Sean 'Diddy' Combs trial updates: Cassie Ventura breaks down as testimony concludes

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."

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.

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.

Cassie Ventura testified on cross-examination that she fell in love with Sean Combs soon after they met.

“We’ve only really had one week of each other just together and I can say that it’s been the best and worst,” Ventura wrote in a 2007 message to Combs, which was shown to the court. “I’m sad, mad, frustrated and hurt that you just don’t feel like I’m the right one.”

Ventura testified that the message made her “giggle” because it is nearly 20 years old. “I’m reading it like a journal entry,” she said.

Defense attorney Anna Estevao asked Ventura whether the message reflected her “dreaming up a beautiful future together” with Combs.

Ventura replied, “Mm hm.”

The defense also questioned Ventura regarding the ramifications of her 2023 civil lawsuit against Combs.

“When your lawsuit was publicized in 2023 you understood his career was ruined?” Estevao asked.

“I could understand that,” Ventura replied.

The defense highlighted messages exchanged between Ventura and Combs in July 2012, in which Combs appeared to be interested in Ventura’s desires, which, she previously testified, did not matter to him.

“One of my favorite times was when we f.o.’d and then made love after,” Combs messaged her, referring to the so-called "freak off" sex sessions.

“I love when we make love after," Ventura responded in part, followed by an explicit sexual reference.

The defense appeared to be highlighting occasions in which they argue Ventura had more agency in her relationship with Combs than she previously testified.

“Often after a session of a 'freak off' you would make love?” Estevao asked.

“Afterwards, yeah,” Ventura replied.

“And you’re telling him that you love it?” Estevao asked.

“With him, yeah,” Ventura replied.

“He also told you that he loved it when you made love after?” the defense attorney asked.

“That’s what it says," testified Ventura.