The Rise and Fall of a New York Shock Jock

Craig Carton’s misadventures in gambling and in the ticket-resale game led the on-air personality to risk everything on a pretty flimsy play.
Craig Carton
For a decade, Craig Carton, with Boomer Esiason, ruled sports-talk radio.Illustration by Nick Little

For Boomer Esiason and Craig Carton, the hosts of the “Boomer and Carton” morning sports-talk program, on WFAN, 660 AM, in New York, the big back-from-vacation week, right after Labor Day, was always a giddy one. You had your pennant races, the first week of N.F.L. games, and the inventory of guy-talk riffs that had piled up over the break. On Wednesday, September 6, 2017, Carton, the manic one, woke up at 3 a.m. He liked to be at the station by four; he rarely slept more than a few hours a night.

Carton and his wife and four children had just moved into a new apartment, in Tribeca, and he had that heightened awareness one has of one’s surroundings when passing the first night in a new home. On his way to the shower, he glanced out the bathroom window and noticed, in the courtyard, a man and a woman leaning against each other, apparently drunk. After his shower, he saw that they were gone. He dressed—T-shirt, cargo shorts, flip-flops—and ordered an Uber for the short trip to the station. On the stairs, he ran into the woman from the courtyard. She said, “Are you Craig Carton?”

“Yes, I am.”

“F.B.I. You’re under arrest.”

A squad of F.B.I. agents handcuffed him to a park bench and had him call his wife, Kim, who came down in her pajamas. He asked her to call his brother, who is a lawyer, and Chris Oliviero, the head of programming at CBS Radio, which owned WFAN. Then the agents drove him to Federal Plaza, where the driver said to the guard at the entrance, “We got a criminal in the back.”

Across town, at WFAN, Esiason, the authoritative one, was told that Carton had called in sick. “If you hear me starting the show, that means numbnuts is under the weather, and he’s not here,” Esiason said, on the air. He and numbnuts’s fill-in, Jerry Recco, sitting in the so-called power chair, chalked it up to the “Yankee flu”: the night before, Dellin Betances had blown a save.

Ten years earlier, the host in this slot had been Don Imus, whose success, for nearly two decades, had helped the station, early on just a sports-geek fever dream, evolve into a kind of deranged tristate-area Greek chorus. But one morning in April, 2007, Imus, goaded by his sidekick Bernard McGuirk, referred to the Rutgers University women’s basketball team as an assemblage of “nappy-headed hos.” This slur, unlike many earlier ones, brought on Imus’s firing. That left a huge hole to fill.

The station settled on Esiason and Carton. Esiason, then forty-six, had been a star quarterback in the N.F.L. and, in retirement, a respected commentator. Carton, then thirty-eight, was a well-travelled, fast-talking shock jock with a knack for the rhythms and the provocations of free-form talk radio. As a straight man, Esiason made sense; he had a name, some gravitas, and a history with the station as a regular Imus guest. Carton was more of a gamble.

At the time, Carton was the host of an FM talk show out of Trenton called “The Jersey Guys,” where he’d achieved some infamy after making fun of Governor Richard Codey’s wife, for her battles with postpartum depression. She’d mentioned once having an urge to put her infant son in a microwave. The Governor, Carton said on the air, could legalize medical marijuana, “so women can have a joint and relax instead of putting their babies in a microwave. . . . Women who claim they suffer from this postpartum depression . . . they must be crazy in the first place.” On a scheduled visit to the station, Codey, with a state trooper at his side, told Carton, “I wish I weren’t governor—I’d take you out.” The telecommunications-and-utilities committee in the State Assembly gathered, and passed a resolution to censure Carton.

There were other stunts. Carton organized a “100 Stripper Rally” in Trenton to protest a statewide ban on smoking in bars. And, in 2007, he urged listeners to turn in undocumented immigrants to the authorities; he called this “Operation Rat a Rat: La Cuca Gotcha.” For stuff like this, Carton was named, by the editors of a prominent Trenton blog, the ninth most powerful man in New Jersey politics.

