R.J. Cipriani on March 9 in Santa Monica. Photographed by Daniel Prakopcyk Gambler R.J. Cipriani has made a calculated bet in agreeing to sit for his first in-depth profile. He thinks revealing himself more fully will sharpen his position in his fight with Paramount president Jeff Shell, whom he may soon dislodge from a second major studio job in three years, having helped precipitate Shell’s fall as NBCUniversal CEO in 2023. Cipriani also believes that an unvarnished close-up on his improbable biography and outsized personality may finally deliver the Hollywood green light he’s convinced he deserves.
At his favorite corner table at the Venice restaurant Gjelina, Cipriani refers to himself as “a kamikaze,” “a lone wolf,” “a wild card” and “a fucking cowboy.” He drops names, cracks jokes, issues threats. On several occasions, he breaks into song. An observant Catholic, he says he’s recently been visiting his local church in Santa Monica multiple times a day to pray as he contends with “forces of evil,” adding, “I’m a soldier of God.”
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The 6-foot-5, blue-eyed Cipriani — an under-the-radar figure around the entertainment industry who’s now at the center of one of its biggest stories — radiates main character energy. Which may be why he’s proven so attracted to conflicts and why he’s stacked up so many antagonists. The narrative of his life arcs toward escalation.
Amid a disagreement over Cipriani’s pitch for an unscripted series called Star Serenade, he alleged that Shell disclosed confidential information — in violation of securities law — about Paramount’s deal with the Ultimate Fighting Championship as well as its purchase of Warner Bros. Discovery. Paramount has since hired an outside law firm to investigate; the SEC is looking into the matter as well. Shell’s lawyer termed this Cipriani’s “extortion scheme.”
Cipriani, 64, who has a history of tipping off the feds, replies, “If that’s extortion, I guess I’m an extortionist. I don’t know what to tell you. Yeah, I’m going to try to get people who fucking act badly to act correctly.” He continues, “The definition of extortion is: ‘If you don’t do this, I’ll do that.’ I’m sorry that people have a bad connotation for the word, but in reality, it happens every second of the day.”
Cipriani insists he “just wanted a TV show, not a payoff.” This is why he says he turned down a $1.3 million settlement offer which was put forth by their then-mutual attorney, the prominent Hollywood litigator Patty Glaser, before filing his $150 million lawsuit. The claim: that assistance he provided saved Paramount Skydance $1.5 billion in its South Park contract negotiations last year.
“I’ve been on my last bet of all the money I had so many times, it’s a joke,” Cipriani says. “When you live like that, there’s no amount of risk you’re not willing to take.” He’s a self-appointed crusader and self-mythologizing provocateur who’s convinced he’s the maverick hero, or at least antihero, of his adventures — but is also self-aware enough to understand that he might be perceived as a villain.
***
Cipriani is an under-the-radar figure around the entertainment industry who’s now at the center of one of its biggest stories. Photographed by Daniel Prakopcyk Cipriani grew up a choir boy in a working-class section of Philadelphia, the fourth of five children in a devout Italian Catholic family. His father was a factory worker and a barber, as well as a bootlegger and loan shark. “Watching him talk to anyone, at his shop and on collection runs, made me the person that I am,” Cipriani says.
At his parochial school, Holy Ghost, he was the class clown: “I was an entertainer, I sang, I made people laugh.” By 18, Cipriani was stripping on ladies’ nights at a local bar. “One of the girls I met there who liked me, she took me for a drive in her brand-new Cadillac — she was married to a mobster in Scranton who was in Russell Bufalino’s crew,” he recalls. “It was fun.” Mark Hutchinson, a friend of Cipriani since Holy Ghost, says, “He’s always been this off-the-streets, self-made hustler. He’s very charismatic and people just fall in love with him.”
Cipriani had other hustles, too, including time spent in construction and the wholesale soft-pretzel distribution business. But before long, he found his destiny in Atlantic City. “The first time I ‘won big’ there, at blackjack, it was 1978,” he says. “It was $124 and it felt like $124,000. I came home and told all my friends: ‘I just destroyed Atlantic City and they gave me a free lunch!'”
