Cassie Ventura testifies about freak-offs, escorts in Sean Combs’ sex-trafficking case

Star witness Casandra “Cassie” Ventura returned to the stand Wednesday in the federal criminal trial of her former boyfriend, the massively influential music producer Sean “Diddy” Combs, who faces 15 years to life in prison if convicted.

Prosecutors allege Combs used drugs, violence and his power in the industry – he ran Bad Boy Records and was synonymous with the A-list party scene – to sexually abuse Ventura and others.

Combs, 55, has pleaded not guilty to all criminal counts of sex trafficking, racketeering conspiracy and transportation to engage in prostitution.

Ventura testified on Wednesday that videos of her from the freak-offs – days-long drug- and sex-fueled parties with male escorts, which Combs allegedly filmed and directed down to the smallest details – were used to “blackmail” her. She told the court that Combs would threaten to leak the videos – a prospect that horrified her.

“It’s horrible and disgusting. No one should do that to anyone,” Ventura testified.

Ventura also testified that Combs controlled every aspect of her life, including their sexual encounters. She walked jurors through January 2016 text messages between the couple. “You know we have to have a proper (freak-off) without no K … I hate K!!!!” Combs wrote in the exchange, an apparent reference to ketamine. Ventura told the jury the drug made her sexually inactive during freak-off sessions.

“It took me out of it for too long,” she said. “We’re just high and not doing any … intercourse.”

Ventura previously testified that Combs orchestrated every detail of these sex sessions, including the lighting in the room and what color her nails were.

On Tuesday in court, Ventura was shown photos of men alleged to have participated in “freak-offs” and asked to identify them by name, and to testify about how and where they were hired and in what cities they participated in the sex sessions.

On Wednesday, Ventura was being asked to do this again. The escorts are a racially diverse group of men, some of whom Ventura only remembered “vaguely.” She was unsure of some names. There were at least six men shown. Ventura said it was her “job” to hire these men – that it was “expected” of her by Combs. Ventura testified that she performed sex acts with all the men shown and that those who were paid were paid with “Sean’s money.”

Much of Ventura’s testimony has recounted the allegations she made against Combs in a 35-page lawsuit in November 2023 that first triggered his legal troubles. While on the stand, prosecutors asked her to review hotel footage from 2016, which shows Combs wearing a towel as he attacks her in a hallway.

After a lunch break on Wednesday, Prosecutor Emily Johnson handed Ventura a black binder and turned off the exhibit feed, indicating that the evidence presented to the jury was under seal.

Ventura was shown an image of “Mia,” an alleged victim who will be testifying under a pseudonym, and asked whether she is familiar with her. Ventura said she was. She next identified an image of Jules, a male escort she’s previously referenced in testimony. These images were from a freak-off, Ventura confirmed.

Ventura identified another image of herself and Jules at a different freak-off. These are still images from videos that were taken from Ventura’s personal devices.

Jurors did not have any notable facial expressions as they looked at the series of freak-off photos shown during Ventura’s testimony. Some looked at their screens briefly as each photo was shown and then switched their gazes to Ventura or the prosecutor. Others occasionally took a second or third look, or stared down at their screens – situated at lap level – for most of the time they were displayed. Jurors at big trials often remain dispassionate even while viewing disturbing court exhibits or hearing unsettling testimony.

During questioning, Ventura was asked about Kid Cudi, a rapper she mentioned in her 2023 lawsuit against Combs. She claimed Combs threatened to blow up Cudi’s car in a fit of jealousy. According to the lawsuit, Cudi’s car exploded in his driveway a short time later.

Ventura said she dated Cudi, whose legal name is Scott Mescudi, for a brief period in 2011 when her relationship with Sean Combs was on-and-off. Combs found out when he went through her phone during a freak-off in Los Angeles, Ventura said. He found an email between Ventura and one of Mescudi’s staffers that mentioned bringing Ventura’s toiletry bag to Mescudi’s home. Ventura said Combs put a wine bottle opener between his fingers and lunged at her, but she managed to escape.

Ventura broke off her relationship with Mescudi in 2011, she said. It had gotten to be “too much,” she told the court. “Too much danger, too much uncertainty.” She said she worried that Combs would hurt both of them.

Ventura was also asked by the government if she ever started a physical fight with Combs. Ventura said she did. Johnson followed up by asking if she had ever seen injuries on Combs as a result of a fight Ventura started. Ventura said she hadn’t.

Johnson then asked if Ventura was injured as a result of him becoming “physical.” She said she had been – “there would at least be a bruise.” These fights would require “days’ worth” of recovery, she said.

Ventura recounted once initiating a physical fight with Combs as they rode in a Cadillac Escalade in Los Angeles. She said she punched Combs in the face as hard as she could, after which his “whole demeanor” changed. “His eyes went black” and he began to attack her, Ventura said. She took shelter under the backseat of the Escalade, she said, and tried to cover her face as Combs stomped on it.

Ventura said the fight in the Escalade happened in front of an assistant and a “security driver” by the name of Roger Bonds. She said the aggression didn’t end until they arrived at Combs’ residence, at which point she ran out of the car. Bonds caught her and brought her into the home, she testified.

Inside, Ventura saw her face.“(I) didn’t look like myself at all. Just knots and bleeding. Swollen everything,” she told the court. She recalled that she was vomiting when Combs appeared, and his demeanor transformed once again. “The person he switched over to (during the car ride) was now gone,” Ventura said. Combs was “freaking out” over her injuries. She said he told her to sneak out of the house with security and hide out in a hotel. She checked into a room that night.

There were too many incidents of abuse during her 11-year relationship with Combs to recall them all, Ventura said, but she remembered that some of his staff were visibly upset by her treatment.

“When D-Roc saw me he started to cry,” Ventura said, referring to one of Combs’ regular security guards, as she recalled a beating that left her with “black eyes, golf ball-sized knot (on my) forehead, busted-up lip.”

As the trial goes on, prosecutors may ask some of Combs’ former employees to corroborate aspects of Ventura’s testimony.