Cassie Ventura Continues Testimony in Sean Combs’ Trial

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Casandra “Cassie” Ventura took the witness stand Friday for what is expected to be the final day of her grueling, explicit four-day testimony in ex-boyfriend Sean “Diddy” Combs’ sex-trafficking and racketeering trial. 

Combs’ lawyer, Anna Estevao, picked up where she left off Thursday, asking Ventura about the notorious incident at the InterContinental Hotel in Los Angeles on March 5, 2016. Jurors have seen surveillance video of Combs grabbing, kicking, and dragging Ventura in the hotel’s hallway. Estevao suggested late Thursday that Ventura and Combs had consumed “a bad batch of MDMA” leading up to the violent attack.

In her first questions Friday, Estevao asked Ventura if she previously told investigators that Combs had blacked out that day. Ventura said he was intoxicated. The lawyer then had Ventura read a text message she sent to Combs a few days later, on March 10, 2016.

“When you get fucked up the wrong way you always want to show me that you have the power and you knock me around. I’m not a rag doll, I’m someone’s child,” the message, read aloud in court, said, according to CNN.

Ventura also testified about an incident that took place a few months later, in August 2016, telling jurors that Combs snatched her phone while they were riding in a car and took off running down a major boulevard in Los Angeles. She said Combs discovered she was dating a professional football player and used her phone to call the man, who was not identified in court. Ventura said her mother called police over the incident.

Estevao later grilled Ventura over an audio recording in which she was heard confronting a D.J. after the man said he saw an explicit video of Ventura. Ventura confirmed she was worried that a male escort, identified in court as Jonathan Oddi, had recorded her during a freak-off. In the audio recording, Ventura was heard threatening the D.J., saying, “I’m going to kill you, and then he’s gonna kill you again.”

Ventura’s mention of Oddi garnered immediate headlines. He was arrested in May 2018 for ranting against President Trump and opening fire on police at Trump’s National Doral golf club in Miami. He claimed a connection to Combs at the time, calling himself a “sex slave,” but the allegation received little traction back then.  

This week has been the first time the former celebrity couple has seen each other in years. Combs is on trial for the sex-trafficking of two women between 2009 and 2024, racketeering conspiracy stretching back to 2004, and transportation to engage in prostitution. He has pleaded not guilty and faces 15 years to life in prison if convicted as charged. 

Thursday’s proceedings were slow-paced, with Estevao establishing that Combs and Ventura fell quickly and deeply in love, exchanging hundreds of loving messages. Yet even in the first few months of their romance in 2007, emails show Ventura trying to voice her concern with Combs’ treatment of her. “I never seem to make the right decisions to you,” she wrote. “I hope to just be able to learn what it is you want in a woman and give it to you.”

Ventura readily admitted to a serious opiate addiction and feeling jealousy, especially early on, over Combs’ relationships with other women, including the mother of three his children, Kim Porter. 

She said that she would have done anything to keep Combs happy, including freak-offs. Combs’ lawyers displayed several text messages where Ventura agreed to participate in what she described as “humiliating” and “disgusting” sexual encounters, including a thread from 2009 where Ventura wrote, “I’m always ready to freak off lolol,” and “I just want it to be uncontrollable.”

On Thursday, Combs was animated during Ventura’s cross-examination, appearing somewhat frustrated with the slow pace his attorney was taking when quizzing Ventura, passing several notes to his legal team. He seemed more satisfied when Estevao read out the entire chain of texts that led up to the freak-off before Combs was seen on security footage attacking Ventura in the hotel hallway. He nodded when Estevao brought up a message from Ventura that read, “Baby, I want to [freak-off] so bad, but I don’t want to fuck myself up. What am I to do?” 

Ventura, the star witness for Southern District of New York prosecutors, herself seemed frustrated, answering just “yes” or “no” to confirm the texts were authentic without any opportunity to give added context. In that March 2016 message exchange, Combs repeatedly asked Ventura “what’s your plan” and was annoyed that Ventura wasn’t promptly replying to him. Ventura tried to explain that Combs was making it clear he wanted a freak-off, and she was trying to placate. She explained in prior testimony that Combs was volatile, and she was concerned he might do something ahead of her red carpet premiere for her 2016 movie, The Perfect Match.

Prosecutors questioned Ventura for one-and-a-half days, and there was considerable debate this week over how much time the defense would have to cross-examine. Combs’ lawyer Marc Agnifilo told the court that they might need until Monday, with prosecutors noting that Ventura, who is eight-and-a-half months pregnant, may go into labor imminently. 

“In what universe did you not understand that this was important given that it was in numerous filings and discussed among the parties several times?,” Judge Arun Subramanian asked Agnifilo on Thursday. “That this witness was going to be done this week.”

In a letter to the judge filed overnight, prosecutors accused the defense of trying to extend Ventura’s testimony into next week so they could review her transcripts over the weekend, “or risk a mistrial if the witness goes into labor.” They said the alleged “inefficiency of cross-examination” on Thursday “raises the inference that the defendant hopes to accomplish precisely that outcome.”