After being questioned by prosecutors for two days, Casandra Ventura Fine, known professionally as "Cassie," was cross-examined by Sean "Diddy" Combs' defense team during the fourth day of his federal sex trafficking trial in New York City.
Combs' lawyers have said they plan to focus on infidelity in the relationship when questioning Cassie, but the first day of their cross-examination focused on communications between the former couple and the regular illicit drug use that Cassie has previously testified about.
The 55-year-old music mogul faces a life sentence for charges of sex trafficking, transportation to engage in prostitution and racketeering. He has pleaded not guilty.
Cassie, 38, and Combs dated for over a decade. The pair met when she was 19 and he was 37. The singer was signed to his record label, Bad Boy Records.
Their tumultuous relationship ended in 2018 after years of alleged physical, sexual and psychological abuse.
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The prosecution is alleging that Combs used his money and power to orchestrate an empire of exploitation. Cassie has been a key witness for prosecutors, spending most of her testimony painting Combs as an abusive and controlling lover who allegedly coerced her into "hundreds" of marathon sex parties with drugs and male sex workers — referred to as "freak offs" — and filmed them.
Cassie claimed he threatened to publicize the videos and threatened the lives of the people around her whenever she tried to leave. She also testified that his staff members aided him in controlling her every move.
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Combs' lawyers acknowledge that he may have been violent at times, but insist sexual acts were consensual.
During the first part of the defense team's questioning of Cassie, The Associated Press said they had her read aloud texts and emails between her and Combs that were intended to portray Cassie as a willing participant in the "freak offs."
Some of the messages were sexually explicit in nature and The Associated Press reported that she appeared to be uncomfortable reading them out loud at times.
The defense team is trying to highlight the notorious "freak-offs" as more of a swingers lifestyle than orchestrated or forced sex acts, and had Cassie acknowledge that she also watched Combs have sex with other women.
Towards the end of the court day, the defense team asked Cassie more questions about her and Combs' drug use throughout their relationship.
Cassie has previously stated she took various types of drugs to "feel numb" during the "freak off" sessions, including ketamine, ecstasy, MDMA and even said she developed an opioid addiction.
On Thursday, Cassie told the court about a time where Combs allegedly overdosed on painkillers in 2012. Cassie said they had a "freak off" and went to a sex club before Combs went to a party at the Playboy Mansion.
Cassie told the defense attorney, Anne Estevao, that she took Combs to the hospital later that night. Estevao had a line of questions suggested Combs was dependent on opioids and withdrawals would make him upset.
Estevao had Cassie confirm during part of her testimony on Thursday that the excessive amount of baby oil used during "freak offs" was never laced with any drugs.
Cassie previously alleged in a lawsuit filed in 2023 that Combs raped her when she tried to leave him and often punched, kicked and beat her. The lawsuit was quickly settled with Combs paying $20 million to Cassie, a number that wasn't disclosed until her testimony on Wednesday.
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Cassie's husband, Alex Fine, has been present for most of her testimony. She is over eight months pregnant with the couple's third child.
Six out of seven of Combs' children and his mother have been at the trial each day, but his teenage daughters have been notably missing during the last two days of Cassie's testimony.
