To join the Cosa Nostra you need to be of Italian descent - to talk the talk, walk the walk, and know your way around a menu. That didn't stop undercover FBI agent Jack Garcia. With little more than his wits, a wire, and an encyclopedic knowledge of Italian food, Jack infiltrated New York's notorious Gambino crime family.
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True Spies Episode 57: Making Jack Falcone

Disclaimer: This episode contains graphic descriptions of violence, and contains references to suicide.

NARRATOR: Welcome to True Spies. Week by week, mission by mission, you’ll hear the true stories behind the world’s greatest espionage operations. You’ll meet the people who navigate this secret world. What do they know? What are their skills? And what would you do in their position?

This is True Spies Episode 57: Making Jack Falcone.

JACK GARCIA: I mean, he was just beating on this guy, and then he goes to really hit him. And I said: “Let's get out of here…”

NARRATOR: Let’s begin at Bloomingdale's. Big department store, New York City. Nice, if you can afford it. Jack Falcone, an associate of the Gambino crime family, looms over the groaning figure of Petey ‘Chops’ Vicini. Petey has felt better. Falcone’s big hand rests on the shoulder of Robert Vaccaro. Vaccaro, wild-eyed and panting, holds an ornate metal candlestick. It’s dripping a sickly, scarlet puddle onto the floor of the homeware department. A fourth man - older than the others - begins to walk away. That’s Greg DePalma.

JACK GARCIA: As we're walking down the escalator, the guy gets up. Vicini, he's bleeding through the head profusely. He goes: “What did you do that for?” Greg goes: “You know exactly why I did that. And you better show your ass in front of that nursing home tomorrow. You understand? Or we're going to come back.” 

NARRATOR: He means it, too. Gambino, Bonanno, Colombo, Genovese. Lucchese. Five names. Five families. One mob.

JACK GARCIA: Yes. The FBI has had tremendous success on organized crime. But the organized crime, Cosa Nostra, is still here. And every time you hear of one of these takedowns by the FBI: “Oh, the organized crime is done. Cosa Nostra is done.” No, it isn't.

NARRATOR: Cosa Nostra - ‘Our Thing’ in Italian - is the name that most mobsters prefer. After all, anyone can belong to a mob. Where’s the exclusivity? No, to be a member of the Cosa Nostra, you need to be of Italian descent. You need to walk the walk, talk the talk, and know your way around a menu. The Cosa Nostra is built on decades of rituals, hierarchies, and intricate codes of conduct - which is to say, that for an undercover operative, they’re a hard nut to crack. Hard, but not impossible.

JACK GARCIA: Hi, my name is Joaquin ‘Jack’ Garcia, I'm a retired special agent of the FBI. I was working undercover for the FBI for 24 out of my 26 years of service. During my undercover days at the FBI, it culminated with my infiltration into the Gambino crime family in New York. I was proposed for membership by Captain Greg DePalma.

NARRATOR: By his own admission, Jack Garcia does not look like an FBI agent. 

JACK GARCIA: I looked like just a typical tough kid from the New York area, as opposed to some of the FBI agents that [look like they’re] from the Midwest.

NARRATOR: Standing at a burly 6'4", he certainly makes an impression.

JACK GARCIA: And I just had the dark hair, the swarthy complexion. And of course, the way of walking and talking.

NARRATOR And yes, to the untrained ear, Jack’s the quintessential New Yorker. But his story begins a little further south.

JACK GARCIA: I was born in 1952 in a prominent family in Cuba and life was very good for us. And then in 1953, Fidel Castro came to power.

NARRATOR: Jack’s father was an employee of the Batista regime - the US-backed government that was overthrown by Castro in the Cuban Revolution. In 1960, the senior Mr Garcia was forced to flee the country, after being accused of corruption by the new regime.

JACK GARCIA: He fled under cover of darkness. We were forced to move to my grandparent’s home. And then we got together and he brought us over to America. So I lived under communism for three years. And I tell you, it was one of the most brutal times of my life. And then when we came to America. We came to live in Washington Heights, New York. And then, later on, moved to the Bronx, New York.

NARRATOR: Like many Cuban refugees of his generation, Jack loves his adopted country fiercely. But his decision to serve it as an FBI agent was influenced less by patriotism, more by Al Pacino.

JACK GARCIA: Well, when I was in college, I used to play American football, I guess because of my size and stature. We used to go - before the games - to movie theaters to watch movies. We went to see a movie called Serpico. Serpico is with Al Pacino, and it's a story about this police officer who uncovers corruption in the NYPD, while all along going to work undercover. So when I watched this movie, I really felt I was touched and I said: “This is what I want to be. I want to be a police officer. I want to work undercover.”

NARRATOR: Shortly after graduation, Jack filled in an application for the FBI. And then he waited. And waited.

