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Sean Combs sex trafficking trial updates: Ventura admits jealousy over Combs' other relationships

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

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Last updated: Thursday, May 15, 2025 11:27PM GMT
DIDDY ON TRIAL: Ventura cross-examination Day 1 recap
DIDDY ON TRIAL: Ventura cross-examination Day 1 recapABC News Legal Analyst Channa Lloyd breaks down day 1 of the cross-examination of Cassie Ventura.

NEW YORK -- The R&B singer Cassie will return to the witness stand on Friday after spending hours under cross-examination following two days of testimony recounting tumultuous details of life with her ex-boyfriend, Sean "Diddy" Combs.

Cassie read aloud her explicit messages with Combs on Thursday.

In some of the messages, she expresses enthusiasm for the sex encounters with other men orchestrated by Combs that she disparaged in previous testimony. Cassie testified on Wednesday that Combs raped her in 2018 and coerced her into participating in the so-called "freak-off" sex encounters with male escorts that made her feel ashamed.

Prosecutors allege Combs, 55, used his fame and fortune to orchestrate an empire of exploitation, coercing women into abusive sex parties.

If Combs is convicted on all charges, which include racketeering, kidnapping, arson, bribery and sex trafficking, he would face a mandatory 15 years in prison and could remain behind bars for life.

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

"Bad Rap: The Case Against Diddy," a new podcast from "20/20" and ABC Audio, traces how the whispers of abuse came to light and led to the downfall of Sean "Diddy" Combs, who was once among the most influential entertainers and entrepreneurs in hip hop. Listen on Apple Podcasts, Spotify, Amazon Music and more.

Kemberly Richardson reports from Lower Manhattan.

(ABC News and The Associated Press contributed to this report.)

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May 15, 2025, 5:21 PM GMT

And now, the questioning turns to the 'freak-offs'

The sexual events Combs staged dominated much of the testimony from Tuesday and Wednesday. Now Estevao is asking about the subject and displaying text messages to the jury in an apparent effort to show Cassie's enthusiasm for them. Estevao is reading Combs' parts of the email and text exchanges and having Cassie recite what she wrote to him at the time.

These communications between Cassie and Combs are graphic - describing for example what she wanted to do during the 'freak-offs' - and Estevao is making Cassie read them out loud, word by lurid word, while the lawyer reads Combs' parts.

The judge is allowing these emails, which don't discuss what happened, but rather what she was anticipating or wanting to have happen at the time.

After an extensive discussion on what evidence the defense could present, the judge disallowed messages reflecting attempts by Combs to learn whether Cassie was having sex with other men she was dating. So far, these other messages have been within the boundaries set by the judge.

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May 15, 2025, 4:08 PM GMT

Defense has Ventura read emails, messages exchanged with Combs

The defense has Cassie reading out loud from the warm emails and messages she exchanged with the hip-hop star early on. Portraying them to jurors as a loving, caring couple is a counterpoint to two days of testimony about forced sex and violence.

Combs was charismatic, with a larger-than-life personality, she testified. "I had fallen in love with him and cared about him very much," she acknowledged.

But another message Cassie read points to fractures in their relationship, which according to her earlier testimony devolved into violence and Combs' increasing obsession with seeing her have sex with strangers during drug-fueled sex parties he called "freak-offs."

In an April 2010 email, she expressed disappointment that Combs would rush her off the phone and wasn't spending time with her.

Cassie read the email in court: "That's not being in a relationship with someone that you love and are in love with ... I am really hurt by the way you deal with me, I don't need your money, I need some attention."

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May 15, 2025, 3:07 PM GMT

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.

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May 15, 2025, 2:05 PM GMT

The cross-examination seems gentle, for now

Defense attorney Anna Estevao has begun by questioning Cassie in a gentle tone of voice. It's notable because so many cross-examinations can begin with efforts to unsettle and agitate a witness. This approach was the opposite as Estevao began by asking about their relationship. Cassie responded yes to a series of questions.

- "You and Sean Combs were in love for 11 years. You loved him and believed that he loved you as well."

- "Yes."

- Your love of Combs explained explained "why it hurt so badly when he lied."

- "Yes."

- "When he cheated on you," Estevao continued.

- "Yes, Cassie said.