Frustrated with personal disappointments and career setbacks, a big dreamer in South Florida decides to pose as a member of an infamous mafia family, letting a genie out of the bottle that seems to give him everything he dreamed of, until complications threaten to turn him into the real thing.

On April 8, 2009, on an unusually chilly day in South Florida, Chris Gambino, 45, sat down to make the biggest deal of his life. The man with Chris had explained he represented a trustee of a pension fund for a major retail chain that was interested in buying a portion of Chris’ company, Messana Holdings. The lucrative arrangement was a turning point for Chris Gambino, the culmination of a life that commanded respect, confirmation that he was someone important people needed to deal with.

Chris had black hair graying at the temples, dark caterpillar eyebrows, and a face like actor Michael Imperioli’s with a mole on his right cheek. He talked in the gentle, Queens-accented voice of a wise guy, no surprise coming from a Gambino. In the 1950s, when Carlo Gambino headed one of New York’s infamous Five Families of the mafia, the name Gambino became synonymous with organized crime. Decades later, the Gambinos’ charismatic boss, John Gotti— nicknamed the Teflon Don—made the family a national fixture, with a sensational trial for murder and racketeering in 1992 becoming a staple of media coverage while leaving the crime family in disarray.

Chris lived in a large home in Boca Raton with his wife, a pixyish blond Romanian model, and he often arrived at appointments in a black limousine. Under the banner of Messana Holdings, he ran several businesses, including a fashion line called Gambino Apparel, whose signature item was a pair of jeans with bullet holes cut into them. “It’s a crime not to wear them,” read the tagline to a glossy black and white ad showing six women wearing only the jeans, covering their bare chest with their arms. Chris didn’t drink but he was often out on the town, appearing in photos with Evander Holyfield, Billy Baldwin, Dennis Rodman, and Mickey Rourke. He had become a big shot in South Florida, which helped lead him to the opportunity at hand.

This was no ordinary pension stock-buying deal, becoming more apparent as the meeting progressed. Chris’ new business associate needed money laundered. Chris explained what he could do for them. “I can handle up to $25 million [abroad],” he said. “If you wanted it washed here, we can do that, too.” If only they could see him now: the old guard mobsters he’d tell stories about, the ones who promised him he’d always be stuck on the streets of New York as the lowest Gambino errand boy. Now, he’d have an empire.

When the need for complex international logistics and connections were discussed, Chris reassured his new colleague. He wasn’t just getting a partner. He was getting an army.

“Listen, there’s 300 fucking soldiers in my family,” Chris said, bluntly explaining why he was the man to be at the helm. “You’re talking about the Gambino family.”

But there was a problem—the bigger issue than how to launder 25 million dollars.

Chris wasn’t a Gambino at all and never had been. In transforming his identity and himself, he had managed to get pretty much everything that had once eluded him. And the ruse was convincing, pulling in almost everyone around him. But that was also the rub. He was so convincing that glory-hunting investigators and desperate hangers-on multiplied, and now the walls were about to close in.

Christopher Horton was surrounded by garbage. The enormous trucks roared to and from the hub of the sanitation department for the city of Deerfield Beach, Florida, where he worked. Along with the ear-splitting noise of the vehicles came the rotting smells of refuse and the sights of the exhausted, underpaid employees like him.

Surveying the scene, Chris, as he approached his mid-twenties, had plenty to reflect on, a cycle of failure that haunted him wherever he went. A marriage began and ended, with squabbles still ongoing past the marriage’s sell-by date. While other people seemed to succeed despite themselves, often through sheer luck or connections, he scraped by. Construction. Catering. Now sanitation, a cliche of dead ends, other than maybe the mob wiseguys rumored to profit from it. In many ways, Deerfield was the perfect spot to wallow in regret and envy. To the north was luxurious Palm Beach, to the south was hip Miami, and Chris, as usual, seemed lost in limbo. Twentysomethings are prone to feel a jolt when life plans fall through. Chris always thought maybe he could do something special, maybe follow a childhood plan to be a first responder, maybe indulge his creative side.

