Sean 'Diddy' Combs trial updates: Cassie Ventura breaks down as testimony concludes

The hip-hop mogul is charged with sex trafficking and racketeering conspiracy.

Last Updated: May 19, 2025, 9:00 AM EDT

This story may contain accounts and descriptions of actual or alleged events that some readers may find disturbing.

Friday is day five in the trial of Sean Combs after the jury was seated.

May 13, 2025, 10:11 am

Sean Combs trial underway

The highly anticipated trial of hip-hop mogul Sean "Diddy" Combs is underway. Combs has been accused of sex trafficking by force, transportation to engage in prostitution, and racketeering conspiracy as part of a blockbuster federal indictment originally filed in September 2024. He later faced two additional superseding indictments. Combs has pleaded not guilty to all of the charges.

Combs is accused of being the ringleader of an alleged enterprise that "abused, threatened and coerced women" into prolonged, drug-fueled sexual orgies with male prostitutes, which he called "freak offs," and then threatened them into silence. Combs has said that all of the sex was consensual and that while his relationships sometimes involved domestic violence, he wasn't engaged in trafficking.

Combs' lawyer, Marc Agnifilo, said Combs was simply part of the swinger lifestyle and that he "vehemently denies the accusations made by the SDNY" and "looks forward to his day in court."

May 16, 2025, 2:37 PM EDT

Defense concludes their cross-examination of Cassie Ventura

The cross-examination of Cassie Ventura concluded with a 2012 text exchange in which Sean Combs asked Ventura if she wanted to "have a 'freak off' one last time."

Her response said she wanted to "'freak off" for "the first time for the rest of our lives"

Prosecutor Emily Johnson immediately showed the exchange on re-direct examination as part of a longer thread in which Ventura expressed different feelings about "freak offs."

The defense again attempted to portray Ventura as a willing, even eager, participant in the kind of sexual lifestyle Combs wanted.

The defense also asked Ventura about her Instagram post after CNN first aired the 2016 hotel surveillance video depicting Combs attacking her near an elevator.

"Domestic violence is the issue and it's an important issue," Ventura posted in part on May 23, 2024. "My only ask is that EVERYONE open your heart to believing victims the first time. It takes a lot of heart to tell the truth out of a situation that you were powerless in," the post continued.

"That's what you focused on in your Instagram post?" defense attorney Anna Estevao asked. "There was more to it but yeah," Ventura replied.

The defense has argued that Ventura may have been a victim of domestic violence, but she was not a victim of sex trafficking.

The defense has also argued Ventura is motivated by money and pointed out she canceled an Australian and New Zealand tour after settling her 2023 civil lawsuit.

"You saw you would get $20 million and you canceled," Estevao said. "That wasn't the reason why," Ventura testified.

May 16, 2025, 2:10 PM EDT

Cassie Ventura's husband exits courtroom during alleged rape testimony

Ventura’s husband, Alex Fine, who has been in the courtroom each day of her testimony, left during the portion of questioning about the alleged rape. Defense attorneys had suggested at the outset they may call him as a witness.

The jury’s interest appeared piqued by the discussion about the alleged rape and the defense attempts to cast doubt on Ventura’s account. During testimony on the recording of the conversation between Ventura and Sugit about a sex tape, jurors seemed interested. On the tape, Ventura spoke loudly or with anger. Based on her reaction, she seemed to be amused by her tone on the recording.

The cross-examination is set to resume momentarily following the lunch break.

May 16, 2025, 1:42 PM EDT

Defense digs into Ventura and Combs' 2018 breakup, rape allegation

The jury is seeing messages and hearing testimony about the prolonged breakup of Sean Combs and Cassie Ventura in late 2018, which the defense appears to be using to try and raise further doubt about her rape allegation.

"You don't say anything to the effect of, 'the last time we saw each other you raped me,'" Estevao noted about Ventura's communications with Combs.

According to Ventura's testimony, the last she and Combs had sex was Sept. 27, 2018, when Ventura testified she received a FaceTime call from her now-husband Alex Fine.

"Did you answer that call?" defense attorney Anna Estevao asked. "No," Ventura responded.

"Was it in the middle of sexual intercourse that you received this call?" Estevao asked. "We were together. I don't know," Ventura responded.

"Your husband learned about your evening with Mr. Combs, right?" Estevao asked. "You told your now-husband that Mr. Combs raped you."

"That wasn't the evening I was raped," Ventura testified. When Fine eventually found out about the alleged rape, Ventura testified that he punched a wall.

Earlier, the defense showed Ventura transcripts of her interviews with law enforcement agents, pointing out that she told them that the night of the alleged rape Combs was acting "nice but strangely." The defense also tried to point out how Ventura wondered whether the alleged attack occurred because of Combs potentially having bipolar disorder, the first time such a condition was mentioned at trial.

Combs discussed his mental health struggles in a 2009 Playboy Magazine article.

"I think therapy is good. I've been called bipolar - I'm not; I just have very drastic mood swings," he said in the interview.

The jurors are in a lunch break.

May 16, 2025, 12:42 PM EDT

Defense attempts to show Ventura's agency in 'freak offs,' relationship with Combs

The defense introduced scores of text messages during the cross-examination that contain a mix of affection, sexually-charged banter, domestic negotiation and bickering.

Casandra "Cassie" Ventura is cross examined by Lawyer Anna Estevao during Sean "Diddy" Combs' sex trafficking trial in New York City, May 16, 2025 in this courtroom sketch.
Jane Rosenberg/Reuters

The defense has attempted to demonstrate that those messages show Ventura’s agency in a relationship that she described on direct examination as colored by Sean Combs’ alleged control, threats and beatings.

In one exchange the defense pointed to, Ventura texted, “Freak off w/a girl” and Combs responded, “What makes you wanna do that”

Defense attorney Anna Estevao asked, “You were suggesting a freak off with a girl?”

Ventura responded flatly, “That’s what it says.”

“That’s what you were suggesting at the time?” Estevao followed up. “That’s what I was suggesting,” Ventura replied.

Estevao said the exchange followed an earlier conversation between Ventura and Combs about getting their relationship “to a good place.”

The defense also appeared to question Ventura’s recollection of when an alleged rape occurred, suggesting she switched the date from September 2018 to August 2018.

Around that time, Ventura received a message from Combs saying, “I know I look bad to you. I could tell I didn’t turn you on yesterday. I fell off. I’m about to get my s--- together.”

Ventura had previously testified on Wednesday that Combs allegedly raped her in her living in room in 2018. Combs and Ventura broke up the same year.

Related Topics

Sponsored Content by Taboola