Diddy Claims First Amendment Right to Film “Freak-Offs” in Legal Bid to Toss Conviction

In a stunning legal twist, Sean “Diddy” Combs is arguing that his sexually explicit “freak off” tapes — involving male escorts and degrading sessions with his lovers — are protected speech under the First Amendment.

Sean Diddy Combs, currently jailed and awaiting sentencing for violating federal prostitution laws, claims that his home-directed pornography qualifies as “creative expression” and is therefore constitutionally protected. The filing comes just weeks before Diddy faces up to 10 years in prison for orchestrating sex sessions that involved transporting escorts across state lines — a violation of the Mann Act.

“Mr. Combs’s amateur porn, like many other adult films, was creative, intricate, and highly choreographed,” wrote his attorney Alexandra Shapiro in a motion filed Wednesday night. “The expressive content of these tapes places them squarely under the protection of the First Amendment.”

The tapes — reportedly filmed with multiple partners, including male escorts — were a central piece of evidence during Sean Diddy Combs’ explosive two-month trial in Manhattan. One of the most damning accusations came from Cassie Ventura, Combs’ former girlfriend, who alleged he used threats of releasing the tapes to control and intimidate her.

“I feared for my career. I feared for my family,” Ventura testified. “It’s horrible and disgusting. No one should do that to anyone.”

Another woman, identified only as “Jane”, testified that Sean Diddy Combs beat her and then coerced her into a sex act with a hired escort. “Is this coercion?” Combs asked before ordering her to perform, according to her account. However, jurors acquitted him on coercion charges, with the defense presenting intimate messages from the women that complicated the prosecution’s narrative.

The jury ultimately convicted the 55-year-old on two prostitution-related charges but rejected broader sex trafficking and racketeering counts. During the trial, Sean Diddy Combs’ defense team admitted to the domestic violence, but denied that his actions met the legal standards for trafficking.

“Domestic violence is the issue. We own it,” defense lawyer Marc Agnifilo said in closing arguments.

Diddy’s team is now urging Judge Arun Subramanian to throw out the conviction ahead of the October 3 sentencing. While trial judges rarely overturn jury verdicts, the defense’s argument may lay the groundwork for an appeal to the 2nd Circuit Court of Appeals.

In the meantime, Sean Diddy Combs remains behind bars at a Brooklyn detention facility. Judge Subramanian cited the rapper’s admitted abuse and potential flight risk in denying his release.

As the October date nears, Sean Diddy Combs’, Freak offs, First Amendment claim could either be a long-shot legal gambit — or the first step in reshaping the limits of free speech in the age of celebrity scandal.