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 15, 2025, 11:00 AM EDT

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, 10:08 AM EDT

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, 9:41 AM EDT

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 14, 2025, 5:29 PM EDT

Court adjourns after dramatic Cassie Ventura testimony

Judge Arun Subramanian opted to adjourn court for the day and begin the defense's cross-examination of Cassie Ventura on Thursday.

The defense said it expected cross-examination to take all of Thursday and that it will likely continue into Friday, followed by redirect examination by the prosecution.

Ventura is off of the witness stand and has been excused for the day.

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