But he and Esiason clicked. Unlike the station’s original big-cheese duo, Mike Francesa and Chris Russo—Mike and the Mad Dog—they never had a falling-out or even a cross day. Esiason, not the humblest of men (a “type-A my-way-or-the-highway guy,” as Carton called him), had the sense to let his partner lead, to recognize that Carton had an almost Trumpian nose for the kind of bombast and volatility that caused people to linger in the parking lot or to tune in the next day. “Some of that has to be manufactured,” Esiason told me recently. “All without writers. It’s all improv.”

“It’s right when you think it’s done, but it’s not done, that it’s the most dangerous.”

Carton’s voice is high and raspy, with the fray of all-nighters and bar arguments. He did passable impersonations of others at the station, including Francesa, Russo, and the Boston-bred Yankees commentator Suzyn Waldman, whose voice he has compared to that of “a male crack addict.” With fans who called in, he could be caustic or convivial. As an acolyte of Howard Stern’s—or maybe just as a regrettable male human—he often defaulted to leering misogyny, as in a 2009 exchange with the tennis player Jennifer Capriati, in which he asked if she’d sleep with him:

Carton: Not that you’re not hot, but you’re no Joanna Krupa. How hot was she?

Capriati: Um, you know, not bad, not bad.

Carton: Would you ever get it on with a gal like that, or no?

Capriati: What kind of questions are these, man?

And so on. Esiason did not intercede.

Since the début of “Boomer and Carton,” Mike and the Mad Dog have split, Imus and Francesa have retired (and, in Francesa’s case, unretired), and WFAN’s cultural presence has receded, even as its influence has spread. With more bandwidth, and a proliferation of platforms, sports talk, like political talk, has mutated and then kudzu’ed into our screens and earbuds. Let a thousand Bill Simmonses bloom. Some of us, for better or worse, live in a world of “Morning Joe,” “Fox & Friends,” Maddow, Tapper, Blitzer, Cuomo, and Rush. But in a parallel, almost exclusively male, universe the day is refracted through sports. Rich, Dan, Mike, Mike, Dan. “First Take,” “Around the Horn,” “Pardon the Interruption,” “Pardon My Take,” “Highly Questionable,” “Speak for Yourself.” There are more than a hundred basketball podcasts.

In the midst of all this, Esiason and Carton, AM-band throwbacks, held their own. Within about a year, they had the top-rated program both at the station and in their demographic and their time slot in New York, and had achieved a brand of regional fame, among the population of the tristate area that reads the Post back to front or spends a fat part of the morning rush at the wheel. The pair harked back to a pre-Internet age, when the city had its own cast of colorful characters, who have since been either eclipsed by or subsumed into the broader national tragi-farce of public life. In the era of Trump, many of our regional dramas and leading players have been elevated to the national stage. The city’s indigenous scandals gasp for air.

The news of Carton’s arrest broke just before 7 a.m. The program director at WFAN, Mark Chernoff, told Esiason, “Don’t say anything,” but Esiason—the talent, the ex-M.V.P.—overruled his boss and shared with his listeners what he knew, which admittedly wasn’t much. “I’m taken aback and surprised by it, just like I’m sure everybody else is,” he said. On the TV simulcast, airing on the CBS Sports Network, he crumpled up the sheet of paper with the news on it. “I have no other information.”

This past November, after a six-day trial in federal court in Manhattan, a jury found Carton guilty of conspiracy, wire fraud, and securities fraud. The court ruled that he had tricked a hedge fund and an individual investor into believing that he had a formal arrangement with Brooklyn Sports & Entertainment, which operates Barclays Center and Nassau Coliseum, to buy tickets to concerts in bulk, resell them on the secondary market, and kick back some of the proceeds to B.S.E. He’d used the hedge fund’s money to settle gambling debts and other personal expenses, and to pay back an earlier investor—a Ponzi scheme. He faced up to forty-five years in prison.

