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Sean 'Diddy' Combs trial day 9: Ventura spars with defense lawyers during final day of testimony

Cassie Ventura testifies on multiple instances of Combs' alleged intense jealousy - Ventura testified about a time in 2016 when she and Sean Combs were in a car and he allegedly swiped her phone from her hand, jumped from the vehicle and ran down Wilshire Boulevard in Los Angeles.

Cassie Ventura concluded four days of often painful and intimate testimony on Friday, as she sparred with attorneys for her former boyfriend, Sean "Diddy" Combs, over the consistency of her testimony and the harm she allegedly endured at the hands of the rap mogul.

Ventura's testimony, coming right at the start of the much-anticipated Combs criminal trial, appeared to lay a foundation for the prosecution's racketeering and sex-trafficking case against Combs. They allege Combs subjected Ventura to regular violence and blackmail threats to keep her in line so she would fulfill his sexual desires by arranging days-long sex parties called "freak offs" and "wild king nights."

Combs has pleaded not guilty to charges of sex trafficking, transportation to engage in prostitution and racketeering conspiracy, and his lawyers, through two days of cross-examination, attempted to reframe Ventura as a willing sex partner who enjoyed a swinger's lifestyle and contributed to an admittedly toxic relationship. His lawyers have acknowledged that Combs was violent with Ventura but argued his actions do not amount to sex trafficking or racketeering, as federal prosecutors have alleged. They also highlighted episodes when Ventura was violent toward Combs in order to prove their point that the ugliness that marked their relationship went both ways.

Lawyer Anna Estevao cross examines Casandra "Cassie" Ventura as Judge Arun Subramanian presides during Sean "Diddy" Combs' sex trafficking trial in New York City, May 16, 2025 in this courtroom sketch. Jane Rosenberg/Reuters
 

Ventura largely maintained her composure across two days of defense questioning, even as attorneys confronted her with text messages and emails replete with graphic sexual details, and some jurors appeared to lose focus during the at-times meandering and disjointed cross-examination. When his attorney Anna Estevao concluded the cross-examination, Combs embraced Estevao in court and appeared to thank her for the intense questioning.

When questioned by prosecutors one final time on Friday, Ventura broke down in response to questioning about how she suffered following the allegedly regular beatings from Combs, telling jurors that she felt "worthless, just like dirt, that I didn't matter to him, like I was nothing." Ventura told the jury she would return the $20 million civil settlement she received from Combs in 2023 if it meant she never had to participate in a freak off.

Sean 'Diddy' Combs listens as lawyer Anna Estevao cross examines Casandra 'Cassie' Ventura during Combs' sex trafficking trial in New York City, May 16, 2025 in this courtroom sketch. Jane Rosenberg/Reuters
Sean "Diddy" Combs listens as lawyer Anna Estevao cross examines Casandra "Cassie" Ventura during Combs' sex trafficking trial in New York City, May 16, 2025 in this courtroom sketch. Jane Rosenberg/Reuters
 
 

"I'd give that money back if I never had to do freak offs. I would have agency and autonomy," she said through tears. "I wouldn't have had to work so hard to get it back."

Defense lawyers attempt to recast moments of violence at the center of Ventura's testimony 

Defense attorneys focused on two central moments described by Ventura during her direct examination: a 2016 assault at a Los Angeles hotel and an alleged rape near the end of their relationship. During cross-examination, Combs' lawyers attempted to use those episodes to cast doubt on Ventura's credibility.

Asked about the 2016 hotel assault, Ventura said she believed Combs was intoxicated during the encounter. On Thursday, during Ventura's third day of testimony, defense attorneys tried to suggest the drugs he was taking at the time contributed to his violence.

"When you get f------ up the wrong way you always want to show me you have the power and knock me around. I'm not a rag doll. I'm someone's child," Ventura wrote in a text message after the incident that was entered into evidence Friday.

Defense attorney Anna Estevao also probed Ventura about her recollection of how her relationship with Combs ended. The once-up-and-coming singer testified earlier in the week that Combs raped her after a dinner she said they planned as their relationship was coming to a close. 

Casandra 'Cassie' Ventura is cross examined by Lawyer Anna Estevao during Sean 'Diddy' Combs' sex trafficking trial in New York City, May 16, 2025 in this courtroom sketch. Jane Rosenberg/Reuters
Casandra "Cassie" Ventura is cross examined by Lawyer Anna Estevao during Sean "Diddy" Combs' sex trafficking trial in New York City, May 16, 2025 in this courtroom sketch. Jane Rosenberg/Reuters
 

"You don't say anything to the effect of, 'the last time we saw each other you raped me,'" Estevao said of Ventura's messages with Combs at the time.

