Cassie faces cross-examination in Sean 'Diddy' Combs sex trafficking trial

NEW YORK (TNND) — After being on the stand for about nine hours between Tuesday and Wednesday, Cassie Ventura is facing cross-examination from Sean "Diddy" Combs' defense team on Thursday.

Lawyers for Combs are seeking to portray Ventura as a willing participant in his sexual lifestyle and say that, while he could be violent, nothing he did amounted to a criminal enterprise.

Ventura, 38, considered to be the key witness in the sex-trafficking trial, spent the past two days describing in detail to prosecutors the disturbing acts Combs allegedly had her commit during "freak offs" and provided background on the hotel surveillance video made public by CNN showing Combs beating her at a Los Angeles hotel in 2016.

The defense is planning on finishing Ventura's cross-examination by the end of the day Friday so that her testimony concludes before her baby arrives. Ventura is set to give birth to her third child next month.

Combs, 55, has pleaded not guilty to a five-count indictment and faces a minimum sentence of 15 years in prison and a maximum sentence of life in prison if convicted on all charges. He is facing charges of sex trafficking by force, fraud, or coercion, transportation for purposes of prostitution, and racketeering conspiracy.

Prosecutors say he exploited his status as a powerful music executive to violently force Ventura and other women to take part in these encounters with sex workers, which he called “freak-offs,” and of using his network of employees to facilitate illegal activities, which is a key part of the racketeering charge.

Before cross-examination started Thursday morning, prosecutors and defense attorneys argued about the type of text messages the defense could show to the jury. The defense wanted to use "colorful" text messages between Ventura and Combs from when Combs thought Ventura was seeing other people, according to CNN.

PHOTOS: Outside the sex-trafficking trial of Sean 'Diddy' Combs

The National News Desk's Geoff Harris was outside the courtroom in Manhattan on Monday and Tuesday to cover the beginning of what is expected to be a two-month-long trial.

The Associated Press reported from inside the courtroom Thursday that defense attorney Anna Estevao began questioning Ventura in a gentle tone of voice compared to cross-examinations beginning with efforts to unsettle or agitate a witness.

“You and Sean Combs were in love for 11 years. You loved him and believed that he loved you as well,” Estevao said. The attorney said Ventura's love explained, “Why it hurt so badly when he lied. ... When he cheated on you.” Ventura responded “Yes” to both.

Estevao went on to show the jury messages from the early part of Combs and Ventura's relationship that exhibited kindness and love, with Estevao reading aloud what Combs said while Ventura recited what she wrote to him.

In April 2010, Cassie told Combs: “Going to sleep now so it can be tomorrow faster and you can be home. Love you!!!” Combs replied: “Love my baby.”

Ventura read numerous explicit messages, including some in which she described in graphic detail what she wanted to do during the freak-offs. At one point, she asked for a short break from the readings, which the judge granted.

In August 2009, Combs asked her when she wanted to have the next episode, and she replied, “I’m always ready to freak off.” Two days later, Ventura sent an explicit message, and he replied in eager anticipation. She responded: “Me Too, I just want it to be uncontrollable.” Combs' lawyers have insisted that all the sex at the freak-offs was consensual.

Later that year, however, she had also sent Combs messages that she was frustrated with the state of their relationship and needed something more from him than sex.

As the messages were read, Combs appeared relaxed at the defense table, sitting back with his hands folded and his legs crossed. Combs was also seen passing sticky notes to his attorney during Ventura's testimony, according to CNN.

While prosecutors have focused on Combs’ desire to see Ventura having sex with other men, she testified that she sometimes watched Combs have sex with other women. She said Combs described it as part of a “swingers lifestyle.”

Estevao asked Venturaa directly whether she thought freak-offs were related to the swingers lifestyle.

“In a sexual way,” Ventura responded, before adding: “They’re very different.”

Ventura has testified that these encounters were fueled by drugs and would last hours and even days, with her sometimes taking IV fluids to recover and eventually developing an opioid addiction because it made her “feel numb” afterwards.

More messages about the "freak offs" were shown to the jury, with one conversation having Ventura asking Combs to stop playing the victim, according to CNN.

"That's all you wanted and that's why I was upset," Ventura wrote, "I love our ["freak offs"] when we both want it."

Defense read messages between Combs and Ventura, with Combs telling Ventura that he had a "surprise package coming from out of state," CNN reported.

Ventura confirmed that Combs would occasionally be the one to pick up supplies or contact escorts when preparing for a "freak off."

Estevao read out some of the text messages Combs sent to Ventura, with him saying "didn't hear from you so I just put some plans in motion let me know to stop," and "just let me know if I'm headed in wrong direction so I can cancel."

Defense also tried to confirm with Ventura that the baby oil that was used during "freak offs" was not laced with drugs, but the judge sustained an objection to the question.

