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

PHOTO: 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.
22:39
Jane Rosenberg/Reuters
Diddy Trial Day 5: Cassie Ventura breaks down on the witness stand
By Aaron Katersky, Mason Leib
Last Updated: May 16, 2025, 6:06 PM

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.

Key Headlines

  • Dawn Richard testifies about seeing Cassie 'attacked' by 'screaming, belligerent' Combs
  • Special agent's testimony concludes as prosecution calls Danity Kane's Dawn Richard to the stand
  • Special agent testifies to drugs, baby oil in Combs' hotel room at time of arrest
  • Cassie Ventura, Alex Fine share statement through attorney after 4-day testimony
  • Cassie Ventura concludes her testimony after 4 days
Here's how the news is developing.

Pinned
May 19, 2025 12:53 PM

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."


Pinned
May 12, 2025 9:40 PM

Male escort describes several alleged sexual encounters with Cassie Ventura at Combs' direction, claims Combs attacked Cassie

Daniel Phillip, a male escort, described several alleged sexual encounters he had with Cassie Ventura which he claims came at the direction of Sean Combs.

Phillip testified about one alleged encounter at the Gramercy Park Hotel, where he said he met Ventura and Combs.

It was the first of several sexual encounters Phillips testified that he'd had with Ventura and Combs at New York locations such as the Essex House, the InterContinental, Combs’ personal residence on West 56th St., and Ventura’s personal residence on West End Avenue.

During these alleged encounters, Phillip said Combs provided direction and instructions and said he was paid between $700 and $6,000 for each encounter.

Phillip testified about a time when he said he was given the drug “molly” during one of these alleged encounters. He claims there was another time when he saw Combs become physical with Cassie.

PHOTO: Escort, Daniel Philip, testifies on witness stand on the first day of Sean Diddy Combs' trial in Manhattan federal court, May 12, 2025, in New York.
Elizabeth Williams/AP
Escort, Daniel Philip, testifies on witness stand on the first day of Sean Diddy Combs' trial in Manhattan federal court, May 12, 2025, in New York.
Elizabeth Williams/AP

Phillip said Ventura was on her computer after a sexual encounter when Combs called out from the bedroom, “Babe come here.”

According to Phillip, Ventura responded, “Hold on one second” and that’s when he said Combs came out of the bedroom and “saw a bottle fly past her and hit the wall.”

“Mr. Combs walked over to Cassie, grabbed her by the hair and started dragging her to the bedroom,” Phillip said. “He wasn’t saying anything while he was dragging her. She was yelling. She was screaming. Mr. Combs pulled her into the bedroom and what I could hear sounded like him slapping her.”

Phillip said he overheard Combs allegedly saying “B---, when I tell you to come here you come now not later.”

Phillip said the alleged violence shocked him. “It came out of nowhere. I was terrified. I didn’t know what to do,“ he said.

Prosecutor Maureen Comey asked why he did not intervene.

“I’m just telling you what was in my mind. What I was feeling at the time. My thoughts were that this was someone with unlimited power and chances are that even if I did go to the police that I might still end up losing my life,” Phillip said.

When Ventura and Combs came out of the room, Phillip recalled Combs asking “Are y’all ready to continue now?”

Combs has been listening to this testimony slightly backed away from the defense table with his arms at his side and his legs crossed.


May 16, 2025 6:06 PM

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 5:42 PM

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 4:43 PM

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.

PHOTO: 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
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.



May 16, 2025 3:53 PM

Defense questions Ventura on PTSD and opiate addiction treatment

Cassie Ventura testified she has been taking Suboxone, a treatment for opiate addiction since 2022.

In 2023, she attended a 45-day in-patient treatment program in Arizona that included neuro-feedback therapy and EMDR, Eye Movement Desensitization and Reprocessing, a psychotherapy technique meant to help process distressing memories, according to her testimony.

“You understood that you were being treated for PTSD?” defense attorney Anna Estevao asked. “Yes,” Ventura testified. She denied being treated for sex or love addiction, which the facility also offers.

The testimony has been interrupted by calls for conferrals between the parties.

The judge called a recess to remind the defense of his rules and to impose new ones.


May 12, 2025 9:40 PM

Male escort describes several alleged sexual encounters with Cassie Ventura at Combs' direction, claims Combs attacked Cassie

Daniel Phillip, a male escort, described several alleged sexual encounters he had with Cassie Ventura which he claims came at the direction of Sean Combs.

Phillip testified about one alleged encounter at the Gramercy Park Hotel, where he said he met Ventura and Combs.

It was the first of several sexual encounters Phillips testified that he'd had with Ventura and Combs at New York locations such as the Essex House, the InterContinental, Combs’ personal residence on West 56th St., and Ventura’s personal residence on West End Avenue.

During these alleged encounters, Phillip said Combs provided direction and instructions and said he was paid between $700 and $6,000 for each encounter.

Phillip testified about a time when he said he was given the drug “molly” during one of these alleged encounters. He claims there was another time when he saw Combs become physical with Cassie.

PHOTO: Escort, Daniel Philip, testifies on witness stand on the first day of Sean Diddy Combs' trial in Manhattan federal court, May 12, 2025, in New York.
Elizabeth Williams/AP
Escort, Daniel Philip, testifies on witness stand on the first day of Sean Diddy Combs' trial in Manhattan federal court, May 12, 2025, in New York.
Elizabeth Williams/AP

Phillip said Ventura was on her computer after a sexual encounter when Combs called out from the bedroom, “Babe come here.”

According to Phillip, Ventura responded, “Hold on one second” and that’s when he said Combs came out of the bedroom and “saw a bottle fly past her and hit the wall.”

“Mr. Combs walked over to Cassie, grabbed her by the hair and started dragging her to the bedroom,” Phillip said. “He wasn’t saying anything while he was dragging her. She was yelling. She was screaming. Mr. Combs pulled her into the bedroom and what I could hear sounded like him slapping her.”

Phillip said he overheard Combs allegedly saying “B---, when I tell you to come here you come now not later.”

Phillip said the alleged violence shocked him. “It came out of nowhere. I was terrified. I didn’t know what to do,“ he said.

Prosecutor Maureen Comey asked why he did not intervene.

“I’m just telling you what was in my mind. What I was feeling at the time. My thoughts were that this was someone with unlimited power and chances are that even if I did go to the police that I might still end up losing my life,” Phillip said.

When Ventura and Combs came out of the room, Phillip recalled Combs asking “Are y’all ready to continue now?”

Combs has been listening to this testimony slightly backed away from the defense table with his arms at his side and his legs crossed.


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