawn to Garcia’s access to money and hot property. DePalma would become his almost daily companion. The “old-school” hood was released in 2003 after languishing for 70 months in federal prison for racketeering. Almost immediately after his release, DePalma began threatening and extorting owners of Westchester-area construction firms, strip joints, restaurants and other businesses. Garcia said he witnessed DePalma commit a crime almost every day.

Garcia posed as a Mob associate looking to invest in a topless bar in the Bronx, owned by an FBI informant. Garcia’s inquiries led to a meeting with DePalma in 2003. By providing stolen property for DePalma to sell for cash, Garcia convinced him that “Jack Falcone” was an experienced jewelry thief and fencer from Miami. While hanging out with DePalma over the next two years, Garcia wore a body wire. Meanwhile, the FBI planted surveillance bugs at DePalma’s hangouts, even the hospital room where DePalma’s son, Craig, lay comatose after a failed suicide attempt. Garcia gave DePalma a complementary cell phone that the talkative Mob capo used prodigiously and naïvely, not knowing the FBI was listening.

The operation yielded 5,000 hours of recorded conversations used to implicate DePalma and other Gambino members on federal racketeering charges. In 2005, DePalma planned to honor “Falcone” by making him a “made” man with the Gambinos. In a recorded conversation later used as evidence in court, Garcia replied to DePalma, “I’m honored for that. I will never let you down either.” Garcia and Pistone are the only law enforcement officers who were nominated to be “made” in the Mob.

But being made was not to be, of course. After Garcia witnessed a Gambino soldier beat another family member with a crystal candlestick at a department store, the FBI shut down the 28-month undercover investigation.

Garcia’s efforts inside the Gambino crew paid off big time. The evidence he delivered for the FBI resulted in the arrest of 32 Gambino members and associates, including DePalma, family boss Arnold “Zeke” Squitieri and underboss Anthony “The Genius” Megale.

DePalma went to trial in 2006. Garcia, who retired from the FBI two months before the trial began, agreed to testify in federal court in Manhattan. In the end, the jury found DePalma guilty on more than two dozen counts related to racketeering and extortion. A judge gave the 74-year-old a prison term of 12 years and seven months. He died in prison at age 77 in 2009.

Among Garcia’s many undercover cases for the FBI, one stood out as personally upsetting to him. The mission was to detect possible corruption within the police department in Hollywood, Florida. For three years, Garcia impersonated a captain in the Gambino family. He discovered that some of Hollywood’s officers simply allowed crimes to occur. In one situation, he observed cops standing guard over the transfers of large amounts of heroin to traffickers. The FBI captured city police on video distributing what officers believed were stolen diamonds and artwork. Garcia’s ruse as a mobster ended with arrests, guilty pleas and prison terms for two sergeants, a detective and an officer.

“What was amazing to me,” Garcia later wrote in his 2008 book on his undercover years, Making Jack Falcone: An Undercover FBI Agent Takes Down a Mafia Family, “is that it was so easy to get cops to look the other way, to guard trucks for us, no questions asked. I’ve never seen anything like it.”