JACK GARCIA: So, of course, I didn't hear from the FBI for a couple... like a year. I wasn't even getting correspondence. And then I was home watching Univision and I was watching this Spanish-speaking show. And there was an FBI agent - who was non-native - butchering the Spanish language, asking for Spanish speakers to come and apply for the FBI. So I immediately got on the phone the next day, called, and said: “Hey, you have my application in the FBI. How come you are looking for others? I'm your man. Don't look any further.”

NARRATOR: Unfortunately, the same circumstances that had given him a native command of Spanish were working against his application.

JACK GARCIA: And they said: “Well, reviewing your file, we see that you're not even an American citizen.” So I had to become an American citizen in 1976 in order for them to process my application, which I did. And then finally in 1980, I became a special agent of the FBI.

NARRATOR: At first, Jack wanted nothing more than to fit in with his new colleagues.

JACK GARCIA: Well, when I got to the FBI, Quantico, Virginia, I no longer wanted to be an undercover. I was happy being a G-man. I mean, I went out and bought a three-piece suit. I bought those wingtip shoes - they're called ‘Thousand Eyes’ - and I just wanted to work bank robberies, fugitives, all of this stuff that at that time the FBI was known for.

NARRATOR: He may have set aside his undercover ambitions. But they weren’t done with him. On one of Jack’s early operations with the FBI, his team was tasked with hunting down a dangerous fugitive, a murderer. Their sources had revealed that the fugitive frequented massage parlors in Manhattan. A number of agents had already attempted to infiltrate these parlors without success - they looked too much like cops. Now, new intelligence revealed that one masseuse, in particular, had become one of their target’s firm favorites. The FBI couldn’t afford to lose this lead too. They needed a fresh approach.

JACK GARCIA: So, who else but this Cuban kid from the Bronx would fit the bill to go into a massage parlor as opposed to these other guys that look just like typical FBI agents and G-men? So, I went into this massage parlor. I, of course, put on my tennis sneakers. I went in there in a T-shirt: “Hey. How you doing? I'm looking for so-and-so.”

NARRATOR: It quickly became clear that none of the parlor’s employees had any misgivings about Jack.

JACK GARCIA: And I was told: “Well... Go in that room and get naked.”

NARRATOR: You’re a rookie FBI agent on your first undercover operation. You’ve been hoping against hope that you’ll keep your nerve, but never mind that - are you going to keep your trousers?

JACK GARCIA: So here I am into this uncomfortable situation. I'm down to my civvy shorts. And next thing you know, they walk in and I said: “Look, I'm looking for her. I owe her some money.” And then: “Well, how about me, baby?” I said: “No, babe. Look, I'm looking for her. This is the person I need to talk to. Where can I find her?”

NARRATOR: A good undercover agent needs to be adaptable. Very few things are worth blowing your cover for, and modesty isn’t one of them.

JACK GARCIA: You have to be able to fit in the environment that you are placed in and you have to, more important, be comfortable in that environment.

NARRATOR: Yes, Jack had committed fully to his role. And it paid off.

JACK GARCIA: She said: “Well, she's working at such-and-such a place.” So. I quickly got dressed, walked out. We had the address. Boom.

NARRATOR: Eventually, the FBI caught their fugitive. And Jack had caught something else, the undercover bug.

JACK GARCIA: So after I did that, did I feel good? Yes. I felt - because, obviously, they were pleased with the fact that I was able to garner that information that they were looking for - that missing piece. But what happened was, is when the FBI in the early ‘80s started working narcotics along with the DEA, that's where I really blossomed, I guess, so to speak. Here I am. I'm a fluent Spanish speaker. I'm a guy from New York City. I'm a street kid. You know, I grew up in Washington Heights. I grew up in the Bronx. So now we're working narcotics. So who else would they utilize? So I started working undercover.

NARRATOR: In the years that followed, Jack became one of the FBI’s go-to agents on the narcotics beat. His Cuban background gave him a level of credibility that few of his colleagues could match in the field.

JACK GARCIA: So we were doing buy-bust cases. We were doing cases involving major drug cartels from Colombia. And, of course, later on, we dealt with Mexican cartels. So, that became my specialty. I became an undercover. But I worked solely undercover, which is also a very rare thing to have in the FBI, where usually people may work undercover here and there. I had no cases but solely undercover cases. I was working in Miami. I was working in Atlantic City. I was working in New York and New Jersey. So I was pretty much - Philadelphia - all over specializing in undercover. And, after a while, I got very good at my trade.

NARRATOR: So good, in fact, that he often worked those cases simultaneously, balancing multiple identities all over the country. Sounds confusing, no? The devil is in the details. Surely you’d slip up from time to time?

JACK GARCIA: Now, how was I able to do that? Well, it's kind of easy because each case you work, you're playing a bad guy, somebody, you know, like a bad drug dealer. So people don't ask those kinds of questions. They don't say: “Hey, tell me your legend. Tell me, when were you born? Where were you born?” You know, some of these people don't even have names they give out. It's... They use codes, like if I'm dealing with a drug dealer, his name is Lucho. That's all you got is Lucho. I can't go to Lucho and say: “Lucho, can you give me your full name and your date of birth?” Just like they would never say that to me. That smells.