Cipriani tells vivid tales of violence during his younger years. In one, he nearly went to prison after repeatedly shooting a motorcycle gang member in the leg during a fight over a mutual love interest. (He says it was self-defense.) In another, he describes how, after a relative was raped, he lured the assailant to a hotel room, physically restrained him, then subjected the man to torture by placing a rat in a container around his genitals. (“I wanted to make sure he would never, ever do it again.”) He also claims to have dynamited a lawyer’s residential property amid a legal dispute. “Didn’t do it inside the house,” he assures. “Just wanted to send a message.” Asked if he’s volunteered these incidents to send a message to those he’s currently warring with about his penchant for aggression, or to preemptively self-disclose so others can’t hold such potentially damaging information against him, he replies: “It’s a combination.”
Joe Stampone, another pal since childhood, notes of Cipriani that “his education was the streets. He’s always been fearless in any kind of company.” These days, Cipriani goes after the richest and most powerful people on earth. “It doesn’t surprise me even a little bit,” says Stampone. “He’ll find a way to own whatever situation he encounters. It’s what makes him as unique as they come.”
In time, Cipriani made his way out of Philly by playing cards, turning blackjack into a career, winning over the years what he says has been “eight figures.” An admiring Vegas associate muses, “If you let him sit in your casino and play blackjack, he’ll beat your brains out. He tells me he doesn’t count cards. But I don’t know how you win like him without counting cards.” A casino executive who likes Cipriani but has banned him from playing because “he wins too much” says, “I know him as an anomaly.” Cipriani claims “no edge” at blackjack — that it’s far more luck than skill, and that the key to success is knowing when to walk away from the table. “Play as short of an amount of time as possible,” he advises. “Gambling is very hard. People ask for tips. Here’s my tip: Don’t gamble.”
Cipriani has loved the Vegas VIP life, hanging out with everyone from Andrew Dice Clay and Mark Cuban to Natasha Henstridge. Casinos have flown him in on a G650 and ferried him around in a Rolls-Royce. He fondly recalls that his whale status meant he landed better comped seats at local concerts than his partying buddy Nigel Lythgoe: “He asked me how, and I said, ‘Because I’m a fucking gambler!'”
Back home, Cipriani spent years caretaking his mom, Regina — “the mother of all mothers” — during her terminal decline into the Alzheimer’s abyss. By his account, this defining experience estranged him from his father and siblings. “It was the hardest thing and the greatest thing I’ve ever done,” he says, his voice catching and eyes watering. When she died, he paid for highway billboards extolling her. “My dad was the type that never told me he loved me. My mom was the type that told me a hundred times.”
Cipriani explains that Star Serenade is a passion project for him, one he wants to see realized as a “legacy” in honor of Regina, because of his own serenading history with her. In 1987, he self-financed his own recording of a four-track EP, titled Forget Me Not, featuring rock tunes and power ballads. “She would listen to these fucking songs over and over,” he says, his tears now overflowing. “Then when she got sick with Alzheimer’s, and she didn’t know who I was — and she didn’t know who she was — I’d sing the songs and she’d sing them with me, in perfect pitch.” He pauses, overcome. “She didn’t know how to eat. But she knew every word.” Later, he adds, “my mom always believed in me.”
***
“I’ve been on my last bet of all the money I had so many times, it’s a joke,” Cipriani says. “When you live like that, there’s no amount of risk you’re not willing to take.” Photographed by Daniel Prakopcyk Cipriani’s record includes a guilty plea two decades ago for insurance fraud during a stint as a public adjuster for policyholders, and a brief detention around the same time for domestic violence after a fight with a former live-in girlfriend. (He notes that no charges were filed and insists they’re now on good terms.) “There’s nobody that goes through shit — that’s lived a life — that hasn’t been arrested for something,” he says. “It’s just impossible.”
Cipriani explains that he first developed a relationship with the feds in 2010, after he’d been swindled out of $2 million by a con man named Troy Stratos, who was ultimately sentenced to more than two decades in prison for financial fraud. He describes working with investigators over an extended period to amass documentation that nailed the case, whose main swindled victim was Eddie Murphy’s former wife, a Cipriani friend.
Not long afterward, he alerted the FBI and SEC to a purported penny-stock scheme involving a marijuana-related company that had been engineered by a business partner. Cipriani believes that Dick Wolf, who’d invested with the businessman, was inspired to make his CBS series FBI by the experience. He describes having met the Law & Order creator’s representatives, noting he’d saved their client money and suggesting such a procedural: “The motherfucker does FBI right after that. Doesn’t even include me.”
