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, 9:47 AM EDT

Cassie Ventura takes the witness stand for 4th day

Cassie Ventura has taken the witness stand for the fourth consecutive day to continue her cross-examination in the trial against her ex-boyfriend Sean "Diddy" Combs.

May 16, 2025, 9:11 AM EDT

Federal prosecutors claim defense is attempting to prolong Cassie Ventura's cross-examination in letter to judge

Defense lawyers for Sean Combs are trying to prolong their cross-examination of Cassie Ventura into next week, hoping to "risk a mistrial if the witness goes into labor," federal prosecutors said in an overnight letter to the judge.

The letter pointed to the "inefficiency" of the defense cross examination as proof the defense "hopes to accomplish precisely that outcome."

Prosecutor's argued that Ventura was often made to read long excerpts of text messages with no real question, an approach prosecutors called a "filibuster" and asked the judge to order the defense to finish by 4:30 Friday, allowing a half hour for re-direct.

Prosecutors said defense counsel has known for weeks about Ventura’s pregnancy and they earlier told the judge Ventura could have her baby as soon as this weekend.

The defense argues that they should have the right to thoroughly cross-examine the witness.

May 15, 2025, 5:32 PM EDT

Defense questioning Ventura's account of March 2016 hotel attack; court adjourns

The jury saw Cassie Ventura’s text messages from the days leading to the premiere of "The Perfect Match," about which she previously testified, and her "freak off" with Sean Combs at the InterContinental Hotel in March 2016.

“Thank you,” Ventura said after defense attorney Anna Estevao said she would spare Ventura from reading the explicit texts aloud.

At the time, Ventura said, Combs was not feeling well. The defense suggested he could have been suffering the effects of drug withdrawal in the days before the assault that was captured by hotel surveillance cameras.

The defense also suggested it was Ventura who pushed the idea of a "freak off" before the movie premiere, pointing to one message in which Ventura told Combs, “Baby I want to f.o. so bad but I don’t want to f--- myself up. What am I to do?”

“You proposed a 'freak off,'” Estevao said. “You kept asking him.”

The defense suggested Combs could have become violent during the "freak off" at the Century City InterContinental because he and Ventura took bad drugs.

“The drugs that you and Mr. Combs took that day were a bad batch of MDMA, right?” Estevao said.

“I have no idea,” Ventura testified.

Court has adjourned for the day. Ventura will return to the stand Friday.

May 15, 2025, 4:24 PM EDT

Defense questions Cassie Ventura's testimony on violence, drug habits

The defense questioned whether Cassie Ventura had really witnessed Sean Combs dangle one of her friends over a balcony, as she previously testified that she had.

“You learned about this after the fact,” defense attorney Anna Estevao said.

“I saw what I saw, so I don’t know,” Ventura answered.

The defense also questioned Ventura's prior testimony recounting a time when she alleged Combs and others went to confront record executive Suge Knight at a diner, and her account of Combs allegedly attacking her friend Kerry Morgan.

Estevao elicited testimony from Ventura about Combs’ alleged drug use and its effect on his moods. Ventura testified that Combs could be “pretty explosive.”

The defense also attempted to establish instances when Combs in turn worried about Ventura’s drug use.

“He wanted you to stop doing drugs,” Estevao said.

“He wanted me to stop doing drugs with other people,” Ventura responded.

The cross-examination at times became disjointed and meandering such that at one point, Estevao declared, “I know I’m all over the place.”

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