NARRATOR: But, toward the end of his career, Jack would take on a case that required more meticulous attention to detail.

JACK GARCIA: Right back, probably a couple of years before I retired, three or four years, I got a phone call from an agent that I respect very much. So he says to me, he goes: “Jack, I got a great case for you.”

NARRATOR: An enterprising businessman from the Bronx had come to the FBI with a problem. He ran a strip club and he was being extorted for thousands of dollars by the Albanian Mafia.

JACK GARCIA: They were beating up customers. They were robbing from the place. They were breaking things. They were threatening people. And they went up to the owner and said: “Listen, if you don't pay us, we're going to keep coming back until you pay us. Okay? Because now, we're going to put our flag in here. This is our place.” So the owner goes: “What, are you crazy?”

NARRATOR: The owner was right to question the Albanian’s sanity. The club had once been operated by a captain in the Gambino crime family. This was Cosa Nostra territory.

JACK GARCIA: But that was years ago. And that guy was in jail at the time. So the guys, the Albanians came back, started beating up some more people. Finally, they said: “Okay, these guys are demanding $5,000.”

NARRATOR: The FBI had begun an investigation, hoping to lock up a few low-level Albanian enforcers. 

JACK GARCIA: And the very next day, a mob guy walks in all dressed up in his Brioni suit, alligator shoes, and he says: “Hey, I heard you had a problem with the Albanians. Well, I can make that problem go away.”

NARRATOR: Italian suit, expensive loafers, implied violence? You know who this is.

JACK GARCIA: Well, the FBI said: “Well, wait a minute. This is interesting. Who is this guy?” Number one, because they didn't even know who he was, but they knew after he came in that he was affiliated with the Gambino crime family. So they're saying: “This guy looks like they're doing your textbook extortion. They're creating a situation and they're offering a solution.” That solution was going to be: “Pay the mob guy and the Albanians will go away.”

NARRATOR: It’s around 2003, and the Albanian mob is an up-and-coming force in New York’s criminal underworld. They’re occasionally hired as muscle by more established groups - a useful buffer between law enforcement and their client. Now, the FBI knows who the brains behind the strip club shakedown really are. And they see an opportunity to infiltrate their organization. Soon, Jack would get to know the Gambino crime family intimately. But when he first took the call, he had his reservations.

JACK GARCIA: So I said to him: “Well, what exactly d’you want me to do?” [He] said: “What we want is a kind of a more mature, older, experienced agent. And you're going to have to pose as an Italian.” And I said: “Italian? I'm Cuban. What are you kidding me? I eat rice and beans and fried bananas. You want me to become…” So he goes: “Yeah, listen, I think you could do it.”

NARRATOR: Jack liked and respected this agent. His name was Nat Parisi, and he was of Italian-American descent himself. He would be the case agent on the Gambino operation, and if he believed that Jack was the man for the job, well, he probably was, wasn’t he? Besides, he’d always liked a challenge. Jack would be inserted into the situation, posing as the hapless strip club owner’s new business partner - a transplant from Miami with a taste for life’s less virtuous pursuits, looking to launder some drug money through the club. He would pay off the Gambino mobster and use that new friendship as leverage to gather intelligence on the rest of the organization. But the FBI had to move fast - any delays could mean more violence. Jack had to establish his legend, a fake background story, and it had to be convincing. And by his own admission, when he gets excited, Jack’s accent carries a distinctly Cuban twang.

JACK GARCIA: My role was that I came from Italian parents, but I was in Miami and I hung around with Cubans. So that's how we kept it straight.

NARRATOR: Okay, so you’re covered on that front. But if you want to rub shoulders with the Cosa Nostra, you need to be demonstrably Italian-American. Food, and the rituals around it, are a big part of that cultural identity. So, Jack was going to mob school and he was going to eat well doing it.

JACK GARCIA: So the agent, who is named Nat Parisi, says: “Well, look, I'll make you into an Italian.” I said: “All right.” So, we went over to Arthur Avenue in the Bronx, which is all Italian. And there we go. That's where I found my love of Italian food. We ate everything - you name it - but we were just eating food. This is what you look for in this. This is how you pronounce it, right? Because you had to get the right pronunciations, okay? You know, you can't claim to be Italian - or at least having been an Italian over the years - you can't say, like, 'Mozzarella'. If you say 'Mozzarella'... like, no good Italian calls it 'Mozzarella'. You know? You can’t make these mistakes.

NARRATOR: Once Jack was fully acquainted with the niceties of the Italian-American dinner table - as well as relative trivialities like credit cards, a social security number, and a driving license - he was almost ready to begin the operation.