He’d posted bail and now entered limbo. In January, a little more than two months before his sentencing, I went to meet him for lunch at a restaurant called the Greek, near his apartment. He wasn’t living there anymore. He and his wife had separated, and he was staying in a house that he owned in New Jersey, which was in foreclosure. “I’m essentially bankrupt and on the verge of being homeless,” he said. He had on a red pompom hat, a red fleece jacket, and ripped jeans. He was drinking a gin-and-cucumber house cocktail called the Achilles Heel.

Carton has said that, off the air, he is “an introverted loner”—an embodiment of the Johnny Carson principle, whereby the performative and the private personae are hard to reconcile. In my presence, he was subdued, melancholy, and distracted.

“I made some really stupid decisions, and those decisions, over a very small amount of time, have now changed my life forever,” he said. “I’m guilty only of really, really bad judgment.” In the course of several meetings, he set out to convince me of this, even though it was too late to matter, really. The verdict was in, and a sentence awaited.

He began, at the Greek, by describing what both he and the government agree provided the context for his misadventures in the ticket game. “I’m a compulsive gambler,” he said. “I wasn’t always one.” He had certainly always had a taste for the action. In junior high school, he ran a makeshift casino out of his parents’ living room, using the roulette and blackjack features available on Intellivision, the early gaming console. (That got shut down when a neighbor found out that his son had gambled away a new baseball glove.) Like many people who follow or make their living from sports, he would routinely bet on games. In the nineties, during the first dot-com boom, Carton created an offshore casino called Betonfantasy.com, which introduced the concept of wagering on fantasy sports. Later, he launched a tipster site called Vegasexperts.com with a handicapper named Marc Lawrence, to whom he eventually sold his share, to focus on his radio career.

But, according to Carton, it had been ten years since he placed a bet on a sporting event. What brought him down was blackjack. “It was 2014,” he said. “We were going to do a show at the Borgata”—a casino in Atlantic City. “A couple weeks before that, Boomer and I are on the air. I say, ‘Give me ten thousand bucks, I’ll make it twenty-five thousand by tomorrow morn.’ It was a flippant comment, but Boomer called me on it. We talked about it on the air for the next couple of weeks. Before we got to the Borgata, he gave me ten thousand in cash. The next morning, I gave him the twenty-five thousand. Who guarantees a two-and-a-half-times return on gambling? It’s asinine. You can’t ever live up to that. But that night I did. I won about eighty thousand dollars. And so I became known as a blackjack savant.”

As Carton tells it, wealthy listeners started to offer him big sums of money, in the hope of getting a cut of his winnings. Another way of putting it is that he began taking out short-term personal loans of as much as half a million dollars, at ten-per-cent interest. Carton thought of these as investments, and of his gambling as a business, but it’s hard to imagine that the investors saw them that way. “If you have a propensity to be addicted to something, specifically gambling, the two worst things you can have are time and money,” Carton said. “All of a sudden, I’m walking into a casino with a million in cash in a duffel.”

He played only blackjack. Poker was too slow. “My brain works very fast,” he said. “I need that, where it’s non-stop numbers.” He’d get in the zone. “It’s the way Tiger Woods describes being on a golf course, Michael Jordan being on the court.” Carton played through the night and almost always played alone, in private rooms. “I just wanted to hide,” he said. “It was an escape for me. A bubble. It was almost emotionless. If I won 3.9 million, there’s no celebration. Lost a million? I didn’t punch a wall. The more money I had, the longer I could play. The longer I could play, the better I felt.” He usually drank, often heavily—a bottle of vodka, tequila, or Grand Marnier—but he says that the alcohol never affected his judgment.

He typically bet ten thousand per hand. With so much at stake, he could ask for a reshuffle anytime, or reserve several tables and play multiple hands, which, he said, improved his odds to fifty-fifty. A tally that he made, before his trial, of his activity at the tables indicated that his wagers on blackjack, during a period of eighteen months, totalled more than a billion dollars. A yard, on heads or tails.