Around this time, Cipriani says he also went to the FBI about the activities of an international drug kingpin named Owen Hanson. In his telling, he was tricked into working as a cleaner for Hanson, who bankrolled his gambling through a staking agreement, in which a backer funds the bets and takes a cut of any profits. In Cocaine Quarterback, Amazon’s 2025 docuseries about Hanson, the since-convicted felon refers to Cipriani as “a money-laundering magician.”
For his part, Cipriani insists he’s never whistle-blown in exchange for immunity in any case and notes he’s never received a financial reward from the government, although he’s sought it. He does acknowledge that cooperating as a source can provide welcome protection. A private investigator named Daniel Portley-Hanks — who recently testified to his part in Britain’s phone-hacking press scandals — pled guilty to being hired by Hanson to, among other acts, defile Cipriani’s mother’s grave with blood-red paint. (Portley-Hanks tells THR that “I shouldn’t have done it,” but Cipriani’s “no goody-two-shoes.”)
Cipriani furnished THR with a signed letter from a prosecutor in the U.S. Attorney’s Office, which attested that he was a victim in the case, along with a note from an FBI agent who handled the Hanson probe: “Over the years, [Cipriani] provided valuable information to me on multiple investigations, and was able to provide assistance to numerous other investigations worked out of different offices.”
Paramount president Jeff Shell Chris Unger/Zuffa LLC/Getty Images Cipriani believes that Cocaine Quarterback depicted him in a negative light because its producer Mark Wahlberg is close with two figures, director Peter Berg and mogul Ari Emanuel, whom he’s tangled with in the past. “It’s what I know about both of them,” he says, before asserting incendiary, unverifiable allegations of misconduct. As part of the Shell litigation, his attorney has sent WME a document retention request for communications involving both men. (Cipriani says he’d considered suing Amazon over the project, with the intent to settle, though he never went through with it: “What I was hoping to do is get my own docuseries that they’d be forced to give me.”)
Over the past several years, Cipriani has waged a public war against Resorts World Las Vegas after he was arrested in a dispute on the casino’s premises with a fellow gambler who’s a convicted fraudster. He’s pursued a civil RICO case accusing the company of operating as a “racketeering enterprise” and supplied intel to federal authorities about what he alleged was illegal bookmaking. Separately, Resorts World’s CEO was fired and later received one year of probation in a plea deal for violating anti-money laundering laws.
Cipriani is now banned at every major gaming house on and off the Strip, plus California’s Indian casinos. According to him, this is primarily due to his efforts against Vegas gambling industry corruption, along with what he considers his taint from the Hanson case. He’s been reduced to local Los Angeles area card rooms, which he derides as “shit holes” — “there’s no comped jet. It’s just a punk show.”
He claims he’s also been a hidden hand in ferreting out other illegal activity, including by leading law enforcement to the case of the since-busted interpreter for Shohei Ohtani who paid off nearly $17 million in illicit gambling debts with wired money from the Dodgers star’s account. He’s often frustrated by the glacial pace of government investigations. Cipriani’s solution has been to turn them into high-profile cases by leaking to the press. As he puts it, “They don’t act fast enough, and I’ve got to push them. The way I push them is I put shit in the news.” He shrugs. “They don’t like it, but then it’s suddenly something that the agents’ superiors care about.” (The FBI declined to comment on his relationship with the bureau.)
Cipriani knows that he’s considered a snitch. “People call me that all the time,” he says, unbothered, recalling an episode from a half-century ago as proof of his character: “When I was a freshman at Holy Ghost and a junior threw me down a flight of stairs, the priest demanded that I tell him who it was. I wouldn’t.” In his view, he’s simply a virtuous reformer “going after bad guys,” and what he sees as his ongoing collaboration with law enforcement is only pragmatic.
Those who’ve long dealt with him think this is rich. “He’s a convicted felon,” observes a Vegas casino executive who’s banned him. “You’d think someone with that background would be tolerant or forgiving of others’ mistakes — and he’s really not. He somehow believes he’s doing God’s work.”