JACK GARCIA: As tight as that was, I felt I needed more. So what I did is, one of the cases I was working in Miami, I decided to find a Mr and Mrs Falcone who had died. And finally, I found them at a cemetery in Miami and they became my parents who died. I believe it was in the ‘90s. Okay, now you ask: “Well, why is that necessary?” 

Let's suppose I’m with the wise guys down in Miami and we're having a good time. Maybe the guy doesn't trust me, or maybe the guy is being nice and he says: “Hey, Jackie boy,” he says, “I know you're from the Miami area.” Because that was the role I was playing. He says: “I know your parents died. Hey, listen, let's go to your parents’ grave. Let's put some flowers in there and pay our respects.” What are you going to do? And I would only hope that the real Falcone's family wasn't showing up at the same time I was showing up.

NARRATOR: Now that’s commitment. So, exit Jack Garcia. Enter, Jack Falcone - big, boisterous, and crooked as hell.

JACK GARCIA: So, I came in the next day and I paid the Gambino guys the $5,000 and the Albanians never came back. And then what happened is we hitched our wagon to this mobster. His name was Louis Filippelli, who is now a captain in the Gambino crime family. And we were trying to get to know him and infiltrate that group as well as the Albanian group.

NARRATOR: Jack could have done business with Louis Filippelli but, soon enough, a different opportunity presented itself. His name was Greg DePalma, a capo, or captain, in the Gambino crime family. He’d just been released from prison, and before he’d gone away the strip club had been under his jurisdiction.

JACK GARCIA: And right out of jail, he goes right to the club and claims the club back and said: “This is my club.” So Louis Filippelli comes back a couple of days later and says: “You have two options. You can go with Greg DePalma, who is a captain with us, or you could stay with me.”

NARRATOR: Well, better the devil you know, right? You know Filippelli. Greg DePalma? Not so much. But DePalma had certain attributes that made him an attractive proposition for the FBI - his big mouth, mainly.

JACK GARCIA: We chose to stay with Greg DePalma because Greg DePalma loved to talk. And we in the FBI love to listen… You wanted a guy to tell you what was going on. So we hitched our wagon to Greg.

NARRATOR: More to the point, Greg DePalma had been a big cheese before his stint behind bars.

JACK GARCIA: A lot of people forget Greg DePalma, at one time, owned the Westchester Premier Theater in the ‘70s, the late ‘70s, even before I met him. And he was a celebrity in New York circles. Why? Because Westchester Premier, besides Las Vegas, were the only two places in America where you could see Dean Martin. You could see Frank Sinatra, Sammy Davis, Sonny and Cher, Bette Midler, Dinah Shore, Dionne Warwick - and every Who's Who played at the Westchester Premier Theater - which, in reality, played for the Gambino crime family.

NARRATOR: At the time Jack met him, Greg DePalma, one-time man-about-town, was much diminished. Now in his 70s, he’d claimed to suffer from severe ill health during his time in prison. But appearances can be deceiving. Beneath his frail exterior, Greg DePalma hid a core of steel. Need proof? Here’s Jack with a touching DePalma family anecdote.

JACK GARCIA: Greg DePalma's son, his name was Craig. Craig was a made member of the Gambino crime family who was proposed by John Gotti Sr, and he was in John Gotti Jr's crew. And what happened was… when Greg DePalma went to jail, so did his son and John Gotti Jr for shaking down a strip club in New York called Scores. So, what happened was, as they arrested Craig DePalma, the son cooperated - testifies with the grand jury. Now, word gets all around town that he had cooperated. So what Greg DePalma did, he set up a meeting between his son and him in prison through the help of some - I guess - corrupt guards. And they sat down and said: “Now you're a disgrace not only to the Gambino crime family, but to our family, the DePalma family.”

NARRATOR: The next day, Craig DePalma was found hanged in his cell. He survived, but fell into a coma from which he would never emerge.

JACK GARCIA: Okay, so what happened is, he asked for a compassionate release of his son. His son is going to come out, so he puts him in a nursing home with the promise to the nursing director that there will be no mob activity because Greg DePalma was a celebrity gangster. They knew him from the Westchester Premier. He gave them his word. His son is released. He goes into the nursing home.

NARRATOR: What do you think happened next?

JACK GARCIA: The very first day because I was there, all the mobsters just start showing up and meeting at the nursing home. So that is where most of our meetings were.

NARRATOR: So, Greg DePalma was the kind of person who’d hold a business meeting over the comatose body of his son, under the assumption that the FBI wouldn’t wire the room on ethical grounds. He was right, too. Smart.

JACK GARCIA: The FBI did not wire the room. I mean, this man was, you know, the devil incarnate. And he was all about making money, shaking down people. And just he was loyal to the Gambino crime family.