Earlier, the defense showed Ventura transcripts of her interviews with law enforcement agents, pointing out that she told them the night of the alleged rape Combs was acting "nice but strangely." The defense also pointed out how Ventura wondered whether the alleged attack occurred because of Combs's bipolar disorder, the first time such a diagnosis was mentioned at trial. Combs has previously said he is not bipolar but has mood swings.

Defense lawyers focus on Ventura's alleged infidelity

During cross-examination, the defense introduced scores of text messages that contained a mix of affection, sexually-charged banter, domestic negotiation, bickering and jealousy. Jealousy first emerged as a central tenet during the defense's opening statements, when Combs' lawyers told the jury the case against their client is about "love, jealousy, infidelity and money."

Ventura recounted how Combs would grow jealous if he suspected she was seeing another man, and on multiple occasions, took her phone from her to learn about the suspected infidelity.

"Mr. Combs was insanely jealous?" defense attorney Anna Estevao asked. "He was upset with you when he suspected you of cheating?"

Ventura responded, "When I was with anyone else. I don't know if I would call it cheating."

Estevao said, "You understood he thought it cheating?"

Ventura responded, "That's a technicality. We weren't married."

Defense attorneys attempt to show different side of Ventura 

Jurors heard a dramatic audio recording of a March 2014 conversation in Atlantic City between Ventura and a man called Sugit, who had told her he had seen her in a sexually explicit video taken during a "freak off." Multiple jurors appeared attentive and took notes during the testimony, as they heard a markedly more aggressive version of Ventura than had appeared on the stand, who herself seemed amused by the reaction captured on tape.

"Tell me what exactly you saw," Ventura is heard telling Sugit. "You told me somebody else was in there f------- me."

A moment later, her voice is heard rising. "You have it? Why didn't you show me?" Ventura asked.

"Because I'm not disrespectful," Sugit is heard answering meekly.

"You've had it the whole time?" Ventura said. "It's my f****** life and I'll kill you. I'll kill you if you don't show me. Pull it up. If you have it, pull that s--- up or I'm going to kill you!"

Ventura acknowledged the aggressiveness in her voice, having testified on direct examination about a constant fear that Combs might release the sex tapes from freak-offs that would destroy her career and her reputation. Ventura testified that Combs had shown her the videos and used them as blackmail, threatening to release them if she disobeyed him.

"I was just sick about it and was feeling pressure from Sean," Ventura told jurors, adding that Combs directed her to speak with Sugit.

At the conclusion of her testimony, Ventura, through a statement read by her attorney Douglas Wigdor outside court, thanked her supporters for their kindness and vowed to never forget what she said Combs did to her.

"I hope that my testimony has given strength and a voice to other survivors and can help others who have suffered to speak up and also heal from abuse and fear. For me, the more I heal, the more I can remember, and the more I can remember, the more I will never forget," she said in a statement.

Prosecutors call federal agent, Dawn Richard of Danity Kane to witness stand 

Federal prosecutors called two additional witnesses on Friday after the conclusion of Ventura's testimony.

Special Agent Yasin Binda of Homeland Security Investigations told jurors about a search of Combs' hotel room at the time of his arrest in 2024, when his lawyers said he traveled to New York to surrender to authorities. Binda testified that agents seized $9,000 in cash, substances that later tested positive for ketamine and MDMA, multiple bottles of baby oil, and a device used for "mood lighting," which Ventura alleged were the kind of items Combs would use during freak offs. Jurors were able to touch and examine some of the materials seized from Combs' room.

Sean 'Diddy' Combs and his defense team pass notes during the cross examination of Casandra 'Cassie' Ventura during Combs' sex trafficking trial in New York City, May 16, 2025 in this courtroom sketch. Jane Rosenberg/Reuters
Sean "Diddy" Combs and his defense team pass notes during the cross examination of Casandra "Cassie" Ventura during Combs' sex trafficking trial in New York City, May 16, 2025 in this courtroom sketch. Jane Rosenberg/Reuters
 
 

For their fifth witness, prosecutors called Dawn Richard, a singer-songwriter who, in a civil lawsuit, has accused Combs of sexual assault, forced labor and forced imprisonment. A former member of the girl group Danity Kane, Richard allegedly witnessed multiple instances when Combs abused Ventura, including an incident she described in her testimony. Combs had broadly denied the allegations in that case.

Richard testified that she witnessed Combs beat Ventura in Los Angeles in 2009, describing how Combs had a violent outburst while Ventura tried to cook breakfast.

"He came downstairs angry. He said, 'Where the f---- is his eggs?'" Richard testified. "He took the skillet with the eggs" and took a swing at Ventura, adding that Ventura dropped to the ground, "literally trying to hide her face or her head."

After a series of objections, the judge adjourned court until Monday while he considers potentially striking portions of Richard's testimony.

 

Author: Aaron Katersky, Tonya Simpson, Josh Margolin, Kaitlyn Morris, and Peter Charalambous

Source: ABC GMA

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