In contrast to the doldrums of reality, flipping through the culture section of the Miami Herald or the Sun-Sentinel reflected a renaissance in mafia-related media that piggybacked on John Gotti’s downfall, which was exposing the mob’s inner workings on the nightly news. Two bestselling nonfiction books, Wiseguy: Life in a Mafia Family and Casino: Love and Honor in Las Vegas, both of which became Martin Scorsese movies (Wiseguy retitled Goodfellas), depicted cigar-filled back rooms of bars hosted twisted codes of honor among mobsters whom everyone kowtowed to. In Donnie Brasco: My Undercover Life in the Mafia, also destined to be a hit movie, even an FBI agent couldn’t resist the aura of being a wise guy.

Chris set himself a quest, a mission to be respected. Was that respect out there waiting to be grabbed, as simple as showing up with a new identity a la “Donnie Brasco,” the undercover agent’s brash alter ego? Like many South Florida transplants, Chris had roots in New York City. He decided to change his last name, which, on the one hand, was a rather mundane course of action that involved filling out and dropping off tedious forms with the court system. The big swing was filling out that form with the name Gambino. Why not? South Florida had long been a mecca for mobsters in hiding or in transition, back to the days when it was a “mafia Switzerland,” where organized crime families had an unspoken rule that they could not claim territories for themselves. Chris’ work in sanitation, with its reputation for being mob controlled, might give him credibility.

But could a name make a difference? It wouldn’t hurt to have a fresh start, particularly since an insurance company nagged him over claims on a disability policy. As his new name got out there, people seemed intrigued by Chris Gambino in a way they had never been by Chris Horton.

It was a new beginning, inspiring him to try his creative chops. He began writing a novel called My Only Son, the story of Vinny Denucci, who grows up siloed from his mafia boss father Sonny’s business. When he turns 21, Vinny is forced to abandon his law school plans to be his father’s successor, completing his “assigned birthday ritual” by killing a disloyal member. Now a “made man,” Vinny struggles with his conscience, wavering between a life of sin in the mafia and what he knew was moral.

Chris hired Marilyn Willison, a West Palm Beach-based writer and editor, to help him finish his book and prepare it for self-publication. “He didn’t know where to begin” when it came to organizing his thoughts, she recalls, but he seemed very proud of being a Gambino. Chris implied to her that he had gone to law school without graduating, beginning to conflate himself with his fictional character.

Chris included an author’s note that pointed to inside knowledge of mafia life without claiming it outright. “My Only Son is a novel about organized crime… As you will quickly determine, I am including realistic information which, as far as I am aware, has not been published before.” Writing My Only Son, he noted, helped him purge “painful memories.”

For a self-published book with its fair share of grammatical mistakes, My Only Son began to generate more interest in local media than anyone expected. Chris Gambino was emboldened and ready for more.

The attention his book received became a light bulb moment for Chris: Gambino was much more than a name. It could be a business, a way of life. An escape from the dead ends Chris had slammed against time and again. At one point, Chris was picking jeans off the floor of the room of his daughter, whom he shared with his ex-wife. He noticed holes in her jeans. If women liked Swiss cheese-jeans, why not take it to the next level? He brought a pair of jeans to a friend’s shooting range and used them as a target. After a few rounds of shooting up denim, he later recalled, he knew he had stumbled on “something hot.” Chris accessorized the bullet holes with Swarovski crystals and found a Brazilian manufacturer to make more of them. There was only one choice for what to call the brand: Gambino Apparel.

After putting out a call for models to use in his fledgling fashion brand, a European modeling agency connected Chris with Evelina, who had come from Romania. Energetic and peppy, Evelina saw the potential in Chris’ vision. She had her ideas for how the apparel line could be both sexy and classy. Beyond the fashion talk, the two hit it off. A whirlwind romance became a marriage. Together, they officially launched the apparel line at a hip nightclub and announced a series of promotions by Scarface and Breaking Bad actor Steven Bauer. At one point at Miami Fashion Week, a model wearing a fedora, necktie, suspenders, and bullet-riddled jeans stalked the catwalk in front of a hundred-odd people in the audience. She put her hands in the shape of a gun and pointed at the ceiling while pops of gunshots blasted from the speakers.