On Wednesday, Ventura confirmed for the first time that she settled a civil suit with Combs for $20 million in 2023, CNN, who was permitted to be in the courtroom, reported. Ventura said she wrote a book in 2023 about the pain she was in from what she experienced with him and that she sent the book through a lawyer to Combs, offering him the rights to the book for $30 million.

I wanted to be compensated for the time, the pain, the many many years of having to fix my life.

As further proof of the alleged abuse, jurors were shown photos from prosecutors of the "freak off" videos, which Ventura claimed Combs would regularly threaten to publicize. She said she felt trapped and didn't want to make him angry.

When asked by a prosecutor if she would ever try to fight back against Combs, Ventura said she tried to earlier in the relationship, but she learned that "it could escalate the fight more, make it worse for myself."

Combs’s attorneys argued Monday that he could be violent but never participated in sex trafficking and racketeering, telling jurors that the sexual acts were consensual.

Estevao suggested that Combs was going through withdrawals before he assaulted Ventura at a hotel in 2016. A series of text messages were reviewed from the week before the altercation with Ventura and Combs discussing symptoms that the defense suggests are withdrawal side effects. Some of these messages were shown during Ventura's direct examination.

Ventura said that she doesn't remember if Combs was going through a withdrawal at that time.

Defense also tried to suggest that Ventura was encouraging the planning of a "freak off" with her messaging Combs, "We can have fun, I don't want you thinking I don't want to." Ventura testified that the messages were his way of asking her to participate in a "freak off" since he kept asking about her plans for the night.

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Ventura testified that Combs would threaten to release the recordings of the "freak offs," saying that she was always worried that he would get mad enough to release them to the public.

“I feared for my career. I feared for my family. It’s just embarrassing. It’s horrible and disgusting. No one should do that to anyone,” she said.

She said that her friends and family knew that Combs physically abused her.

According to Ventura, Combs overdosed on painkillers in 2012 after they had a "freak off" and went to a sex club. She said that he went to a party at the Playboy Mansion without her that night, and she later took him to the hospital.

“From what he told me, he took a very strong opiate that night, but we didn’t know what was happening, so we took him to the hospital,” Ventura testified.

Ventura told prosecutors she developed an opioid addiction after using them following the “freak offs” as a coping mechanism, and at one point wanted to commit suicide.

"I couldn’t take the pain that I was in anymore, and so I just tried to walk out the front door into traffic, and my husband would not let me," she testified.

Ventura said that in 2017, she got sick from her drug use and started to seek help.

“I lost all sense of smell and taste when I woke up, and I had numbing in my arm,” Ventura said. She said that both she and Combs did a lot of drugs during their relationship.

In 2018, after going to dinner for a "closure conversation" to end the relationship, Ventura told the jury Combs raped her in her living room, according to CNN.

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While testifying about other women who were involved with Combs, Ventura said that she "had some jealousy" of Kim Porter, who shared three children with Combs, according to CNN.

Porter died in 2018.

Ventura said that she would be upset when he spent holidays with his children and Porter, even though he and Porter were not together. In 2013, Ventura testified that she felt frustrated about not being able to form a relationship with Combs' children.

“I’ve been at the edge of tears this whole week. I don’t think that you sympathize with my feelings. I understand you feeling like you need to protect your children but after a while It’s like for what? They’ve never known you and Kim [Porter] to be together. Unless there’s something that I just don’t know about. They were babies when we started dating.”

She also said that in April 2014, she found out that Combs was spending time with a woman named "Gina," which made her upset. Ventura said that Combs denied being in a relationship with "Gina," but they argued over it, as well as other women he was involved with.

On social media, women would claim to be in a relationship with Combs, Ventura testified. She said that "Gina" was one of the main problems in their relationship.

When Ventura was in a relationship with rapper Kid Cudi, Scott Mescudi, she got a burner phone so Combs would not find out about their relationship.

Combs was the one to introduce the two around 2011 to work on music with each other. Ventura started dating Kid Cudi when Combs and her were on a break, according to CNN.

While she was dating Kid Cudi, she still participated in "freak offs" because "it was a job." Ventura said that Combs would bring up her relationship with Kid Cudi a lot, especially when she would accuse Combs of cheating on her.

During questioning, Estevao brought up how Combs had suspicions that Ventura was seeing Michael B. Jordan. Ventura said she didn't know how Combs responded to these suspicions because she wasn't with him at the time to see his reaction.

By 2015, Ventura broke up with Combs while she was in South Africa shooting a movie. She said she sent him a video of him with another woman in a group chat with some of his staff and then blocked his number for the majority of her filming.

Ventura said she met Combs in 2005 when she was 19 and he was 37. He signed her to his Bad Boy Records label and, within a few years, they started dating platonically before the alleged abuse began.

Combs was arrested in September 2024, about roughly six months after federal authorities raided his homes in Los Angeles and Miami. He has been jailed in Brooklyn since his arrest.

If you or someone you know is struggling with abuse, contact the National Domestic Violence Hotline for help.

Editor's Note: The Associated Press contributed to this story.