Sean ‘Diddy’ Combs Attacking Cassie in Trafficking Case Could Backfire

Throughout a failed, two-day bid to get Combs freed on bail before trial, Agnifilo described an alternate universe to the one outlined by federal prosecutors.

Prosecutors say Combs used violence and threats to force Ventura to engage with male sex workers in drug-filled, dayslong performances he staged throughout the past decade.

But “that is their thing,” Agnifilo argued in court of these so-called “Freak Offs.” “That is how these two adults chose to be intimate.”

In Combs’ version of the story, as described by his lawyer, Ventura is money-seeking, jealous, and unfaithful. She betrayed his generosity, running off and starting a family with the personal trainer he’d paid for, Agnifilo argued, then demanding $30 million from Combs to stay quiet.

“He and this person had a mutually toxic relationship,” Agnifilo argued Tuesday, with language that resembled courtroom descriptions of the relationship between Johnny Depp and Amber Heard, where Depp ultimately emerged victorious in civil litigation.

“Attack the accuser” is a risky strategy in any sex case, and especially so in this one, where key evidence — video of Combs admittedly beating Ventura in a hotel hallway — has already won her widespread public sympathy.

But as ugly as it is, going on the attack may be Combs’ only defense, former federal prosecutors told Business Insider.

And federal rules of evidence let him do it — at least to some extent.

“It is an aggressive approach,” said Ephraim Savitt, who has handled sex trafficking cases as both a federal prosecutor and defense attorney.

“But you can’t claim an alibi or mistaken identity, so the only defense is that she was a willing participant and ultimately tried to extort him, assuming there is any truth to that,” Savitt said. “I really think that Agniflo had no option but to be aggressive in showing that the proof being presented by the government as overwhelming is subject to attack.”

Combs has pleaded not guilty to the charges against him. Lawyers for Combs and Ventura have declined to comment on this story.

Evidence rules limit victim-blaming — but Diddy has an opening

Federal law sets strict limits on what defense lawyers can tell a jury about a victim’s sexual past.

Those limits are set down in a section of the federal evidence statute known as “Rule 412.” It bars defense lawyers from besmirching a victim by dragging up their sexual preferences and history.

But there’s an exception to Rule 412, one big enough for Combs to stake his defense on.

Federal judges will allow evidence of a victim’s sexual past and predilections “if offered by the defendant to prove consent,” the rule states.

Within the next few months — very likely as he continues to sit in a federal jail — Combs’ lawyers and prosecutors will begin a pitched battle over Rule 412, arguing over what evidence of Ventura’s sexual history and preferences — with Combs and others — may be shown to jurors.

US District Court Judge Andrew Carter will keep many of these dueling court fillings under seal over victim privacy concerns, experts predicted.

In battles over Rule 412, “the defendant may have a bit of an edge,” said Jennifer Beidel, a former federal prosecutor in Manhattan.

“If a judge excludes a defendant’s best evidence and there’s a conviction, then there’s a very easy appeal issue,” Beidel, a government investigations attorney at Dykema, said.

“In a lot of close-call scenarios, they may over-admit, so that there’s not this appeal issue,” she added.

The evidence already described publicly — including video of the “Freak Offs” themselves — is ugly enough. In his bail arguments this week, Agnifilo said the defense has interviewed some of the male escorts involved in these performances.

“I have asked all the questions I could think of,” he argued Tuesday. “Did anything ever, ever seem remotely nonconsensual? Was anybody too drunk? Was anybody too high? Did anyone express any hesitation? Was there the slightest inkling that possibly — possibly — the woman wasn’t consenting? No, no, no, no,” the lawyer said.

Agnifilo also mentioned a recorded conversation in which Ventura’s lawyer asked Combs’ lawyer for $30 million to keep the R&B star from publishing a tell-all book about the relationship.

Soon after, Ventura filed a civil lawsuit against Combs and his companies in November 2023, detailing the allegations against him. The case quickly settled for what Agnifilo described in court as “an undisclosed and large amount of money.”

Nonetheless, the lawsuit was quickly followed by a criminal investigation into Combs and a cascade of civil lawsuits accusing him and his companies of various misdeeds.

The previous civil lawsuits and interactions between Combs, Ventura, and other possible victims will give Agnifilo plenty of ammunition for cross-examination.

But ultimately, the case will come down to the weight of the evidence, said Elizabeth Geddes, a former federal prosecutor in Brooklyn who brought the racketeering and sex-trafficking case against R. Kelly.

Twelve accusers testified during the Kelly trial, several of whom had years-old civil lawsuits against the singer, including ones that reached “very lucrative private settlements,” Geddes said. Some accusers had also posted on social media about the abuse they suffered at his hands.

Kelly’s defense lawyers tried to poke holes in their stories, pointing out what they said were discrepancies between their civil lawsuits, social media posts, interviews with the FBI, and testimony on the witness stand.

In the end, the evidence against Kelly was overwhelming.

“We were able to overcome all of that by just showing how corroborated their testimony was, how genuine their testimony appeared,” Geddes said. “And obviously, the jury agreed.”

Attacking the accuser can backfire at trial

If a judge does allow Combs to air his blame-the-accuser defense, it may backfire before a jury.

“Blame the victim is a defense of last resort,” said Savitt, of the Ephraim Savitt Law Firm in Manhattan. “If the jury is sympathetic to her, and now you’re attacking her, then hatred for the defendant can start to boil up in the jury pretty easily.”

Ventura is also unlikely to be the only accuser to testify at the trial, according to Geddes, now an attorney at Shihata & Geddes LLP.

The indictment refers to multiple “victims” of Combs, and Geddes said their specific allegations may likely be described in under-seal evidence or future indictments.

“I’m very confident that they have multiple victims,” Geddes told BI.

Prosecutors have sought to show how Combs used the vast resources of his business empire — he owns companies in the music, fashion, and liquor industries — to facilitate his sex-trafficking, including by arranging flights for male escorts and having 1,000 bottles of baby oil and lubricant on hand. Prosecutors say Combs also relied on employees to cover up his misdeeds, suggesting they pressured hotel security to delete records of Combs assaulting Ventura.

“The reason why these men, in many ways, have been able to get with committing these alleged crimes is that they had the benefit of all of these people working for them and with them, and carrying out all of their whims,” Geddes said.

According to Geddes, structuring the case as a racketeering conspiracy will allow prosecutors to illustrate the “extraordinary power disparity” between Combs and victims, including Ventura, regardless of the particulars of their relationship. Combs’ wealth, status, and army of employees were weaponized to coerce his victims, prosecutors say.

“Even if he produces evidence that shows that Cassie or any of these victims said ‘Yes’ — that would not negate the government’s case here,” Geddes said. “Because that’s the very nature of the crime: that any consent was coerced.”

A big worry for prosecutors might be ensuring there aren’t any jurors who are awed by Combs’ fame.

“It only takes one person to hang a jury and refuse to convict,” said Geddes, who helped pick the jury for R. Kelly’s trial. “And it can be very hard to suss out who may be a closet Diddy fan.”