Chris saw no reason to stop with a clothing line. He developed Italian olive oil, music production, wines and spirits, and an energy drink called–what else?–Mobstar. He also unveiled a music label called Block Star Records, which released two songs called “Gambino” and “Gambino Status.”

In a few short years, Chris had gone from a frustrated divorcee with dwindling prospects to a rising entrepreneur with a Romanian model on his arm. “Nothing compares to the satisfaction of achieving that one goal in life which is to follow your dream,” he mused. He was invited to speaking engagements to discuss overcoming complex backgrounds and persevering. He wore a mustache and mullet and often dressed in a pinstriped suit. “From growing up, and what I’ve been taught and what I’ve seen, being involved in, let’s say, an organized family, you have two outcomes: death or jail,” he told one TV reporter. In a somewhat muddled message, he added that his goal was to let people know that “the grass isn’t greener on the other side.” Reading aloud to a semi-circle of elementary schoolchildren in the decidedly non-mean streets of Boca Raton, he stopped to relish a line about fruit trees: “Some of the buds develop into sweet-smelling apple blossoms.” Yet another idea was added to his to-do list: writing children’s books.

Similar to other mafia personas like Henry Hill (immortalized in Goodfellas), it was never clear if Chris was in or out of “the life,” which added to the fascination with him. On the social scene, Chris became a mainstay at hot spots. He could be spotted dressed in all black, with gold rings and a chain dangling from his neck with a pendant that read “My Only Son.” He boasted an entourage that included an imposing bodyguard, Brian. They would wear Gambino Apparel shirts reading “Made Man.” A reporter, Deirdra Funcheon, saw this up close when she was assigned to profile Chris for the Miami New Times, while WFBF, a West Palm Beach affiliate, followed him with cameras to some of his appearances around town.

Coming full circle with the pop culture portrayals of powerful wise guys that had inspired him, Chris’ novel eventually found its way to a New Jersey movie producer named Suzanne DeLaurentis. DeLaurentis had done several low-budget, straight-to-video mobster flicks, including the mafia drama 10th & Wolf, starring Giovanni Ribisi, Dennis Hopper, and Tommy Lee. DeLaurentis’ company announced plans to turn My Only Son into a big-budget movie. They even gave Chris the go-ahead to write a script. He confidently predicted the film would earn millions.

Chris added acting and television commentary to his repertoire. According to his IMDB page, he appeared in shows including Magic City and Graceland and the news programs Hardcopy and Inside Edition “when his unique blend of insight and candid assessment are needed.” He became friends with Ken Wahl, the star of the CBS crime drama Wise Guy, and would often text Wahl’s wife, Shane Barbi—one of the famed Barbi twins—about her animal rights advocacy.

“From his humble beginnings in Queens, N.Y., ‘Mr. G,’ as he is known to his friends and associates, has lived a remarkable life, encompassing both difficult experiences and notable success,” his IMDB bio read. “An accomplished author and entrepreneur with an infamous last name.”

Meanwhile, Chris told people that epic mob drama The Sopranos, the latest TV sensation, had loosely based a character on him, also named Christopher and played by none other than Michael Imperioli, and he wasn’t thrilled about it.

Chris became so comfortable talking about being a Gambino he strayed from vague ambiguity, instead rattling off precise details. He would talk about his father, John Gambino, being shot and killed when he was 13, after which his uncles raised him. He would describe forming his own “crew” before serving five years in prison on a RICO (or racketeering) conviction after being betrayed by one of his trusted men. “Certain family members said, ‘you’re never going to amount to anything,’” he’d recall, “‘You’re going to be a street guy the rest of your life,’ and… I wanted to prove [otherwise] to myself.”

Deirdra, the New Times reporter, shadowed Chris for a while and found it challenging to keep his backstory straight or to make sense of his businesses. He invited her to a Gambino Apparel brick-and-mortar storefront in Deerfield Beach, in a strip mall next to a Domino’s Pizza. The smattering of sample clothes on racks didn’t suggest a venture that could support his lavish lifestyle, nor did it seem to be successful enough to expand into Jamaica and Tokyo, as he claimed. She also could not find any records of a RICO conviction for anyone named Christopher Gambino. He told her it was because he had paid $7,000 to have it expunged. For every question she had, the more Chris deflected.