NARRATOR: This was the man that Jack would have to befriend if he was going to make any headway in infiltrating the Gambinos. And before long, he’d have his opportunity. The newly-minted Jack Falcone had already impressed his new contacts in the Gambino crime family and was becoming a familiar face at the dinner table. On March 4, 2003 - just six days after DePalma’s release from prison - he’d be dining with the devil himself. That night’s venue was The Spaghetti Western - a regular hangout for Gambino affiliates. Blinking through the restaurant’s smokey interior, Jack zeroed in on Greg DePalma.

JACK GARCIA: It's kind of like it's a seduction. You know, if you come on too strong, you spook them. It's like, what does this guy want? What the heck? What did he come from? I want him to come after me. I'm the prey. That's what I want. So what happened is we will go out to dinner. He will show up. I would show deference: “How you doing?” I kept my mouth shut. I mean, who am I to start talking at the beginning? And we slowly wound our way into the guy, hearing his stories and then he started getting a little warm with me, and fuzzy with me.

NARRATOR: So, you’re taking it slow. Watching, waiting for your moment. What does DePalma need? And how can you be the one to give it to him?

JACK GARCIA: And then, what happened was, I saw that this guy smoked a lot of cigarettes. And even though he had, like, half a lung, he would still smoke cigarettes, but he would rip the filter off and just smoke it raw.

NARRATOR: As DePalma hacked and coughed his way through yet another unfiltered cigarette, Jack began to put a plan together.

JACK GARCIA: He was complaining about the price of cigarettes, which are really outrageous. And I said: “Well, I can get you…” I didn't say it to him. I said it to his driver. “Hey, look, I can get you some cigarettes from Jersey, from some guys that I know. And they are counterfeit, but they look identical to the real thing. And I can get them at such a price that... Hey, you make a little money on that, that's fine, too.”

NARRATOR: A nobody like Jack Falcone wouldn’t make his approach directly to a big shot like DePalma. The driver offered a respectful buffer between the old man and his undercover suitor.

JACK GARCIA: So that all of a sudden tweaked the driver, who in turn talked to Greg DePalma, and now he was interested. So I took cases of cigarettes from another case that I was working in Atlantic City with Asian organized crime, and we just simply gave them to Greg DePalma for this really cheap price.

NARRATOR: Yes, one of the benefits of working several undercover jobs at the same time is that you have access to a lot of seized contraband.

JACK GARCIA: Now, it turned out for us that it was a good thing because three days later the driver said: “We couldn't unload these cigarettes. They were bad quality.” I said: “No problem, give them back to me. I got a way of unloading them. Now, don't worry about it.” And then I said: “Why don't we give them a tribute payment? Let me give him a $1,000 as tribute and say I made the score, I sold them. Here's your little taste for that.”

NARRATOR: So, as of now, what does Greg DePalma know about Jack Falcone?: 1) he’s got easy access to money, and lots of it: 2) he’s respectful - at least by mob standards and; 3) he’s got contacts - a network with whom he can buy, sell and acquire valuable goods. This was someone with whom Greg DePalma could be very good friends indeed.

JACK GARCIA: So one day the old man said - this is early on when I'm schmoozing him, like I'm courting him and he's courting me - he says to me: “Jackie boy, we're going for a ride.” Now, when you hear a mobster guy say: “You're going for a ride,” you know, you get a little tensed up, you know, like: “What do you mean?”

NARRATOR: What does he mean? Things have been going well, so far. But you’ve read the books. You’ve seen the movies. An impromptu drive with a man like DePalma so rarely ends well. Have you been discovered?

JACK GARCIA: So next thing you know, we land at a jewelry store. So he says to me: “Hey Jackie boy, just want to let you know we checked you out. And just to say you're a good man. You did the right thing with the cigarettes and all that. I want to give you a gift.” He gave me a ring, which is the gaudiest ring I've ever seen in my life. It was this big pinkie ring with diamonds all around. But they look like cheap diamonds or whatever it was. He gave me that. He goes: “You on record with any family?” I says: “No, I'm not on a record.” He says: “Okay, now I put you on record with us.” He says: “Nobody could mess with you. You are now one of us.” He says: “You need anything. I'm your skipper.” So I said: “Okay Greg, thank you very much.”

NARRATOR: With this tasteful demonstration of brotherly love, Jack became part of DePalma’s inner circle. In time, he even supplanted the old man’s driver, a position which gave the FBI unprecedented access to his movements.

JACK GARCIA: We knew in advance where he was going so we could set up the surveillance squad. We knew afterward what the meeting was about because I was recording him. I always wore a wire. I really felt that there is no better evidence than the voice from the defendant. I mean, to have to capture his voice on tape, he can't say my word against his. So all of my meetings, although dangerous as it is, I actually wore a wire. I believe in wearing a wire in all my undercover meetings.

NARRATOR: Those recorded meetings yielded information that helped to plug the gaps in the Bureau’s knowledge.

JACK GARCIA: We identified the hierarchy of the Gambino crime family. We also identified how many crews they had, who was getting straightened out.