Cipriani prides himself on being the media’s puppeteer, weaponizing journalists’ competitiveness for scoops. In the Shell saga, he’s spaced out his court filings to maximize coverage and has breadcrumbed interest by circulating documentation to outlets — THR included — laced with Easter eggs designed to spark darker speculation. “When I have an adversary,” he says, “I’m a master of cognitive warfare.”
Cipriani cites the go-to Hollywood crisis communications advisers Mike Sitrick and Matthew Hiltzik (the latter now represents Shell) as counterexamples to his own approach. “They’re playing defense,” he explains. “They’re trying to protect somebody that, most of the time, is a scumbag, right? I’m trying to go after someone.” He adds that he believes he’s “let millions of dollars slip through my hands” by not charging friends and associates for his spin services over the years. “I always thought of doing this and the motto is, ‘We don’t do damage control. We do damage.'”
***
A casino executive who likes Cipriani but has banned him from playing because “he wins too much” says, “I know him as an anomaly.” Photographed by Daniel Prakopcyk Cipriani has long pursued entertainment dreams that haven’t materialized. Following the singing career that never took off, he attempted to remake himself as a producer. So far, he’s mostly found himself in development hell and making enemies of bigger players.
One unrealized project revolved around Cipriani’s penchant for gifting gambling winnings to people in need. Ever the showman, he’d drummed up attention under the persona Robin Hood 702 (the Vegas area code). For a time, he was talking to Ryan Seacrest. Then reality powerhouse Ellen Rakieten, who’d made Oprah Winfrey’s The Big Give.
A scripted series set up at Sony centered on his experience in the Hanson case. Its working title was Jackpot, which he says was his FBI code name. He spent years cycling through collaborators, among them Nick Stoller, José Padilha (Narcos) and Derek Kolstad (John Wick). Cipriani recalls the latter’s dramatic license, in an opening scene set in Australia, to explain their creative tensions: “I’m being chased while driving and there’s a koala in the front seat next to me with a eucalyptus leaf in its mouth. Swear to God. I’m swerving and we go off a cliff.” He shakes his head, eyes wide. “I go, ‘What in the fuck is this? We’ve got enough real shit that happened.’”
Before Shell, Cipriani had already scorched his way through Hollywood. When he felt Jason Statham had disrespected him, he leaked a recording of the action star ranting on the set of a gambling movie they’d worked on together. (Statham later issued an apology for “using terms offensive to the LGBTQ community.”) After Cipriani’s wife, a Brazilian actress named Greice Santo, told him that the Canadian billionaire Daryl Katz had propositioned her for paid sex, he pursued a sweeping campaign that ranged from suing Katz’s crisis PR adviser to outing Katz’s business partner, the producer Joel Silver, for employing convicted-felon PI Anthony Pellicano.
Santo is an executive producer on Star Serenade. The show’s original Spanish-language format, Serenata De Las Estrellas, has aired on Roku. Latin acts like Los Lobos and Ozomatli perform surprise sets of their hits for fans who’ve gone through hard times. “The show is very R.J., in that it’s about passion and perseverance,” explains the Grammy-winning music producer and engineer Humberto Gatica, who’s consulted on Serenata.
Cipriani expresses regret that his Hollywood quarrels have hurt his wife’s career: “When you want to hire her, you think, ‘Wait a minute, her husband’s that guy?'” He adds that he’s glad he doesn’t have kids because he’d be worried about repercussions for them. “They’d always be a target,” he says.
Cipriani expected that some well-known industry players would go on the record in support of him to THR. But they won’t talk, since his total war now includes newly named defendants David and Larry Ellison, while President Donald Trump is cited in his amended complaint as privately ensuring Paramount would win Warner Bros. Discovery over Netflix.
“One agent suddenly has jury duty,” he says, marveling. “A producer just had someone die on him. These people are scared.” He pauses. “It’s isolating.” One noted Hollywood figure finally did speak up, albeit anonymously: “All I can say is that R.J. has zero fear. Whether that’s good or bad, I don’t know. He’s not a guy to be worn down. He believes he’s on a righteous path, barrels forward, and doesn’t worry about the consequences.”
***
“There’s nobody that goes through shit — that’s lived a life — that hasn’t been arrested for something,” Cipriani says. “It’s just impossible.” Photographed by Daniel Prakopcyk This is Cipriani’s second collision with Shell. In 2023, he tipped off the media that then-CNBC anchor Hadley Gamble had filed an internal sexual harassment complaint against the executive. Shell was terminated from his position as NBCUniversal CEO, following an outside investigation.