“The quote-unquote perks were intoxicating,” he said. “Nothing was off the table. Nothing.” Some things he left on the table, apparently: he claims never to have tried cocaine or paid for sex. “I go to Resorts World in Bimini, they give me three beachfront houses, a private jet, a seaplane. I had the single biggest win in Resorts history—$3.9 million in three days.” He talks about casinos the way some people talk about fishing holes: The Mohegan Sun has a private room on a floor no one knows exists. Harrah’s in Atlantic City let him play five hands at a time, at twenty-five thousand dollars each. Who can forget those frosted-glass doors at the Seminole Hard Rock?

One lender testified that, to keep Carton’s wife from finding out about his gambling, he and Carton referred to the casino trips, in their e-mails, as Project Black. But Esiason started to have an inkling. He recalls going to Las Vegas with Carton in 2015 to do a broadcast of their show before the Floyd Mayweather–Manny Pacquiao title bout. “Craig got four major suites at four different casinos,” he told me. “He flew us out on a G5. We’d been at the Borgata, at the Mohegan Sun, but this was a different order of magnitude. Of course, he was now required to go to all these places and gamble.”

Carton was earning roughly two and a half million dollars a year at WFAN. That wasn’t enough. In a year and a half in 2016 and 2017, he borrowed more than thirty million dollars. These were so-called handshake deals, though some were with lenders he never met. The gambling was legal. So were the personal loans. And, though he was sometimes late settling his debts, he says he always repaid them. This could be true. The problem was, and remains, where and how he got the money to do so.

It’s a commonplace of professional sports that young athletes, with fame and wealth thrust upon them, are at high risk of attracting unsavory companions and undue trouble. By some corollary, it seems that sports-radio hosts can get lured in, too. The milieu is one of casinos, strip clubs, postgame revels, bookies, retired pros, and hangers-on. There’s a rotating cast of old jocks, broadcast hacks, and sui-generis spielers. In such company, amid a barrage of grungy tales, a fan can find that innocence withers fast. Hosts live a kind of double life, protecting the mythology of sport while knowing it’s bunk.

In 2013, Carton wrote a book, called “Loudmouth”—a memoir of sorts, published by Simon & Schuster. A blurb from the former New Jersey governor Chris Christie states, “You are going to love him even more after you read this book.” That’s debatable. No amount of exposure to locker-room talk can inure a reader to the smuttiness of it all—it’s character assassination, by his own hand. He cheats, he lies, he starts fights, he drives drunk. He trashes former bosses and partners and denigrates his parents. Women are strippers, hookers, fat chicks, hot waitresses, or incompetent colleagues. There’s a chapter about going with friends to Hell’s Kitchen to hire a prostitute (“Vomit was everywhere. . . . There was no way I was going to let this hooker blow me now”) and one about a vanload of fellow valet-parking attendants employing, and then robbing, another prostitute. He dry-humps a lifeguard, gets propositioned by the drunken wife of a colleague, and passes on his secret to making one’s penis seem bigger in the showers after the game. Was this a performance, or his true self? Which Carson was this Carton? It’s startling to think that the author was a prominent employee of a major media corporation, until you remember that that corporation was CBS—and that CBS owned the publisher, too.

Throughout the book, Carton takes numbers and names, remembers slights, and delights in the comeuppance of his detractors. “My greatest professional satisfaction is being able to tell the naysayers to fuck off,” he writes. His account of his childhood bends toward grievance. He grew up in New Rochelle, “without hugs, kisses or verbal confirmation of being loved.” As he recalls it, his siblings and his father, an orthopedic surgeon, used to pretend he’d been adopted from Vietnam, because he looked different from the other kids. One of his earliest memories is of urinating into a houseplant in nursery school, and his father’s telling him later, “You will not embarrass us again.” But he would. He twitched and fidgeted, spilled things, walked into swings. When he was seven, he exhibited so many involuntary tics that his parents installed in his bedroom a traction apparatus with a metal collar to subdue him. They wheeled a TV into the room. Immobilized, he listened to Joe Garagiola call the major-league game of the week. The device did nothing for the tics—years later, he was given a diagnosis of Tourette’s syndrome, and also obsessive-compulsive disorder, attention-deficit disorder, and restless-leg syndrome—but it did help instill a love of the sound of a man talking about baseball.

“Their feeding time should be in about twenty-five to thirty minutes.”

