Singer Casandra “Cassie” Ventura, a former girlfriend of Sean “Diddy” Combs and a key witness in the federal sex-trafficking and racketeering trial of the music mogul, returned to the stand on Thursday for cross-examination.
One of Combs’s lawyers, Anna Estevao, opened her cross-examination of Ventura by asking: “You and Sean Combs were in love for 11 years, right?”
“Yeah,” Ventura said.
During the first few hours of cross-examination, Combs stared at Ventura as she answered questions. His sons and mother were present in the courtroom, as well as his publicist. Ventura’s husband was also present.
As Ventura entered the courtroom, she did not look at Combs and had not looked at him yet as of Thursday’s lunch break. She has been looking directly forward or to her screen showing the exhibits.
The defense team spent the first half-hour of their cross-examination establishing the trust and love that was once between Ventura and Combs.
“He was charismatic – big personality, larger than life,” Ventura testified. “The beginning of the relationship was really fast, fast-paced, scary. But the more time I spent with him, his real personality came out – sweet, attentive.”
Then the defense asked about the “freak-offs”.
“So, to make him happy you told him that you wanted to do ‘freak-offs’, right?” Estevao asked.
“No, there’s a lot more to that,” Ventura said.
The defense cited messages, via text and emails, between Combs and Ventura, to depict their relationship to the jury.
“In order for me to be more open with the things we do in bed, I need to feel safe, like home … like this is my husband, and this is the only man that will ever have this aggressive sexual side of me,” Ventura wrote to Combs in an email shown in court. “When we used to freak off when we were so in love there were no questions asked, it felt right. Like it literally made sense for the next step in our sex life together.”
Ventura later told the defense that the “freak-offs” were “an integral part” of her relationship with Combs.
In another message shown, Ventura told Combs she “never felt so loved, safe, and empowered since we’ve come together” but that “on the other hand, your [sic] constantly weary of me … ”
Ventura commented on that message that “it was usually, like, a one-way street when it came to messages like this”.
Other messages between Combs and Ventura that were shared were much more graphic and detailed, depicting both former partners’ various desires.
Combs’s lawyer then pivoted to the lawsuit Ventura filed in 2023.
“When your lawsuit was publicized in November 2023, you understood that his career was ruined at that point, right?” Estevao asked.
“I could understand that, yeah,” Ventura said.
She also told the court that she took ecstasy, or MDMA, to “be high during the ‘freak-offs’” and said that for points of their relationship, she and Combs were both addicted to opiates.
At times during the cross-examination, Combs was seen nodding his head and whispering to his lawyers. He would sometimes turn around to look at who was in the courtroom.
Just before the lunch break ended, Judge Arun Subramanian reminded the defense they would have to conclude their cross-examination by tomorrow as Ventura is heavily pregnant. Combs’s attorney Marc Agnifilo said that Ventura should be able to come back on Monday if necessary, prompting Subramanian to say: “In what universe did you not understand this is what was going to happen … You’re not telling me this was everyone’s understanding that this witness was going to be done this week?”
Ventura was in a side room during that exchange. Upon her return from break, she was then asked again about messages between her and Combs, specifically ones that suggest Ventura enjoyed the freak-offs.
“I would say that loving ‘FOs’ were just words at that point,” she testified.
In one exchange referenced in court, Combs said he wanted to have “an FO right now”, and Ventura replied, “lol me too,” adding: “Well I want to have fun with you.”
After more back and forth with the defense attorneys about freak-offs and how they were discussed, Ventura was asked about her feelings on Combs’s other former partner, Kim Porter, who died in 2018.
“I had some jealousy of Ms Porter,” Ventura said.
A 2013 message from Ventura to Combs was also shown to the court, which depicted Ventura’s jealousy that Combs, Porter and his children spent family trips together.
From there, the defense parsed through the mutual jealousy Ventura felt about finding out that Combs had other partners and how Combs felt when Ventura was dating other people, including Kid Cudi and actor Michael B Jordan.
“It seemed hypocritical to you that he would date other women,” Combs’s lawyer said, noting that Ventura wanted monogamy and acknowledging that Combs could be “far more jealous”.
“He had a bad temper and he reacted poorly to information that he didn’t like,” the lawyer said, which Ventura agreed to.
On how Ventura felt when Combs had suspicion that she was seeing someone else, she testified: “It was a little scary.”
On Ventura’s second day of testimony on Wednesday, she provided more details about the physical and psychological abuse she alleged she experienced from Combs during their on-and-off again relationship that lasted about 11 years, and accused the music mogul of rape and blackmail.
At one point on the stand, Ventura broke down in tears as she testified that Combs raped her in 2018 at her home after they had broken up.
The alleged rape was first mentioned in 2023 when Ventura filed a civil lawsuit against Combs. The lawsuit accused him of physical and sexual abuse. Combs has denied the allegations.
The two reached a settlement in one day. On Wednesday, Ventura revealed she received $20m from Combs and his companies in the settlement.
The lawsuit prompted the federal investigation that led to Combs’s arrest in September last year.
Combs is facing charges including racketeering conspiracy, sex trafficking and transportation to engage in prostitution. He has pleaded not guilty and denies all allegations. If convicted, Combs, who has been jailed since his arrest last year, could spend the rest of his life in prison.
In the final hour of testimony on Wednesday, prosecutors asked Ventura why she decided to testify against Combs.
“I can’t carry this any more,” Ventura said. “I can’t carry the shame, the guilt, the way I was guided to treat people like they were disposable. What’s right is right, what’s wrong is wrong. I am here to do the right thing.”
The defense’s cross-examination of Ventura is expected to stretch into Friday.
