Ray J is doubling down on his assertion that Kim Kardashian and Kris Jenner have engaged in racketeering, saying in a new court filing that their family business empire is “a criminal enterprise akin to the mob.”

The Friday (Dec. 12) filing is the latest salvo in a salacious legal battle that began with Kardashian and Jenner suing Ray J for defamation after they say he falsely talked about them being investigated for racketeering on both a TMZ broadcast and Twitch livestream. The R&B singer countersued, accusing Kardashian of intentionally leaking their infamous sex tape back in 2007.

Ray J (William Ray Norwood Jr.) is now asking a Los Angeles judge to throw out the defamation allegations under California’s anti-SLAPP law, which bars meritless litigation that tramples on free speech. The singer says the claims will fail because, at the time he went on TMZ and Twitch, he genuinely believed Kardashian and Jenner had violated the Racketeer Influence and Corrupt Organizations (RICO) Act.

“To me, Kim and Kris have repeatedly engaged in a criminal enterprise and racketeering activity, violating RICO over and over again. I have no doubt about that,” writes Ray J in his Friday declaration. “Every time someone does something the Kardashians don’t like, they use their money and power to silence them. The Kardashian enterprise has made billions of dollars off their racketeering activities.”

Ray J’s filing then makes a very 2025 assertion: that his beliefs about the Kardashian family’s supposed racketeering activity were confirmed by ChatGPT. He says that when prompted with his claims against the family — including that they lied about the 2007 sex tape and extorted him into signing a fraudulent settlement agreement — the AI chatbot responded that he had a “strong” case for RICO.

This unusual argument is a creative one for clearing the “actual malice” threshold of libel law, in which a plaintiff must show that their defamer lied on purpose. AI chatbots like ChatGPT have often been criticized for being overly sycophantic, meaning they tend to echo back what you tell them. This can have the effect of entrenching false beliefs, which could theoretically make someone like Ray J believe they were telling the truth, even if a statement was actually specious.

Ray J’s Friday court filing also argues that regardless of whether he really believed what he said on TMZ and Twitch, the defamation claims should be thrown out because the broadcasts were not intended to be “taken seriously or at face value.”

“Norwood is also widely known as a successful ‘troll’ — a person who engages in provocation, insults people and talks a lot of ‘smack’ online,” writes his attorney, Howard King, in the anti-SLAPP motion. “‘Trolling’ is not slander; rather, it is a skill that streamers (like Norwood) wield to generate public discourse and create chaos which, in turn, increases viewership, online following, popularity and influence.”

Reps for Kardashian and Jenner did not immediately return a request for comment on Monday (Dec. 15). Their lawyer, Alex Spiro, has previously written in court filings that Ray J’s RICO claims are “blatantly false” and aimed merely at “reviving his own fading notoriety.”