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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.)

ByAaron Katersky ABCNews logo
May 15, 2025, 6:51 PM GMT

Cassie Ventura recounts moments of jealousy as defense digs into relationship with Combs

Cassie Ventura admitted under cross-examination she "had some jealousy" of Kim Porter, mother of four of Sean Combs' children.

She also conceded that she became upset when she learned Combs had not broken off a relationship with a woman he had previously dated.

"Spending time with other women prompted arguments?" defense attorney Anna Estevao asked.

"Yeah," Ventura responded.

"And Mr. Combs had suspicions you were not faithful to him, correct?" Estevao followed up.

"Yeah," Ventura responded, adding that it could be "a little scary" when Combs suspected she had been unfaithful.

The defense has previously asserted that Ventura and Combs' relationship was plagued by infidelity, jealousy and violence on both sides.

The text exchanges the defense introduced Thursday included sexually explicit messages and talk of arranging "freak offs" commingled with more mundane subjects, like a discussion of going to see the Broadway show "The Book of Mormon." The defense attempted to assert that Combs and Ventura enjoyed moments of what Ventura previously testified were "romantic vibes," while also showing that she was a willing and eager participant in the "freak offs."

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May 15, 2025, 5:57 PM GMT

Defense tells judge Cassie may have to return next week; judge disagrees

Combs' lawyers said they don't expect to be done questioning Cassie until the end of the day on Friday. If that happens, it's possible she'll need to come back to court on Monday so prosecutors can ask her more questions during a phase of testimony known as re-direct.

Subramanian noted that the sides had previously agreed that she would be done by week's end, since she's pregnant and due to give birth soon to her third child.

The defense's revised timing "is the exact opposite of what I was told," the judge said.

"That is why there is a sword that I must fall on," Combs' lawyer Marc Agnifilo responded. He suggested that prosecutors muddled the timing by calling two witnesses before bringing Cassie to the stand.

Before the jury returned from lunch, Judge Subramanian made clear he expected the defense to finish its cross-examination by the middle of the day Friday.

"You have a day and a half. We should be done by the lunch break Friday," the judge said.

He noted that Ventura is "not the kind of witness that is fighting" the defense questions and suggested the defense "streamline" its cross-examination.

The cross-examination so far has come in fits and starts with defense attorney Anna Estevao unable to establish a consistent rhythm. She has sometimes failed to properly introduce exhibits and prosecutors have objected to several of her questions.

How it lands is up to a jury that skews male and skews older. The defense strategy so far is to show examples that appear to show Ventura's willingness, eagerness and agency as they seek to underpin Combs' assertion that he did not commit sex trafficking.

The Associated Press and ABC News contributed to this information.

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May 15, 2025, 5:45 PM GMT

Cassie on Comb's drug use: 'I would say he was an addict'

After Cassie Ventura testified that one way Sean Combs controlled her was to mandate her appearance, from her manicure color to her clothing, her hairdo and piercings, the defense elicited testimony from her on cross-examination that established Combs as someone whose thoughts on fashion were in demand.

"Do you believe Mr. Combs has good taste?" defense attorney Anna Estevao asked. "I think he does," Ventura responded.

"Is he known for his impact on fashion?" Estevao asked. "Yup," Ventura answered. "I would say he's had a big impact on fashion over many decades." She added, "Sometimes I got information without asking for it."

The defense also asked Ventura about Combs' drug use. She said she witnessed a lot of drug use by Combs during their relationship and testified there were points when both of them were heavily dependent on opiates.

She said withdrawal from them made Combs "irritated."

The defense has attributed some of Combs' violence to his drug use.

"You would say he was an addict?" Estevao asked. "I would say he was an addict," Ventura replied.

"What was he addicted to?"

"Success," she responded, earning a chuckle from the courtroom. She then said Combs was addicted to various substances over the years.

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May 15, 2025, 4:41 PM GMT

Was it all about a swingers lifestyle for Combs?

Defense lawyers made it clear before the trial that they intended to label a lot of Combs' sexual behavior as reflective of a swingers lifestyle.

Now Estevao is asked Cassie directly if she thinks "freak-offs" were related to this lifestyle.

"In a sexual way," Cassie responded, before adding: "They're very different."

A day earlier, Cassie told prosecutors they went to swingers clubs together several times in Los Angeles and Las Vegas.

While prosecutors focused on Combs' desire to see Cassie having sex with other men in marathons of sexual activity, she acknowledged under defense questioning that she sometimes watched Combs have sex with other women.

Cassie testified that this happened maybe four times throughout the course of their decade-long relationship, and that Combs told her it was part of a "swingers lifestyle."