In my conversations with Carton, he cited a couple of glosses on his gambling addiction. One was that, to alleviate his restless-leg syndrome, he’d been prescribed a drug, ropinirole, one of whose side effects is, believe it or not, compulsive gambling. The other explanation was sexual abuse.

“I was ten,” he told me. “I put the walls up to protect myself from the world.” He described being sexually molested at sleepaway summer camp—“every night for eight weeks.” He said the assailant was a counsellor with whom he shared a bunk bed: “I remember the smell of booze and a lead pipe pressed against my throat. And then the next morning he’s there in the mess hall asking me to pass him the salt.” He declined to name the camp. “It still exists and has new owners and they’ve done nothing wrong,” he said.

He’d told his wife about the abuse before they were married. And he’d submitted a chapter about it when he was writing “Loudmouth,” but after discussing it with his editors he decided he wasn’t ready to address the subject publicly. “Closest I came was when Boomer and I were talking about Sandusky,” he said, referring to the Penn State assistant football coach who was convicted of sexually assaulting boys. Though Carton often blistered Sandusky, and the head coach, Joe Paterno, with a vehemence that startled his colleagues, he never mentioned his own experience. “I wasn’t brave enough to say anything,” he told me.

“Radio is my drug,” Carton likes to say. From his first taste of it, as an undergraduate at Syracuse University, the craft, and the cocoon, of it drew him in. After he graduated, a demo tape of his college-radio stints got him a job doing a weekend shift on the air at a sports station in Buffalo. Gradually, he worked his way into bigger markets and bigger paychecks—Cleveland, Philadelphia, Miami, Denver, New York, Philly again. He often cared less about the sports than about sports as a mode of guy talk, a morality play, a ground for argument, replenished each day. His idol was Howard Stern. He cast himself as a dirtbag Everyman, a truthteller and an enemy of everything “bougie.”

Carton restlessly pursued entrepreneurial interests. One was a startup, Calling Stars: the idea was to have celebrities deliver personalized phone messages to fans. He paid a visit to the headquarters of Hustler and met with the son of Larry Flynt—“I was about to become a porn mogul”—but the scheme fizzled.

Then he caught a break: New York on line one. WNEW, the storied FM station, which was experimenting with an all-talk format, hired him to be the co-host of a morning show called “The Sports Guys.” The other sports guy was Sid Rosenberg, whose life was beginning to spin out of control as he succumbed to various addictions. Carton depicts him in “Loudmouth” as a crackhead and “a degenerate gambler . . . who spent countless hours crying by the elevator,” scared of hit men. Rosenberg felt that Carton was trying to supplant him. WNEW cancelled the show after a year and a half and ultimately abandoned the talk format, and Carton retreated to Philadelphia, bitter that he and Rosenberg had blown their chance.

“Sid and I battled,” Carton said. “He took shots at me, I took shots at him. We’ve since made amends.”

“They’re both crazy,” Esiason said.

“In his book, he destroyed me,” Rosenberg told me. “I barely smoked crack in my life! And I got him the fucking job! I was new. I wasn’t very good. I was the host, but it didn’t take more than a month before he’s sitting in my chair.” He went on, “He won every battle. It ended very ugly. And I got into all kinds of fucking trouble. Drugs, drink. My family, they’re living in New Jersey, they’re listening to 101.5, ‘The Jersey Guys,’ and they’re all, like, ‘Why is this guy on 101.5 taking such glee in your demise?’ He comes off like a dick. So do I, don’t get me wrong. But he takes my dick to the exponential. Still, once he got to the FAN, to the top of the ladder, his resentment, his dislike, dissipated because he was top of the heap. And then I’m doing a show out of a shoebox in Pompano Beach and he’s the one at WFAN. Roles are reversed, if you know what I mean. I have fucked up a million times. I’m a triple threat. Drugs, drinking, gambling. The gambling! To be honest, all these years I thought I was worse than him.” Rosenberg was on the air, on WABC, with Bernie McGuirk, the old Imus sidekick, when he heard about Carton’s arrest. “I was fucking floored,” he said.

