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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 15, 2025, 3:45 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 15, 2025 3:45 PM

Defense suggests Ventura wanted more from Combs relationship than just participating in his 'fantasies'

After testifying for two days that Sean Combs forced her into sexual encounters with male prostitutes under threat of violence and reputational harm, Cassie Ventura was confronted on cross-examination by messages that appeared to show her reluctance was only because she wanted more from the relationship.

“When we used to freak off when 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 wrote in a message to Combs from December 2009. "I get nervous that I’m just becoming the girlfriend that you get your fantasies off with and that’s it. I don’t get the other part."

PHOTO: Sean "Diddy" Combs takes notes during the morning arguments in his sex trafficking trial in New York City, May 15, 2025, in this courtroom sketch.
Jane Rosenberg/Reuters
Sean "Diddy" Combs takes notes during the morning arguments in his sex trafficking trial in New York City, May 15, 2025, in this courtroom sketch.
Jane Rosenberg/Reuters

“At the time you were afraid that you were being treated as someone who he could just get his fantasies off with?” defense attorney Anna Estevao asked.

“That was a concern,” Ventura answered.

Estevao asked Ventura whether "freak offs" were a “defining feature” of their relationship.

“It became a very integral part of our relationship early on,” Ventura responded.

“And you wanted your relationship to develop more?” Estevao asked.

“Right,” Ventura said.

The defense showed the court additional explicit messages, meant to support their contention that Ventura was an eager sexual partner who shared Combs’ desires.

In one August 2009 message exchange, Ventura expressed, with explicit detail, excitement about a then-forthcoming sexual event.

“I can’t wait. That’s what I want to see,” Combs replied.

“I can’t wait either,” Ventura wrote back.


May 15, 2025 3:07 PM

Ventura questioned about loving, explicit messages exchanged with Combs

Ventura testified that she loved Combs and believed he loved her, and that the two exchanged “loving” messages.

The jury was shown one such message from early in their relationship. “It makes me so happy that you would fly to ATL just to see me. I’m a very lucky man,” an email from Combs read.

“I’m a very lucky woman. I miss you so much. I’d fly wherever you needed me, whenever,” Ventura sent in reply.

“What about him made you fall in love with him?” defense attorney Anna Estevao asked Ventura.

“I haven’t thought about it in a while," Ventura responded. "The beginning of the relationship, I spoke about it already, it was really fast, fast-paced, scary. But the more time I spent with him and got to know him his real personality, or at least what I thought was his real personality, came out,”

Ventura further testified that Combs in the early stages of their relationship was “very sweet, attentive.”

The jury was shown an August 2009 message from Combs to Ventura, telling her to look at his latest tweet. Ventura responded “OMG!!! Pop pop … Can I respond or write something about my man," using a nickname for Combs that she testified on Tuesday Combs had requested.

Ventura testified that at the time she was looking forward to going public about their relationship.

In another message, from April 4, 2010, two-and-a-half years into their relationship, Ventura sent a message to Combs that read “I love you so much it consumes my life.”

The defense has argued that Ventura was not sex trafficked, as the prosecution claims, but rather was a willing partner in what the defense has described as Combs’ “swingers lifestyle.” Ventura pushed back against a defense attorney’s suggestion that she willingly partook in so-called "freak off" sex sessions.

“To make him happy you told him that you wanted to do 'freak offs',” defense attorney Anna Estevao said.

“No,” Ventura replied. “There’s a lot more to that.”

Estevao then confronted Ventura with a message from August 5, 2009, in which Ventura told Combs, “I’m always ready to 'freak off.'”

Two days later, the defense said Ventura sent Combs an explicit message expressing excitement about participating in a sexual event.

Combs responded, “I can’t wait to watch you. I want you to get real hot.”

Ventura replied, “Me too. I just want it to be uncontrollable.”

After the defense introduced an additional, explicit, message, Ventura asked the judge for a break.


May 15, 2025 2:29 PM

Defense begins cross-examination of Cassie Ventura

Defense lawyer Anna Estevao said she expected the cross-examination of Cassie Ventura to last all of Thursday and into Friday. Federal prosecutors told the judge that Ventura must finish her testimony by the end of the day Friday because she “is very, very pregnant” and could go into labor soon.

“We are afraid she could have the baby over the weekend,” Assistant United States Attorney Maurene Comey said.

Ventura took the witness stand in a long black tuxedo-like jacket covering a light-colored blouse.

Combs, clad in light-colored pants, shirt and sweater, watched her enter. His family is seated in the gallery

“You and Sean Combs were in love for 11 years, right?” Estevao's questioning began.

“Yeah,” Ventura responded.



May 15, 2025 1:42 PM

Cassie Ventura takes the stand ahead of cross-examination

Cassie Ventura has taken the witness stand for the third consecutive day, with defense cross-examination scheduled to begin this morning following two days of her testimony against Sean 'Diddy' Combs.


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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