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Diddy’s Best Bet: Prove Cassie and Jane Consented to the ‘Freak Offs’


Sean “Diddy” Combs is building a “consensual sex” defense — and ex-prosecutors say that while that may be a long shot, it’s also his best shot.

“What the defense is trying to do is show that these were consensual, boyfriend-girlfriend situations,” former prosecutor Michael Bachner told Business Insider.

“And they’re trying to show that these were situations that then went awry,” said Bachner, speaking of Combs and his two sex-trafficking accusers.

Prosecutors may rest, and the defense may start calling witnesses as early as this week in Combs’ trial in federal court in Manhattan.

Throughout a month of testimony by prosecution witnesses, the government has done a good job of proving the individual elements of sex trafficking, Bachner and other former prosecutors say.

They’ve shown that R&B artist Cassie Ventura and a second ex-girlfriend, “Jane,” were transported across state lines for commercial sex acts, the former prosecutors said. These were the dayslong, drug-fueled performances with male sex workers — Ventura called them “freak offs,” and Jane, a pseudonym, called them “hotel nights” — at the center of the trial.

Prosecutors have also presented strong evidence that force, fraud, and coercion were all in play in these two relationships.

Both women have described vicious beatings at Combs’ hands, accounts strengthened by photographs of their bruises and eyewitness corroboration. Jurors have also seen years of emails and text messages in which the women tell Combs of their anguish over his violence and broken promises.

But the federal law requires sex trafficking through force, fraud, or coercion.

Prosecutors must show that these were linked. And if at least one juror questions this link — if they find that Ventura and Jane engaged in years of freak offs or hotel nights willingly, and not because Combs made them — then the trial could end in a mistrial or acquittal on the sex-trafficking counts.

That’s why the defense has worked so hard to blur the link between freak offs, or hotel nights, and the violence and betrayal that also permeated these relationships, the former prosecutors said.

“They’re trying to show Combs had sexual desires and sexual interests and sexual curiosities,” said Bachner, who was on the defense team when Combs was acquitted of gun possession and bribery in state court in Manhattan in 2001.

“And the women were more than willing to fulfill those desires and those inquiries, so long as they felt that they were being properly compensated,” both financially and emotionally, Bachner said.

Throughout the years that these freak offs and hotel nights were happening — between 2009 and 2018 for Ventura, and between 2021 and 2024 for Jane — both women exchanged explicit texts with Combs in which they professed, at times, to show their enjoyment of these sexual marathons, according to trial evidence.


This sketch by a courtroom artist shows Cassie Ventura testifying at Sean

Cassie Ventura testified during the first week of Sean “Diddy” Combs sex-trafficking and racketeering trial.

Jane Rosenberg/REUTERS



These texts show their apparent humiliation and regret over these marathons. On the witness stand, both women testified that they only pretended to enjoy themselves at the time due to Combs’ violence and their emotional and financial dependence on him.

But both women say they broke up with Combs repeatedly during these relationships — often after seeing him in social media posts dating other women — only to return after he promised to treat them better.

“Even after the abuse, they’re still coming back to Diddy,” said Mark Chutkow, an attorney at the law firm Dykema and a former federal prosecutor in Michigan who has prosecuted cases involving organized crime and sex trafficking.

“They’re trying to plant the seed in the mind of the jurors, well, if he really is this monster, and they’re out there back in the real world amongst everyone else, why would they be drawn back?” Chutkow said of the defense.

It’s a diametrically opposite worldview to that presented by federal prosecutors and their sexual abuse expert, who took the stand last month and described the complex trauma bond that keeps victims returning to their abusers.

Combs “very much wants to show that these relationships, while undoubtedly toxic and violent, were consensual, and that the sex that went along with them was the same,” said Sarah Krissoff, a former federal prosecutor in Manhattan.

“This was a challenging case for the prosecution,” Krissoff told BI.

“The allegations span an enormous timeframe, and they are telling a whole bunch of stories within one trial,” she said. “Their witnesses are clearly very well-prepared, and the government has anticipated many of the defense arguments. But the sprawling nature of the allegations makes this a tougher case than usual for the government.”

Still, jurors only need to find that Combs sex-trafficked Ventura or Jane through force on a single night in order to convict, experts said.

And both Ventura and Jane have testified about specific freak offs or hotel nights they described as steeped in violence.

Ventura described trying to leave a 2016 freak off at the InterContinental hotel in Los Angeles after Combs, she said, punched her in the eye. Jurors have repeatedly seen the security footage showing Combs kicking Ventura and dragging back toward the hotel room.

Jane, in her turn on the stand, described a June 2024 “hotel night” at the Los Angeles home Combs continues to pay the $10,000 rent on. She said Combs — already under investigation at that point for alleged sex trafficking — beat her brutally, then demanded she take an ecstasy pill, cover her bruises with makeup, and have sex with an porn actor named “Antoine.”

“You’re not going to ruin my fucking night,” Jane said Combs threatened.

Jurors have read contemporaneous text exchanges describing these two instances of violence, and they’ve seen photographic images of both women’s injuries.

“I’m sure the prosecution is going to argue yes, ladies and gentlemen, this was a complicated relationship,” Bachner said.

“And they’ll say let’s think of what wasn’t complicated — what wasn’t complicated is he beat her up to get sex.”





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