Legal

With the Diddy trial now in recess for the long holiday weekend, Billboard is recapping the biggest moments over the first two weeks — from Cassie Ventura’s bombshell testimony about “freak offs” to a hunt for Suge Knight to Kid Cudi’s torched Porsche.

The trial, which is expected to last six more weeks, will decide the fate of Sean “Diddy” Combs, who federal prosecutors say coerced Ventura and other women to partake in the freak offs — drug-fueled sex with male escorts for his entertainment. His attorneys say the events were entirely consensual.

After just two weeks of testimony, there’s no shortage of big moments. Here are the six you — and the jurors — are going to remember.

The Video

On the very first day of the trial, prosecutors wasted no time getting to their most explosive piece of evidence: a headline-grabbing surveillance video of Combs beating Ventura in the hallway at Los Angeles’ Intercontinental Hotel in March 2016.

Ahead of the trial, the two sides spent months arguing over whether the clip could be played for the jury. Combs’ team argued first that it had been unfairly leaked to the press to taint the jury pool, and later said it had been deceptively edited and would confuse jurors. But prosecutors said he was merely “desperate” to hide “some of the most damning evidence of his sex trafficking,” and a judge eventually ruled that it could be played.

Prosecutors did so immediately, calling as their very first witness a former security guard at the hotel who responded to the incident. Playing with no audio in a silent courtroom, jurors looked on impassively as the ugly footage played twice, once with the security guard describing each moment in detail from the witness stand.

Graphic Details About Freak-Offs

Freak offs — elaborate events in which Combs allegedly forced Ventura and others to have sex with escorts while he masturbated — have been at the center of the case since it was filed. But on the first day of the trial, jurors got far more vivid details.

Daniel Philips, a male exotic dancer who said he’d taken part in numerous freak offs, described arriving to dark Manhattan hotel rooms, where he would have sex with Ventura at Diddy’s direction. When a prosecutor asked what Combs had been doing during the events, Philips didn’t mince words: “He was sitting in the corner masturbating.”

Philips’ testimony got darker and more graphic from there, describing ejaculation, urination, drug use and finally an outburst of physical violence against Cassie: “I was shocked. It came out of nowhere. I was terrified,” Philips said.

Later, Cassie told jurors her own side of the story, saying the parties left her feeling “humiliated” and eventually “became a job,” but that she felt she had no choice but to participate — first out of wanting to please a man she loved, and later out of fear of blackmail videos and physical violence.

When asked about whether she had wanted to be urinated on, Cassie was unequivocal: “No, I did not want it,” she said. “It was disgusting, it was too much. I choked. No one could think I wanted it.”

Celebrity Name Drops

The first two weeks of the Diddy trial have seen a number of major celebrity name-drops — none accused of any wrongdoing, but likely still to the chagrin of their publicists.

Under cross-examination, Ventura told the jury about a 21st birthday party that Combs threw for her at a Las Vegas club in 2007 — a key early moment in their romantic relationship. When asked about other celebrities in attendance, she said that Diddy had “brought Britney Spears” to the event. Later, defense attorneys mentioned Michael B. Jordan, suggesting Combs was jealous because he was suspicious Ventura was having an affair with the actor in 2015.

Then at the start of the second week, Danity Kane singer Dawn Richard told jurors that Combs once punched Ventura in the stomach at a Los Angeles restaurant where Usher and other celebrities were present. Richard’s testimony left it unclear whether the A-listers had actually seen the incident or merely been at the event.

The Hunt For Suge Knight

But no celebrity name drop was more dramatic than that of Suge Knight — the former CEO of Death Row Records and a major Diddy rival in the East Coast–West Coast hip-hop rivalry of the 1990s.

During her testimony last week, Cassie told jurors of a 2008 incident in which Combs abruptly left a freak-off after learning that Knight was at a diner nearby. “I was crying,” she said. “I was screaming, ‘Please don’t do anything stupid’.”

Then on Tuesday, Diddy’s former personal assistant David James offered another, more detailed perspective on the incident — saying he driven a black SUV carrying Combs, a security guard and multiple handguns to the restaurant, but that Knight had already left when they arrived. “It was the first time I realized my life was in danger,” James said.

Cassie’s Settlements

During cross-examination, Diddy’s lawyers got Cassie to reveal the size of two major civil settlements stemming from the abuse she allegedly suffered — a tactic likely aimed at making jurors question her motives for speaking out against Combs.

It was Ventura’s civil lawsuit, filed in November 2023, that first raised allegations against Combs. Though it sparked a flood of additional cases and set into motion the criminal probe that led to his indictment, the case itself was almost immediately dismissed after Cassie reached a private settlement.

At trial this week, Cassie confirmed that she had she had received $20 million in that deal. Diddy’s defense attorney quickly noted that Ventura had canceled an upcoming concert tour soon after inking that settlement. “As soon as you saw that you were going to get the $20 million, you canceled the tour because you didn’t need it anymore, right?” Estevao asked Ventura. “That wasn’t the reason why,” she replied.

Later that same day, Ventura said she would give the money back if she could reverse Combs’ abuse. “If I never had to have freak-offs I would have agency and autonomy,” Ventura said.

Near the very end of her testimony, Ventura also revealed another settlement for the first time, disclosing that she was expecting to receive roughly $10 million from InterContinental Hotels over the 2016 incident captured in the surveillance tape.

Kid Cudi Takes The Stand

Beyond Cassie herself, the highest-profile witness to testify so far has been Kid Cudi — a critically acclaimed rapper who briefly dated Ventura in 2011.

Cudi has long been linked to the case. Back when Ventura first sued, she suggested that Combs had blown up Cudi’s car as an act of jealous revenge. A spokesperson for the rapper later confirmed her account to the New York Times: “This is all true.”

Sitting on the witness stand, Cudi said it himself — telling jurors that he believes Combs broke into his Los Angeles house and later torched his Porsche with a Molotov cocktail. Shown a photo of his burnt-up luxury car, Cudi said, “It looks like the top of my Porsche was cut open, and that’s where the Molotov cocktail was put in.”

Cudi later told jurors that Combs had promised him he wasn’t responsible for the car explosion, but he said he believed Combs was lying.