With public scrutiny escalating, Chris spread himself thin with his countless enterprises, at one point being listed as the head of as many as four dozen companies, with Gambino Apparel, in part because of Evelina’s passionate and tireless work, remaining the most viable. When debts mounted, the companies would be restructured and renamed, often referencing the mob world (Gangstarwear, for example, and American Made Outlaw), with only a handful of them doing or making anything.

Even Chris’ beloved book, My Only Son, caused headaches. A local gym owner got into a dispute with an employee and sent him a photo of the cover of My Only Son, mentioning he knew Chris. The employee took it as a veiled threat, mainly since the book cover depicted a smoking gun, and aired the dispute publicly on a blog. Pat DeSimone, a plumber based in Palm Bay, Florida, who had become friendly with Chris in West Palm Beach, noted errors in the novel’s details about New York, where DeSimone grew up. Meanwhile, Marilyn Willison, the editor who worked with Chris to prepare the book, never received any payment.

Another novel about the mafia became a warning. Simon & Schuster gave a writer named Michael Gambino a $500,000 book deal and launched The Honored Society with fanfare. Thomas Gambino, the actual son of the famous mob boss Carlo, alerted the publisher that the writer was a fraud and not part of the family. It turned out the writer’s name was actually Michael Pellegrino, which resulted in books being pulled and the writer becoming entangled in lawsuits with the publisher.

Chris had deals–like that with the movie producer–that could fall through with any hint of the falsity in his biographical claims. And if the real Gambinos had paid attention to Pellegrino, would word also spread about Chris? Impersonating a law officer would lead to arrests by law enforcement; what could impersonating a wise guy call down on his head from the most powerful mafia clan in the country?

Chris had to stay one step ahead of every potential problem. Every flash of a smartphone camera along bustling South Beach could be aimed at him. Every dark sedan that slowed down on the street near him could be someone trying to keep an eye on him, or worse. Besides the invisible threats, he also needed to keep his known skeptics and creditors at bay. At one point, he engaged a Miami lawyer named Michael Rosen, who remarkably shared a name with the New York-based lawyer of the actual Gambino mafia family, a savvy choice by Chris that blurred the lines between him and the Gambinos.

As for Deirdra, who made her doubts clear to Chris through her questions, when he started to wrap up her profile for the New Times, she began receiving strange phone calls and emails. One caller claimed to be a reporter who worked at Vogue magazine, wanting to offer her a job.

“Deirdra, you don’t know me, but Christopher Gambino told me you are a really great reporter, and you should come work at Vogue,” the caller said. “Just don’t publish that story, just come work with us at Vogue.”

In the meantime, Chris had been so effective in promoting his mobster persona and his roots in the Gambino dynasty, shady characters naturally gravitated toward him. A company that had been involved in (failed) skin and sun care ventures acquired Gambino Apparel “through an exchange of shares of Common Stocks,” named Chris chairman and CEO, rescinded its acquisition deal with Chris, reorganized, changed its name to Patient Portal Technologies, Inc., and then acquired Patient Portal Connect, Inc., a healthcare admin and insurance reimbursement tech company. The head-spinning moves were the brainchild of two men who would create or acquire companies, pump them up to seem active, and fraudulently sell stock in them, all while using the shell companies as piggy banks. Chris’ endeavors were now squarely on the radar of federal authorities.

Brian, Chris’ “bodyguard,” who followed him around at nightclubs and driving ranges, was also busy with his schemes on the side. Brian got involved with two grifters cooking up a Ponzi scheme to defraud investment clubs made up of Haitian Americans living in Miami. Through an organization called HomePals Investment Club, this trio baselessly promised to double investors’ money every three months. Brian, who was not an attorney, posed as the company’s lawyer. Only 10% of the funds were used for trading, resulting in 20% losses, while the three men siphoned off $1.2 million for themselves. Brian earned a salary from HomePals of $8,000 per month and diverted $85,000 of investors’ money to pay for overdue child support obligations.

Inevitably, the HomePals Investment Club Ponzi scheme crashed, with authorities circling and major charges looming. Brian seemed to be out of luck, but he had an idea. He flipped on his partners and became a government informant, recording conversations and testifying against the other players. Still scrambling for the softest possible landing, he had another ace up his sleeve, a big fish he could hand over to authorities: a Gambino.