NARRATOR: ‘Straightened out’ - another entry for your Cosa Nostra lexicon. You might be more familiar with the term ‘made man’. To be ‘straightened out’ is to be ‘made’. Once you’re ‘made’, you’re officially part of the mafia. You’ve taken the vow of omerta - silence - and now you can rise through the ranks. Soldier, Capo, Underboss, Boss. Of course, that’s if you live long enough. And if an FBI agent were to become a made man, well… they’d have the kind of access that most law enforcement agencies could only dream about. But for a mere associate to be ‘made’… well, they’d need to prove themselves worthy.

JACK GARCIA: Yeah, the first time I got asked to, I guess, test my loyalty, was to take somebody out by breaking his kneecaps with a baseball bat. It was a guy who was at one time a radio personality in New York, and he was avoiding Greg DePalma because Greg DePalma wanted to shake him down on something else. So, what happened, is he said to me: “Jackie boy, you see this guy? I want you to baseball bat him.”

NARRATOR: Now, obviously, FBI agents can’t go around shattering kneecaps. But beyond his moral qualms, there was another reason that Jack could not interact with DePalma’s unfortunate target.

JACK GARCIA: I knew the guy and he knew that I was an FBI agent because he played football the same place I played football - American football - so the last thing I want to do is go to him and say: “Hey, by the way, Greg wants to break your kneecaps.” And then how do I really trust him? Did I trust him enough? Maybe he’d go back and tell somebody.

NARRATOR: It’s a sticky situation. How do you keep Greg happy while avoiding contact with the mark? It turned out that sometimes, if you put something off long enough, it just sort of goes away.

JACK GARCIA: So I just kind of said: “Hey, Greg, I missed them. Oh, I just saw the guy was running lights and everything to get them. There was a cop and he went, so that kept him busy.” And then, of course, you know... that was it.

NARRATOR: Nicely done. The FBI needs to keep its hands clean. This is already a dangerous operation. You don’t want to give your superiors cause to pull you off the case, especially considering the kind of priceless intelligence you’ve been able to acquire.

JACK GARCIA: They didn't know at that time what the administration of the Gambino crime family or the other families were. So we were able to say the acting boss was Arnold Squitieri, underboss Tony Magali and Joseph 'Jo Jo' Corozzo. We were able to determine that. We also listed so many other made men that no one had any knowledge that they were guys who had been indoctrinated into the family.

NARRATOR: Jack was able to uncover the true extent of the Cosa Nostra’s network in New York. Construction, hospitality, even trade unions - the Gambino crime family had grown on the city like a tumor, corrupting the tissue of civic life.

JACK GARCIA: In fact, I was put in a union in order to get benefits, which they all need. I was put in Local 305. I went to this sit down with a bunch of mobsters and Greg DePalma and the president of the union. And I was put in a union where I had life insurance, medical insurance, dental, optics. I had better insurance than the FBI. And I wasn't even part of Local 305. I just paid my dues and I got all of these things.

NARRATOR: Soon, Jack was added to a list of potential ‘made men’ - replacements for any soldiers who died in the course of their nefarious duties.

JACK GARCIA: And what that is, is a list has circulated among the family and it has the name of the person being proposed next to the guy who has died.

NARRATOR: This would have been an important moment for any aspiring mobster. For an aspiring mobster who also happened to be a Cuban-American FBI agent, it was almost unthinkably fortunate. As a made man in the Gambino family, Jack would have unprecedented access to New York’s criminal underworld.

JACK GARCIA: And then, what would that mean is, that now I would be an Amico Nostro. That, in Italian, means I would be a goodfella, I would be a wise guy. And that means that I now have protection of the family, even though I have it as an associate. I really now have it. This is on a different level altogether.

NARRATOR: As Greg DePalma’s power and influence continued to recover, he began to grow his personal crew. One new arrival stands out in Jack’s memory. His name was Robert Vaccaro.

JACK GARCIA: Robert's the kind of guy who really was true Cosa Nostra. He didn't put his business out there. He was very discreet. He was also... had those killer eyes. I mean, you could look into his eyes, you see his soul. There was something dark in him.

NARRATOR: Unlike Jack, Vaccaro was a made man. He’d been brought on board to be DePalma’s acting Capo, an extension of his power in the city, a proxy. After all, DePalma was still on parole. He couldn’t be too visible. Suffice to say, Jack had his misgivings about Robert Vaccaro.

JACK GARCIA: I was a little concerned because I said: “Was Robert put in here in order to whack Greg because of his son’s being an informant? Was he marked for death?”

NARRATOR: Ultimately, this was not the case. But you can never be too careful. And while he was loyal to DePalma, Vaccaro was somebody that you absolutely needed to be careful around. In 2004, Petey Chops, a low-level Gambino soldier, would find that out for himself.

JACK GARCIA: His real name is Petey ‘Chops’ Vicini. So the problem with Petey Chops was that he was not showing up. And part of being in the mob and operating under the umbrella of the mob is that you have to kick money up. Money always flows up in the mob, never flows down. And if you're making money, then your captain needs to be making money. And the boss and the consigliere need to be making money.

