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

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.

After testifying for two days that Sean Combs forced her into sexual encounters with male prostitutes under threat of violence and reputational harm, Cassie Ventura was confronted on cross-examination by messages that appeared to show her reluctance was only because she wanted more from the relationship.

“When we used to freak off when were so in love. There were no questions asked, it felt right, like it literally made sense for the next step in our sex life together," Ventura wrote in a message to Combs from December 2009. "I get nervous that I’m just becoming the girlfriend that you get your fantasies off with and that’s it. I don’t get the other part."

“At the time you were afraid that you were being treated as someone who he could just get his fantasies off with?” defense attorney Anna Estevao asked.

“That was a concern,” Ventura answered.

Estevao asked Ventura whether "freak offs" were a “defining feature” of their relationship.

“It became a very integral part of our relationship early on,” Ventura responded.

“And you wanted your relationship to develop more?” Estevao asked.

“Right,” Ventura said.

The defense showed the court additional explicit messages, meant to support their contention that Ventura was an eager sexual partner who shared Combs’ desires.

In one August 2009 message exchange, Ventura expressed, with explicit detail, excitement about a then-forthcoming sexual event.

“I can’t wait. That’s what I want to see,” Combs replied.

“I can’t wait either,” Ventura wrote back.

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.