The excited expression on the faces of a roomful of FBI agents could be easily imagined when offered a member of the Gambino family on a silver platter, all coming out of busting an incompetent Ponzi scheme. Agents from the Miami field office reached an arrangement with Brian, in which they would pose to Chris as representatives of a pension looking for unorthodox methods of growing its capital–one requiring the special capabilities of an organized crime mastermind. There began a series of sit-downs with Chris, reeling him in with big temptations, and Chris responding, as always, with bigger bluster.

By this point, the various restructured companies under Chris’ watch fell under the umbrella name Messana Holdings.

In March, one of the agents posing as Brian’s contacts sat down with Chris and explained his proposal for the pension fund to buy shares of Messana in exchange for a kickback, disguised as a consulting fee, equivalent to one-third of the purchase price. In the second meeting, the undercover agent elaborated that their arrangement could be lucrative but admitted it “crossed a line” into illegality.

“Give it some thought,” the agent said. Law enforcement had to be very careful in such circumstances to garner clear evidence while avoiding accusations down the road of entrapment, trying to subtly lead a target to elect to enter a criminal scheme. If targets just passively went along, cases could fall apart.

They didn’t have to worry about subtlety with Chris.

“I like it already,” Chris said. After all of his get-rich-quick schemes, this one seemed like a sure thing that could reverse all his financial setbacks, an offer Chris couldn’t refuse.

When the subject of a drug dealer came up, Chris volunteered that he had plenty of experience in money laundering, bringing up $25 million as the upper range of money to be “washed.”

Chris boasted that he would facilitate a method for the drug dealer’s money to “come back nice and crystal” in 60 days for a fee. “They want it washed, probably it would take us, a million it would probably take us… if I took a million, we’d probably take $300,000 and give back $700,000.”

The conversation led to Chris pointing out the power of having “300 fucking soldiers in my family” and that declaration that encapsulated his now-20-year charade: You’re talking about the Gambino family.

On April 13, 2009, a $75,000 wire transfer was sent from the fictitious entity set up by the government, Benefits & Pension Group, LLC, in New York, to the Messana Holdings bank account. Three days later, as part of what Chris thought was a prearranged kickback, Chris wired $25,000 to the consulting company Great Lakes Advisors LLC. A second wire transfer of $20,000 was made on May 29, followed by another $5,000 from Messana to Great Lakes Advisors.

As soon as he sent those payments, Chris committed wire fraud.

On December 13, 2010, Chris Gambino was arrested.

The life Chris Gambino had built for himself came undone. Decades of pretending to be a member of a notorious crime family had finally attracted the nation’s top law enforcement agency. The FBI agents involved in the case netted a trophy. However, they never opened up how much getting a Gambino was specifically a priority or part of the original appeal of the case. (When reached for comment on this story, the FBI press department replied: “Unfortunately, the FBI’s Miami Field Office declines participation [in a story].” Technically, the case remains open.) In the end, Chris really had a crew torn apart by an informant, echoing the fabricated backstory that he had claimed led him to South Florida.

In the weeks after his arrest, Chris pleaded not guilty to wire fraud in a Fort Lauderdale courtroom. He was released on $100,000 bail. He reversed his plea a month later, and sentencing was scheduled for March 2011.

In his sentencing filing, his lawyer, Michael Rosen, the one who shared a name with the reputed mob attorney, argued that his client was a largely innocent-if-naive man who had been lured into committing a crime by overzealous law enforcement. Rosen did not deny that Chris consented to participate in the stock fraud scheme, but he insisted in his filing that “the ‘crime’ was created, instigated, and organized by the Government.” Chris was a legitimate small business owner who counted friends and family members as investors. The filing, with insistent all-caps by Rosen, read: “Mr. Gambino was NOT looking to break the law. Mr. Gambino was not breaking the law… ONLY WHEN THE GOVERNMENT SCHEME MADE ITS WAY TO MR. GAMBINO’S DOOR DID THINGS BECOME ILLEGITIMATE (and barely then).”