Sports radio does fairly big numbers, in the major markets, but it’s a backwater of high intensity and low consequence, with more petty jealousies and rivalries than you find in academe. It may well be that the feuds and the potshots aren’t so much a by-product as an integral part of the entertainment, a subplot to amplify and mirror the foreground arguments over the actual games and the people who play and rule them. Or else the squabbles are just a function of the unstructured and unscripted hours that need filling: thrust, parry, apology.

Carton was taking shots at Mike Francesa well before he got to WFAN. When Carton began working at the station, Mark Chernoff, the program director, arranged a summit at the Cup Diner, in Astoria, to make peace. As Carton tells it, Francesa arrived late and kept his sunglasses on throughout. Of the Boomer-Carton concept, he repeatedly proclaimed, in his Cheddar-dip timbre, “It’ll never work.” The feud festered. At one point, citing Carton’s “meanness,” Francesa said, “If I want to take care of him I could do it in five minutes. It wouldn’t even take me five minutes.” For a while, Chernoff kept Carton from making fun of Mike and the Mad Dog, and of Suzyn Waldman, but, as Esiason remembers it, Carton told Chernoff, “When we’re No. 1, you can’t fucking tell me what to do.” And, once they were, he didn’t.

After Carton’s arrest, he resigned from WFAN. He went to the station to clean out his office, and wrote Francesa a note and put it under his door. “I told him I’d miss the back-and-forth that we had between us, and that I appreciated that he didn’t take any potshots at me, out of respect for my family,” Carton told me. “He could’ve. I probably would’ve.” And then he recorded a podcast excoriating Francesa.

But many of Carton’s targets couldn’t resist a little payback. Geno Smith, the much maligned former Jets quarterback, tweeted, “Same guy who was calling me a thug on some lame radio station was running a Ponzi scheme??”

Some friends stuck with Carton (he cites Chris Christie, at whose home he watched the N.C.A.A. championship football game, in January), and others cut him loose. Esiason struggled for months after the arrest to come around to some kind of forgiveness.

“I thought you were a foxhole guy,” Carton said to him at one point.

“I am a foxhole guy, as long as you’re not bringing a hand grenade into the foxhole and pulling the pin,” Esiason replied.

“Craig can say whatever he wants, but no one took the stand to defend him, and he didn’t take the stand, either,” Esiason told me, when I went to see him at WFAN. (The station wouldn’t otherwise comment or allow its employees to talk.) “I’d really thought the ticket stuff was all on the up-and-up. Craig was a very vocal anti-Madoff guy, like we all were, but this seems very similar.”

One morning, a couple of months before his sentencing, I went to see Carton in New Jersey horse country. He was living with King, his hundred-and-seventy-pound English mastiff, in a very large stone house—some ten thousand square feet, on four and a half acres. This was the prime lot in a pre-crash subdivision now in various stages of non-completion. Carton bought the house from the builder, in 2015, for $2.1 million: six bedrooms, gym, arcade, movie theatre, swimming pool, basketball court, five-car garage, and living room with three TVs. “It was supposed to be the house where my kids would bring their kids and we retired and all that stuff,” he said. Now he was trying to unload it for less than the mortgage—a short sale, which would require bank approval. He hadn’t made a payment in nine months.

Carton led me into the kitchen. A sign over the stove read “No Snivelling.” He had assembled some artifacts of sideline endeavors, a polemic of swag. There were boxes of adhesive bandage strips imprinted with pro-team logos. Carton had secured the adhesive-strip rights to the N.B.A. and the N.F.L. and M.L.B. He said, “I created and manufactured jewelry for Frederick’s of Hollywood.” Carton had also got the jewelry rights to Muhammad Ali. I opened a jewel box and a voice like Ali’s greeted me by name. Not included in this array was a sample of a men’s hygiene product he’d launched, called Junk Balm.

