The explosive trial of music mogul Sean “Diddy” Combs took another harrowing turn this week as Casandra “Cassie” Ventura, his former longtime girlfriend, testified about years of alleged abuse, control, and humiliation during their 11-year relationship.
Ventura appeared in court on May 15, marking the fourth day of Combs’ sex-trafficking, racketeering, and prostitution trial, where she recounted disturbing details of the star’s private life, including forced participation in so-called “Freak Offs” — hours-long sex parties allegedly involving drugs, male sex workers, and videotaped encounters.
According to Ventura’s testimony, she endured these experiences to remain close to Combs, often dissociating under the influence of drugs to cope with the abuse.
At times, she feared the repercussions of resisting him.
Jurors were earlier shown the now-infamous video of Combs violently assaulting Ventura in a Los Angeles hotel lobby in 2016, an incident she says occurred when she attempted to leave one of those parties.
During cross-examination on Thursday, the court heard exchanges of text messages between the pair, with Ventura expressing frustration over being treated more like a participant in Combs’ fantasies than a valued partner.
In one revealing 2013 message, she criticized how Combs isolated her from his personal life — especially his children — and compared his behavior to other high-profile figures known for maintaining respectful relationships with their exes and blended families.
“As much as you think you’re Bruce Willis, you aren’t,” she wrote, referencing the actor’s famously amicable relationship with ex-wife Demi Moore and their ability to co-parent while nurturing new relationships.
Ventura highlighted how Willis and Moore prioritized family unity, even vacationing together post-divorce — something she longed for in her own relationship with Combs.
Another headline-making moment came when Ventura was questioned about whether Combs suspected her of being romantically involved with another celebrity.
Defense attorney Anna Estevao asked if Combs believed she was having an affair during the filming of Honey 3 in South Africa in 2016. Ventura confirmed that Combs suspected and accused her of dating actor Michael B. Jordan.
While Jordan, best known for roles in Creed and Black Panther, is not expected to testify, his name surfaced multiple times during jury selection.
Ventura testified that around the same time, she saw a photo of Combs with another woman, which sparked anger and deepened the emotional strain in their relationship.
The trial has peeled back the curtain on Ventura’s struggles — from private anguish to public confrontation.
Messages between Combs and Cassie — both romantic and lurid — were the focus of the fourth day of testimony in a Manhattan courtroom. Defense attorney Anna Estevao read what Combs wrote, while Cassie recited her own messages about what she wanted to do during the freak-offs.
In emails and texts read aloud in court, she expressed heartbreak over the way Combs treated her, lamenting his emotional neglect.
In a 2010 message, she wrote, “That’s not being in a relationship with someone that you love and are in love with … I don’t need your money, I need some attention.”
Ventura initially filed a civil lawsuit against Combs in 2023, settling for $20 million, but her testimony has now become central to a broader criminal case.
Lawyers for Combs sought to portray Cassie to the jury as a willing and eager participant in the music mogul’s sexual lifestyle.
Combs has pleaded not guilty to federal sex trafficking and racketeering charges. His defense says that, while he could be violent, nothing he did amounted to a criminal enterprise.
Prosecutors say he exploited his status as a powerful music executive to violently force Cassie and other women into these marathon encounters with sex workers, called “freak-offs,” which sometimes lasted days. Combs insists all the sex was consensual.
He’s also accused of using his entourage and employees to facilitate illegal activities, including prostitution-related transportation and coercion, which is a key element of the federal charges.
Combs, who has pleaded not guilty, faces charges of sex trafficking, racketeering, and transportation for prostitution. Since the lawsuit, the hip-hop mogul has further been bombarded with additional legal claims alleging sexual misconduct and violence.
Cassie and Diddy text message exchanges read in court
While Cassie, has said she felt compelled to participate in freak-offs to keep Combs happy, Estevao pointed to message exchanges where Cassie appeared excited about the sexual encounters and raised the idea of having one on her own.
In August 2009, Combs asked when she wanted the next encounter to be, and she replied “I’m always ready to freak off.”
Two days later, Cassie sent an explicit message and he replied in eager anticipation. She responded: “Me Too, I just want it to be uncontrollable.”
Later that year, however, she also sent Combs messages that she was frustrated with the state of their relationship and needed something more from him than sex.
Estevao also noted a July 2013 text message exchange where Cassie wrote to Combs, “Wish we could’ve FO’d before you left,” using the initials of freak-off.
In a 2017 text message, Cassie told Combs: “I love our FOs when we both want it.” On the stand Thursday, Cassie explained: “I would say loving FOs were just words at that point.”
Cassie complained at one point that jurors weren’t hearing the full context of the messages the defense was highlighting, saying, “There’s a lot we skipped over.”
Combs’ attorney presented Cassie with sexual texts she sent before a 2016 encounter at a Los Angeles hotel, where Combs was caught on surveillance video kicking and dragging her in a hallway.
Cassie said she wanted to get the encounter over with, in order to keep Combs happy and avoid a scene ahead of movie premiere she was attending days later.
Estevao raised instances of Cassie’s anger with Combs and her admitted jealousy over attention he gave other women. Cassie said Combs didn’t want her seeing anyone else, but the same rules didn’t apply to him.
As the explicit messages were read, Combs appeared relaxed at the defense table, sitting back with his hands folded and legs crossed.
The courtroom was packed with family and friends of Combs, journalists, and a row of spectator seats occupied by Cassie’s supporters including her husband.
During a break, Combs stood at the table, huddling with his lawyers, holding a pack of Post-It notes in one hand and a pen in the other. At one point, he turned to the gallery and acknowledged a few reporters who were studying his demeanor. “How you doing?” he asked.
Combs’ daughters were not in the courtroom Thursday.
Jurors leaned forward in their seats to follow along as the messages were displayed on monitors in front of them in the jury box. One woman shook her head as a particularly explicit message was shown. A man stared intently at the screen, pressing his thumb to his chin. Other jurors appeared curious and quizzical, some looking at Cassie or jotting notes.
The trial is set to continue on Friday.