But the evidence against Chris was overwhelming—ample recordings of Chris boasting of criminal activity and knowingly agreeing to the illegal scheme.

During sentencing, Chris made the ultimate sacrifice: He admitted, through his lawyer, that he wasn’t a real Gambino. Rosen said that his client had changed his name to Gambino to create a brand for himself. “He chose a name by which to capitalize in the marketplace— which has clearly cost far more than it brought.”

The court was unmoved. Chris was sentenced to eight months in prison, followed by a supervised release of two years.

In a truly cosmic comeuppance, the man who for decades had pretended to be a reformed criminal had stumbled into becoming one.

Few in the public had reason to catch wind of Michael Rosen’s bombshell revelation, preserved only in unreleased sentencing transcripts. Once he was out of prison, Chris Gambino went right on being Chris Gambino. He may have realized that his greatest strength had always been the storytelling behind his Gambino aura. He briefly moved to Los Angeles and pursued screenwriting long after the initially promising movie project for My Only Son had petered out.

Kim Ornitz, a sound technician for movies who met Chris during that time, recalls that when people heard the name Gambino, they wanted to talk to Chris. “They’d sit down at a bar with him and ask, ‘How do you feel about John Gotti?’ [Chris would say,] ‘John Gotti ruined the family!’ Blah blah blah. Chris had a story… And everybody likes a story about gangsters.” At one point, Chris dropped an atomic bomb of irony about pursuing his work: “I want to get in on my own. I don’t want to make it on the Gambino name.”

Chris never gave up get-rich-quick schemes and outlandish claims. He talked about sourcing exotic animals for Mexican drug cartels, an alarming leap from his friendship with animal activist Shane Barbi. He got his hands on an American Express Platinum card at one point and, claiming he knew how to avoid ever paying off debt, spent wildly. Over time, he hatched a scheme to beat the lottery and one to build a processing plant to make Arabic gum, an ingredient in soft drink syrups, to sell to Coca-Cola.

Even those who suspected Chris’ Gambino family connections could be an invention never knew quite what to make of him. Deirdra Funcheon admits to having been worried for her safety when she received bizarre calls suggesting she should spike her New Times assignment. If nobody knew who Chris really was, then nobody knew what he was capable of.

Some look back with mixed emotions on Chris passing through their lives. Pat DeSimone, the Palm Bay plumber, always found Chris charming, articulate and stylish and admired his swagger. Chris’ former lawyer in Miami, Michael Rosen, admits to being curious about what became of Chris. “If you speak to him,” he adds, “tell him he still owes me money.” Certain aspects of Chris’ life survived the upheaval intact, including his marriage to Evelina, who, after all, had become a Gambino, in her case, without the same kind of baggage.

Kim Ornitz, Chris’ Hollywood friend, eventually concluded that Chris was “98% bullshit and 2% brilliance.” He hesitates to call him a scammer because, “If he was a con artist, then he wasn’t a good one, because… he never scored.” And even when his friends had started asking what Kim was doing hanging out with Chris, he didn’t completely walk away from Chris because “it was always interesting. I mean, the guy could tell a good story.”

There was an earnestness to Chris’ self-invention and his persona that could come off almost as commendable. Underneath the stubborn disguise, his desire to make something of himself resonated as genuine, and on some level people could pick up on that. Maybe he was someone to root for—or, at least, a doomed dreamer worthy of some empathy.

Chris gradually retreated from public attention, and refused to respond to any questions about Chris Horton, implying he does not know who that is. At this point, Chris Horton may feel more like a fiction to him than Chris Gambino. In a different way than he ever intended, Chris’ trajectory became Hollywood-worthy, a singular tragicomedy about how our dreams become our nightmares. Today, he is adamant that in the events that were a tipping point in his life he was set up by the FBI and his former friend Brian. “I was. I was ratted out.” Straight out of a scene from a mob movie, he depicts his guilty plea as a noble sacrifice, a sign of honor in an otherwise discouraging world. “I did what I had to do. I manned up.”

MITCH MOXLEY is a writer in New York whose work has appeared in The New York Times Magazine, GQ, Esquire, The Atlantic, The Best American Travel Writing, and other publications.

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