Cassie Feared Blackmail Over Diddy’s ‘Freak Off’ Parties
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Casandra “Cassie” Ventura arrived to take the stand in her ex Sean “Diddy” Combs’s Manhattan sex-trafficking trial on Tuesday. Currently in the third trimester of her pregnancy, Cassie took the stand to describe Diddy’s “Freak Offs” and her alleged abuse at his hands. “He would mash in my head, knock me over, drag me, kick me — stomp me in the head if I was down,” Cassie said of the physical abuse. She testified that she loved Diddy but was frightened of the Freak Offs. “I just remember my stomach falling to my butt, just the nervousness and confusion in that moment,” she said. Here’s what to know.
What did Cassie say on the stand?
Sean “Diddy” Combs kept his eyes trained on ex Casandra “Cassie” Ventura as she walked to the witness stand in his Manhattan Federal Court sex-trafficking trial just after 11 a.m.
Cassie, sporting a long-sleeved, high-necked mocha-colored maxi dress with suede boots, did not look in Diddy’s direction while passing by — nor as she testified about a decade of alleged abuse.
“We were in a relationship a little over ten years,” Cassie said, leaning toward the mic. When arguments turned violent, she said, Diddy would get physical.
“He would mash in my head, knock me over, drag me, kick me — stomp me in the head if I was down.”
“How frequently?” prosecutor Emily Johnson asked.
“Too frequently.”
She’d have knots on her head. Swollen eyes. “Bruises all over my body.”
What happened when the prosecution showed the video of Diddy beating Cassie to the jury?
When Johnson displayed a still from this video on a screen in the courtroom, Cassie grabbed a tissue. “We were having an encounter … it was called a ‘Freak Off,’” she said. These parties started in the first year of their relationship — when she was in her early 20s and a self-described naïf. “Sean proposed to me this idea … called voyeurism; he would watch me in sexual activity with another person, specifically another male.”
“It just involved Sean being able to watch me with the other person.” Cassie said she was done with Freak Offs pretty quickly. “I knew it wasn’t something I wanted to be doing as regularly as it became,” she said. “I was just trying to make him happy.” As time went on, Cassie’s participation was motivated by fear. Diddy had recorded these encounters — and could blackmail her at any time. “It was always in the back of my mind.”
She described being stuck in Diddy’s web despite disliking these encounters. “Sean is a really polarizing person — also very charming. It’s hard to be able to describe in the moment.” A few moments later, as Johnson asked Cassie to describe aspects of her life before getting involved with Diddy, she dabbed her eyes with the tissue several times. Diddy’s daughters sat through this testimony, looking forward.
“I wanted to be around Sean for the same reasons as everyone else,” Cassie recalled of her early involvement with Diddy. He “was just this exciting, entertaining, funny guy who also happened to hold my career in his hands.”
What allegedly went down during Cassie and Diddy’s relationship?
Cassie, 38, prompted the onslaught of allegations against Diddy — which culminated in his arrest last September — in a bombshell November 2023 lawsuit in which she alleged that the music mogul coerced her into having sex with male escorts while he watched. Diddy settled Cassie’s shock lawsuit just one day after she sued him.
Federal prosecutors contend that Combs’s sexual demands were part of a “criminal enterprise” that abused women with violence, often through so-called “Freak Offs.” Combs allegedly forced women to partake in Freak Offs, which authorities describe as “elaborate and produced sex performances” with male escorts that Combs arranged, directed, masturbated during, and often electronically recorded.” Freak Offs were fueled by drugs, including molly, so that Diddy’s victims could continue participating despite physical exhaustion.
Early on in their relationship, around 2007, Combs made it Cassie’s job to “find and book escorts for Freak Offs,” prosecutor Emily Johnson said during her opening on Monday. “Freak Offs that were happening as often as once a week for days at a time. Meaning that for almost half of every week, Cassie was in a dark hotel room, high and awake for days, performing sex acts that she did not want to do on male escorts,” Johnson told jurors.
A key piece of prosecution evidence against Diddy is video of him beating Cassie in a Los Angeles hotel hallway about nine years ago. Cassie was trying to leave a Freak Off when Diddy followed her out of the room and “brutally” beat her. The video — part of which was first published by CNN in spring 2024 and was played in court — which takes place near an elevator at the Intercontinental Hotel, shows Diddy repeatedly kicking Cassie.
How has Cassie come up in the trial so far?
Before Cassie testified, prosecutors called two other witnesses whose testimony bolsters her allegations: the first, a present-day LAPD officer who worked hotel security during the 2016 attack, and the second, a onetime manager of a male strip club. Officer Israel Florez described receiving a call to the sixth floor “saying there was a woman in distress.” When Florez arrived to the sixth floor, he saw a male and female in the elevator lobby — and recognized Diddy. “I [saw] Mr. Combs in a towel and some, like, colored socks, sitting down to my— farther away from me on my right side. And I seen Ms. Cassie in the corner kind of like covering her face and bundled up in the corner,” he said. The woman “was in the corner. She was— she had her hoodie on. She was pretty much just covered up. I couldn’t see her face and she was just, you know, just pretty much in the corner.” A vase in the elevator area was “destroyed” on the floor. The woman “just said that she wanted her phone and her bag and she wanted to leave.” He escorted them back to the room, positioning himself in the doorway to monitor the situation, while she got her things. On the way back to the room, “He did tell her at one point that— he said you’re not going to leave.” She eventually left the hotel in a black SUV.
Following Florez’s testimony, Daniel Phillip, the former manager of a male strip club, took the stand. Around late 2012 or early 2013, Phillip’s boss asked him if he could do a bachelorette party at the Gramercy Park Hotel saying they had requested a Black male dancer, but all the other candidates were off. Phillip went to what he thought was a bachelorette party only to find that he was alone with Cassie and Diddy. She said her husband wanted to do something special for her. “She asked me if I would mind rubbing baby oil on her and giving her a massage and, um, you know, wherever things went from there, if it went, if, you know, based on how comfortable I was.” Cassie paid him several thousand dollars. Phillip and Cassie wound up having sex while Diddy masturbated in the corner. Over the course of a year, they would have numerous such encounters. Phillip told jurors that Diddy abused Cassie. He recalled seeing Diddy grab Cassie by the hair and dragging her into the bedroom. “I could hear him — what I could hear what sound like him — slapping her. She was screaming ‘I’m sorry! I’m sorry!’”
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