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, 3:28 PM EDT

Ventura testifies on infidelity, anger from both parties in relationship with Combs

There was infidelity and jealousy on both sides in Cassie Ventura's tumultuous relationship of Sean Combs, Ventura testified under cross-examination.

The defense instructed Ventura to read aloud a past message she sent to Combs that read: “You are making me look like a side piece and that’s not what I thought I was.”

Casandra "Cassie" Ventura is cross-examined by lawyer Anna Estevao during Sean "Diddy" Combs' sex trafficking trial in New York City, May 15, 2025, in this courtroom sketch.
Jane Rosenberg/Reuters

Defense attorney Anna Estevao asked Ventura, “It was disappointing and hurtful to find out you weren’t the main girlfriend?”

“Yes,” Ventura replied. “It didn’t pertain to every situation but I was definitely jealous of certain situations he was in.”

“If he suspected you were in relationships with other men, he became insanely jealous?” Estevao asked, referring to Combs. “That’s when he lost his temper?

“A number of times,” Ventura answered.

Ventura had previously testified that Combs “lunged” at her during a "freak off" when he examined her phone messages and discovered that she had been seeing Scott Mescudi, aka rapper Kid Cudi.

“Did you feel justified in cheating on him with Mr. Mescudi because of Mr. Combs’ infidelities?” Estevao asked.

“I could have, I don’t know,” Ventura answered.

Ventura testified that she would have text-message arguments with Combs about cheating, during which he would bring up Kid Cudi.

“He would bring it up quite a bit,” Ventura told the court.

Ventura testified that in 2015, she was in South Africa shooting the film "Honey 3: Dare to Dance" when she learned Combs was back with a former girlfriend. “I was definitely angry,” Ventura testified.

At the same time, Ventura said she began a relationship with the actor Michael B. Jordan.

May 15, 2025, 2:31 PM EDT

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.

Lawyer Anna Estevao cross-examines Casandra "Cassie" Ventura during Sean "Diddy" Combs' sex trafficking trial in New York City, May 15, 2025, in this courtroom sketch.
Jane Rosenberg/Reuters

“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."

May 15, 2025, 2:42 PM EDT

Defense continues questioning Ventura about message exchanges with Combs

Before the jury returned from lunch, Judge Arun Subramanian made it clear that he expected the defense to finish its cross-examination of Cassie Ventura 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.

Subramanian said that Ventura is “not the kind of witness that is fighting” the defense's questions and suggested that the defense “streamline” its cross-examination.

The cross-examination so far has come in fits and starts, with defense attorney Anna Estevao seeming to have difficulty establishing a consistent rhythm. She has sometimes failed to properly introduce exhibits.

The defense strategy so far today has been to present to the court examples of messages exchanged between Ventura and Combs in an attempt to highlight what the defense contends is Ventura’s willingness, eagerness and agency to participate in "freak off" sex sessions, seeking to bolster Combs’ assertion that he did not commit sex trafficking.

Estevao continued that strategy after the break, showing more messages. In one, from March 18, 2017, Ventura told Combs, “I love our f.o.’s when we both want it," referring to the "freak offs."

“I would say loving f.o.’s were just words at that point,” Ventura testified in response.

“Those were words you said to Mr. Combs, correct?” Estevao asked. Ventura affirmed that they were.

In another message to Combs, sent ahead of a "freak off," Ventura said she was at a sex shop “trying to find something to impress you.”

Seeking to counter Ventura's previous testimony in which she denied being a willing participant in "freak offs" and their being video recorded, the defense showed another message from 2017.

“S---, I left the iPad. Should I go get?” Ventura’s message to Combs read.

“He would want it for a freak off?” Estevao asked Ventura.

“Yes,” Ventura replied.

“And you told him you would go get it?” Estevao asked.

“Yeah,” Ventura answered.

May 15, 2025, 1:14 PM EDT

Cassie Ventura testifies about Combs' fashion advice, alleged drug use

Cassie Ventura has previously testified that one way Sean Combs controlled her was to mandate aspects of her appearance, from her manicure color to her clothing, her hairdo and piercings. The defense today elicited testimony from her on cross-examination that sought to establish that Combs, who launched his successful Sean John men's fashion brand in 1998, is someone whose thoughts on fashion are in demand.

“Do you believe Mr. Combs has good taste?” defense attorney Anna Estevao asked.

“I think he does,” Ventura testified.

“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’ alleged drug use. In previous testimony, Ventura said that she witnessed a lot of drug use by Combs during their relationship and that there were times when both of them were heavily dependent on opiates. She testified that withdrawal from them made Combs "irritated."

The defense has attributed some of Combs’ violence, about which Ventura has previously testified, 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,” Ventura responded, earning a chuckle from the courtroom. She then testified that Combs was addicted to various substances over the years.

The court then took a break for lunch.

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