Last year, Cipriani participated in an Amazon documentary about Owen Hanson, the former USC football player who became a drug kingpin, noting his involvement as an informant in the federal investigation into the case. (Cipriani was laundering money for Hanson, a role that he says he reported to authorities as soon as he understood that he was performing it. He has previously been convicted for insurance fraud and misdemeanor disorderly conduct.) It was perhaps his most high-profile brush with mainstream visibility, but as Shell noted in his complaint, Cipriani’s current foray into corporate intrigue has parallels with a 2017 episode. That year, Cipriani claimed in a defamation lawsuit against a crisis communications firm representing Canadian billionaire Daryl Katz that Katz had “inappropriately pursued [Cipriani’s] wife,” Brazilian model and actor Greice Santo, that his wife’s suitors, “all of whom accepted no for an answer,” included Leonardo DiCaprio, Axl Rose, John Stamos, and Jim Carrey. (The firm had accused Cipriani of attempting to extort Katz; a judge dismissed Cipriani’s suit.)
“Cipriani’s playbook works like this,” Shell’s lawsuit claims. “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.”
When I asked how he came upon the information he claimed to have released about Shell, Cipriani invoked an ambient proximity to a range of power players. “When you’re the high roller and you’re betting millions of dollars,” he said, “other people want to know you, want to be around you.” In 2005, he toured Vanity Fair’s Mark Seal through an ultra-private VIP casino, saying, “Sometimes the only people in the place were me, Tiger Woods, and Michael Jordan.” When I asked him for further examples of these high-level ties, he recounted a phone call with Michael Jackson that stemmed from his friendship with the singer’s brother Randy. “I actually sang a Michael Jackson song to Michael Jackson,” Cipriani boasted, “because I could sing really, really, really well.” I was unable to corroborate this call with Jackson, who died in 2009, or to verify Cipriani’s musical talents—when we spoke, he said he didn’t want to wake his sleeping wife.
In some sense, Cipriani has been rewarded for his persistence. As he relayed it, his entanglement with Shell began because he was “continuing to put bad stuff out about him in the news.” (Cipriani had been maintaining his campaign of innuendo against Shell on X, suggesting that further claims of sexual misconduct were forthcoming.) When Glaser asked him to stop, he said, he made a meeting with Shell a condition of any detente. (Glaser declined to comment.) Shell was contrite about his shortcomings, Cipriani said, so he decided to undertake unsolicited crisis communications on Shell’s behalf. (He claims that he placed a Hollywood Reporter story last year that favorably shifted the public narrative about a contract fight between Paramount and South Park’s creators. The magazine didn’t return a request for comment.) Shell was grateful, according to Cipriani, but not grateful enough—the gambler still hasn’t gotten his TV show.
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