The reason Cipriani moved against Shell the first time remains a matter of speculation. He’s known to be close with Ron Meyer, a fellow noted gambler whom Shell had earlier fired as vice chair at NBCUniversal over his undisclosed affair with actress Charlotte Kirk, who allegedly attempted to extort him. (Meyer paid her a settlement without informing the company.)
Cipriani claims he acted independently, without Meyer’s knowledge. “I did it just because that’s what I do,” he insists. Meyer tells THR: “I’ve never asked anybody to intervene on my behalf, and the thought that someone has is embarrassing.”
In the current dispute, Shell’s attorney Steve Olson has asserted in court that Meyer made multiple phone calls to his client, attempting to act as a backchannel intermediary for Cipriani while warning that Cipriani was a “bad guy” who could “make lots of trouble” if Shell didn’t acquiesce. Not long afterward, the word was out about Shell’s alleged breach of insider information on the Paramount-UFC media rights deal. (Cipriani has since publicized that he’s shared his evidence with Paramount’s outside investigators at the law firm Gibson Dunn.)
Meyer responds, “Jeff Shell has greatly distorted the facts, starting with: He reached out to me, I never reached out to him. In addition, the other claims are misrepresentations and false. I’ve called Steve Olson, his lawyer who I have great respect for, and told him that.”
Patty Glaser happened to represent both Shell and Cipriani. She had privately brokered peace between her clients after Shell lost his NBCUniversal job. Now, they’re both upset with her.
By Cipriani’s account, after meeting face-to-face in August 2024 with Shell at Glaser’s Century City office, he had a change of heart about the executive and spent the next 18 months quietly assisting his industry resurrection, mainly via his penchant for tactical leaks — all unpaid. This included, in his estimation, securing Paramount $1.5 billion in lower costs by leaking information about in-progress South Park contract negotiations to the press, including THR, in June 2025. (His $150 million in requested damages is “10 percent of what I saved them.”) Later, when Shell expressed appreciation, Cipriani pitched Star Serenade, initially over the phone — presuming the executive would, at the least, boost its chance for an inside track at a green light. That never happened.
“He strung me along,” Cipriani says. “He said to me, ‘R.J., I love you, if there’s anything I can ever do to repay you, please let me know.’ Then I brought up Star Serenade.” Cipriani asserts that Shell initially took the idea seriously, even suggesting how to navigate Paramount’s development process, but in the end, “We didn’t even have the first meeting.” Cipriani continues, “What he did was an oral contract.”
Larry Mullin, a veteran gaming industry executive who’s found himself enforcing casino bans on Cipriani, observes that “R.J. is a downhill runner” who’s “very aggressive, very competitive,” and “if you cross him, he takes it personally. Sometimes, too personally.”
For his part, Shell argues that Cipriani acted in his self-deputized communications strategist role without his authority — and it’s now clear to him, it’s an elaborate shakedown. In a filing, his attorney writes, “Cipriani’s playbook works like this: use a trusted mutual connection to cozy up to a high-profile target; leech to the fringes of the target’s world while manufacturing the illusion of closeness; falsely claim you have been helping the target from behind the scenes; then strike — demand compensation for your unsolicited efforts and, if not paid, weaponize that fiction, and the added threat of public exposure of equally false and salacious lies, to extract a massive payday.”
Cipriani considers this. “I’m a smart-enough guy from the streets of Philly and I knew how to ingratiate myself with someone,” he says. “I’m very sure of myself and my qualifications. I thought I could dazzle him. I always hoped he’d recognize my value. I did it on spec. I manifested it. I do that a lot. When I sit at the blackjack table, I think, ‘How much do I want to take out of that rack today?’ $200,000. OK, so I do that. I was gambling here with what I could do for the president of Paramount.” He adds, “It might sound strange, but that’s how I live my life — manifesting.”
That’s R.J. Cipriani, a man whose self-belief is rooted in upturning the adage about the house always winning. He appears intent to call every bluff and raise every stake. “Very few people,” he explains, “have the balls to bet big.”
This story appears in the April 8 issue of The Hollywood Reporter magazine. Click here to subscribe.
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