The insistence underlying the presentation was that his sidelines had been real businesses, even though prosecutors had dismissed them as figments or exaggerations or fronts. One of Carton’s foundational grievances was that the statement released by the government after his arrest had described his secondary-market ticket operation as a “sham.” They said he had “no deals to purchase any tickets at all,” when in fact he had bought and sold tickets in vast quantities, with the knowledge and the assistance of the top executives at B.S.E. They sold him the tickets, knew he was reselling them, and had at least discussed getting a share of the revenue. The prosecutors didn’t follow through on the “sham” part. They affirmed, for example, that Carton had paid $1.5 million—the majority of it on his credit card—for thousands of tickets to Metallica and Barbra Streisand. You can’t do that unless someone connected to the concerts lets you. But by then the “sham” label had stuck.

Carton dates his association with B.S.E. to the 2014 Super Bowl, in New Jersey. Carton says that he approached Brett Yormark, the company’s C.E.O., and asked if anyone had a so-called “hold” on Barclays on the night before the game. No one did; it was, as they say, a dark night. So Carton helped CBS book the Red Hot Chili Peppers, who would be performing the halftime show. Carton got twenty thousand dollars for introducing the band onstage. (A spokesperson for B.S.E. denies that Carton had any involvement in booking the show.)

“The most important thing is that everyone who wants a catapult gets a catapult.”

Not long afterward, Carton offered Yormark help booking acts in order to avoid dark nights. Barclays Center had opened less than two years earlier, and, as the Super Bowl weekend suggested, the arena management hadn’t quite got a handle on filling it when the Nets weren’t home. They launched a partnership in which Carton would get fifty-one per cent of the proceeds; B.S.E. hired a music-industry executive named Joseph Meli to be the chief content officer. “I brought Joe to the table,” Carton told me. After some abortive attempts to set up shows, and after hearing some talk that Meli wasn’t reliable, B.S.E. dissolved the venture.

From this foray into the concert trade, Carton learned a little bit about the secondary market for tickets. Scalping, thanks to StubHub and the like, had gone semi-straight—what formerly could be a Class D felony was now legit, though still in many ways legally murky. Carton approached B.S.E. again, to ask about buying tickets in bulk. “There’s three ways to get tickets—from the arena, from the promoter, and from the artist,” Carton told me. “So, if you have a relationship with any one of those three, then you can get access to the best tickets and you can sell them for a big profit on the secondary market.” Referring to B.S.E., he said, “It guaranteed them ticket sales, and then a piece of the profit on the secondary sales.”

The extent to which this did or did not happen was not fully litigated during Carton’s trial. Correspondence indicating that it did happen was not allowed into evidence, because it was deemed hearsay: B.S.E. executives said on the witness stand that they did not remember certain e-mails, and Carton never testified. In his kitchen, he showed me a bunch of e-mails from B.S.E. executives. One included a term sheet offering him two hundred tickets to every future concert, with B.S.E. getting twenty per cent of Carton’s profits on the secondary sales. If B.S.E. introduced Carton to other arena operators and promoters, B.S.E. would get 7.5 per cent of that profit. This term sheet was not presented at the trial. Another e-mail, from Fred Mangione, Yormark’s chief of staff, in November, 2016: “This will start the beginning of our deal and rev”—apparent shorthand for revenue sharing. Mangione said he couldn’t remember what it referred to. B.S.E. executives seemed to be minimizing their involvement with Carton, and with the practice of turning over tickets to secondary dealers. (The B.S.E. spokesperson said that the company never had any agreement about profit sharing, and didn’t receive any payments from Carton.)

It didn’t help Carton’s case that he doctored some e-mails—along the way, misnaming the company he was supposedly representing and misspelling Barbra, as in Streisand. (Mangione testified that he would never have made that mistake, because it had happened previously, on his watch—before a Streisand concert at Barclays—and “it wasn’t a good day, let me put it that way.”) Whatever ambiguity there was about whether any kind of deal or revenue sharing between Carton and B.S.E. really existed, there was no question that Carton had misrepresented such an arrangement to his investors and then misspent their money. Therein lay the crime. Carton sent investors forged contracts that an associate of Joe Meli’s had worked up (and that Carton had further doctored) in an attempt to make an apparently improvised relationship with B.S.E. look like a contractual partnership.