NARRATOR: Petey ‘Chops’ Vicini was not paying his dues to Greg DePalma, and the old man wanted to know why. If he was going to find out, he’d likely need some muscle behind him.

JACK GARCIA: So he calls me up one day, says: “I need you to come with me here.” So I show up at the restaurant. Robert is there. He says: “We got to go. Get in the car. We're going for a ride.” Right. We go for a ride. “Well,” I said, “Greg, where are we going?” And he goes: “We're going to Bloomingdale's.”

NARRATOR: Bloomingdale's is an upscale department store in Manhattan. As they drove, Greg explained that Petey Chops was a regular visitor.

JACK GARCIA: So I said: “Well, how do you know this? He's going to be there?” Says: “I put the feelers out there. They told me he shows up every fakakta day of the week. He shows up like clockwork. He brings his goomar there, his girlfriend, and then he goes and hangs out at the little cafeteria while she goes and spends his money, you know?”

NARRATOR: The menacing trio - DePalma, Vaccaro, and Falcone - arrived at the Bloomingdale's cafeteria. They looked around. No sign of Petey Chops. Jack breathed a sigh of relief. Maybe, as it had with the would-be kneecapping victim, DePalma’s ire would fade as he lost interest in the chase.

JACK GARCIA: So he said: “Usually he's here.” So we finally gave up and said: “Ah, we'll try next week.”

NARRATOR: You didn’t think it’d be that easy, did you?

JACK GARCIA: And just as we're walking out, here comes Petey Chops and two women. Now, Petey Chops sees us. And I'm telling you, if time could stop, his eyes just lit up like you wouldn't believe. I mean, he says to the girls: “Girls go shopping, you know?” So he goes: “Greg, what are you doing here?” He goes: “What am I doing here? Where you been? So you're supposed to be coming to see me and you're supposed to be kicking up.” “Oh, you don't understand. I'm being followed,” he says. “We're all being followed!”

NARRATOR: If only he knew.

JACK GARCIA: So Greg goes: “Listen, you better show up here tomorrow.” And the guy started getting attitudinal with Greg. So Robert and I walk over, and he starts getting snarky with Robert. And right away, the eyes kicked in. You know, I said: “Oh, this don't look good.” He goes: “Who am I?” He grabs a Kosta Boda - never forget this - a Kosta Boda candlestick holder that kind of resembles a weight, a 25 lb weight, not only in the way it looks, but also the way it feels. He grabs this and he goes: “Who am I?” Cracks him over the top of the head. You hear a pop like a melon and then blood starts gushing out. This guy drops right down at bottom and then you hear the yelling: “You f*** this…” I've never heard the F-word used in so many colorful ways.

NARRATOR: Okay, freeze. You’re an undercover FBI agent and you’ve just witnessed a brutal physical assault. Do you step in? Put your cover at risk? Assess the situation? How far can you let this go?

JACK GARCIA: I mean, he was just beating on this guy and then he goes to really hit him. And I said: “Let's get out of here. Come on, Robert, what are you doing? The cops here, we're on camera.” So he drops the Kosta Boda down. He's done. As we're walking down the escalator, the guy gets up. Vicini, he's bleeding through the head profusely. He goes: “What did you do that for?” Greg goes: “You know exactly why I did that. And you better show your ass in front of that nursing home tomorrow, you understand? Or we're going to come back.”

NARRATOR: Time to make a hasty exit. If you get picked up by law enforcement, it could look suspicious if you’re released early.

JACK GARCIA: Meanwhile, my brand-new leather coat is totally soaked in blood. Right? We're going down the escalator. You see these cops running up. And Greg DePalma never missed a beat, says: “Some guy just fell off the escalator. He's upstairs crying like a little bitch.”

NARRATOR: When Jack could be sure that it was safe to do so, he called in a report to the FBI.

JACK GARCIA: They go over to the place, gather the evidence, the film, and all of that, talk to the people. And they were saying how this giant guy was there and this other guy kept beating them. And it was just horrendous.

NARRATOR: Jack had been privy to the kind of brutal violence that underwrites the Cosa Nostra’s power. We can safely assume that Greg DePalma trusted him implicitly. He could, feasibly, have gone all the way to the top.

JACK GARCIA: You know, we were making so much great progress in this. We were moving forward to get straightened out. But there was one meeting that I had with Greg DePalma and Robert Vaccaro at the end. He says: “Jack, Jackie boy, we're going to have to put you on hold.”

NARRATOR: It was just DePalma, Jack, and Vaccaro. On the surface, all was calm. Underneath, Jack was starting to sweat.

JACK GARCIA: And I go: “Well, what's going on?” He says: “We got information that somebody big is cooperating and somebody flipped. So everything is on ice right now.”

NARRATOR: Did they know? Vaccaro’s vicious beating of Petey Chops was still fresh in Jack’s memory. They wouldn’t kill law enforcement if they discovered him, but he’d be unlikely to leave unscathed. Fortunately, there was more than one mole inside the Cosa Nostra.

JACK GARCIA: And that turned out to be that someone was Joe Massino, who was the boss of the Bonanno family, who did indeed cooperate.

NARRATOR: Jack had dodged that particular bullet. But unfortunately for him, Greg DePalma did not hold a monopoly on caution.

JACK GARCIA: Then what happened is, within the next week or two, the FBI management says: “Well, we're going to end the case.” And I said: “You've got to be kidding me,” I said, “We've seen it this far. We are going to get straightened out to give us access to that inner sanctum, to really find out what's going on in that world.”

NARRATOR: Jack fought the decision. There was no threat to his life, he argued. And he was getting closer and closer to being a fully paid-up member of the mob. On the FBI’s organized crime team, that’s the holy grail of intelligence gathering. Only one agent had ever come this close before - Joe Pistone, the inspiration for the Hollywood blockbuster Donnie Brasco.

JACK GARCIA: He was out there for six years. I'm out there less than three years and I'm being proposed. So why don't you give me as much time as you gave Joe?

NARRATOR: Now, it seemed that Jack would be denied his own movie moment. The case was shut down.

JACK GARCIA: And the decision was made. We took down 32 members and associates. We took down the administration, which was the boss, the underboss.

NARRATOR: So, not a complete loss. But it could have been so much bigger.

JACK GARCIA: Some of the excuses I heard is that they felt that this case was so large, and which now would require maybe the involvement of more agents or police, and they couldn't handle that. That was such, like, a hot rock for them, that the management maybe they felt they were going to lose control. But, hey, you know what? They didn't lose any control when they stood there on the podium and tapped each other on the back of the great job they did.

NARRATOR: Now, Jack began preparing for his day in court. His ‘always on’ recording policy was about to pay off.

JACK GARCIA: It was decided by the majority - except for one person - to take a plea. Okay, they wanted to [do] what they call a global plea. That means everybody is... And this is usually ordered by the boss. Everybody takes a plea of guilty. So only one person said no. And that was the person that we had the most tapes on, and that was Greg DePalma.

NARRATOR: Greg DePalma would live to regret that decision.

JACK GARCIA: Greg DePalma comes out with, you know, somebody driving him in a little wheelchair. He had the oxygen mask. He had a little blanket on looking so feeble and so... meanwhile, just a couple of months ago, he was slapping some guy around. So he's sitting there and we're playing tape after tape after tape. And then the very last tape we played was when Greg was sentenced to prison on the Scores’ strip case where he went with John Gotti Jr and his son. He's saying how he fooled the prosecution to let them think that he was dying. They sentenced him to such a low sentence because they said this man would not be alive. And he talked about having a wheelchair, unshaven, drooling, and looked so feeble that they felt sorry for him and lowered it. Well, sure enough, this is being played and there's Greg DePalma duplicating the same thing. No more questions. I walk out as I walk by Greg DePalma. I hear him whisper from the below of his voice: “You cocksucker.” And I walk away. And, of course, it was just the way he said it. It was kind of classic because he had been caught. His game was over.

NARRATOR: Greg DePalma died in prison a few years later, in 2009. Robert Vaccaro was jailed for his violent assault on the shop floor of Bloomingdale's. Today, Jack’s happily retired. For a while, there were rumors that the Gambino crime family would seek retribution but he never bought that line.

JACK GARCIA: They said there was a contract for $250,000. Okay, so somebody else kills me. Are they going to walk into a social club and say: “Hey, I whacked Jack Falcone, give me my money?” It doesn't work that way.

NARRATOR: But he’s no fool, either.

JACK GARCIA: I don't go back to the restaurants that I used to love going to eat. I can't go back there. I don't go driving the same way. I'm always looking in my rearview mirror. I take precautions. But, hey, before they come after a law enforcement agent, there's a lot of informants out there who are in wide-open spaces, operating podcasts, TV shows, you name it. Why are they going to come for poor old Jackie Falcone? And if they come after me, they better be ready because I got the firepower. 

NARRATOR: I’m Vanessa Kirby. You can read about more of Jack Garcia’s undercover exploits in Making Jack Falcone, available in print, or as an ebook, now. Join us next week for another high-risk operation with True Spies

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DISCLAIMER: The views expressed in this podcast are those of the subject. These stories are told from their perspective, and their authenticity should be assessed on a case-by-case basis.

Guest Bio

Joaquin ‘Jack’ Garcia was a Cuban immigrant who lived in the Bronx and dreamed about working as an undercover FBI agent. His most difficult and deadly mission was also his greatest success; Garcia infiltrated New York’s Gambino crime family, adopting the persona of ‘Big Jack’ Falcone. He learned all about the organized crime syndicate - from loan-sharking to murder - but was Jack in too deep?

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