In December, 2016, Brigade Capital, a twenty-billion-dollar asset manager, committed to an investment of ten million dollars, through a hedge fund that the company managed. The investment was a revolving loan with a return of ten per cent and a share of the profits. A score for Carton, an afterthought for Brigade. Even though the deal with Brigade specified that the loan be used only for ticket purchases, Carton used a portion of the initial investment, at least two million dollars, to pay another investor, and his own gambling debts.

Two of Carton’s personal lenders testified at the trial, under immunity deals. One was Desmond Finger, an employee of the Sapphire club, a midtown strip joint. The other was Harvey Klein, from Monsey, New York, who ran an array of businesses, including an energy company that had been sued or sanctioned by several states for overbilling and consumer fraud. In 2016, these two extended Carton more than a dozen loans, of as much as half a million dollars each. Carton viewed them as investments. As he wrote to Klein before a holiday blackjack trip to Bimini, “Would be remiss if I didn’t offer you first dibs.”

By the end of that year, Carton, between these liabilities and others at the casinos, was facing a pileup of debt. The Brigade money was a lifeline. As he wrote to Meli around Christmas, “We survived the death bullet.” But another always loomed. As Meli texted, “We use Brigade money to repay debts. Where do we get the money to buy tickets?” Carton replied, “Agreed.” He seems either to have believed it was O.K. to do this (he told me he’d relied on the old idea that “money is fungible”) or to have knowingly been running a Ponzi scheme. Carton maintains that it was the former; the court ruled otherwise.

The F.B.I. arrested Meli at the beginning of 2017. He’d defrauded investors by falsifying bulk-ticket deals with producers of Broadway shows and with concert promoters, and then used the investors’ money to pay off earlier investors or to enrich himself. At first, Carton led Brigade to believe that he was a victim of Meli’s, not an accomplice. Brigade stuck with Carton, who one day showed up at its offices with a bag of Streisand tickets.

Last April, Meli was sentenced to six and a half years in prison and ordered to pay his victims almost sixty million dollars. Carton says they haven’t spoken since Meli’s arrest. “He was the smartest guy in every room I was ever in,” Carton told me. “If that makes him a world-class con man, then maybe that’s what he is, but I’d never seen anything like it. It was Columbo-esque.”

Over the summer, Carton missed a payment to Brigade. The firm had been coöperating with the F.B.I., which had apparently decided that Carton wasn’t Meli’s victim, after all.

Among the many baffling elements of the whole affair are why a firm of Brigade’s size and stature would muck around in such shallow, muddy waters, with such slippery fish, and why Carton, a man who by his and others’ accounts loves his family and his job, would risk both on so flimsy a play. As to the former, it may have had something to do with the allure of concert tickets, whose scarcity is often treated as currency in certain ardent, privileged circles, and with the charm and the celebrity, such as it was, of Carton. (A strip-club owner named Michael Wright, who was charged as a co-conspirator in the case, wrote to the judge prior to his sentencing, in March, that Carton “radiated energy and drive that drew me in. I was a bit awed and flattered.”) As for Carton, maybe it’s just that he liked the speed of the numbers, the playing of multiple hands—or the prospect of a whole new cast of naysayers, to whom he could eventually, in his dreams, say fuck you.

In “Loudmouth,” Carton writes that his biggest fear is going to jail. His only experience with prison is having once played softball against inmates at a penitentiary on Staten Island.

On Friday, April 5th, at Carton’s sentencing, the judge, Colleen McMahon, remarked that she was a fan of “Boomer and Carton,” and that she was listening the morning of his arrest.

The Post had just run a column by Phil Mushnick, the paper’s longtime sports-page scold, who’d got his hands on a video that Carton had made, called “The Reckoning,” in which Carton discusses his addiction to gambling. (The video had been made by Marie McGovern and Martin Dunn, the former editor of the News, friends of Carton’s who were present at the sentencing. “It was just a sizzle reel,” Dunn told me.) McMahon said that she looked forward to watching it. But, she said, “today comes the legal reckoning.” She handed down a prison sentence of three and a half years. ♦