Defense cross-examines Cassie Ventura on her 11-year relationship with Sean ‘Diddy’ Combs

On Thursday, singer Casandra "Cassie" Ventura, ex-girlfriend of Sean "Diddy" Combs, returned to the stand on the third day of the federal criminal trial against the hip-hop mogul in New York.

Combs faces felony charges, including conspiracy to commit racketeering, sex trafficking and transportation for prostitution, to which he has pleaded not guilty.

Ventura, considered a key prosecution witness, continued her testimony under intense cross-examination by the defense, which is expected to extend through Friday.

Her account of her 11-year relationship with Combs, including the controversial events dubbed "Freak Offs," has captured the attention of the jury and the public.

Cassie Ventura on the stand

Ventura, 38 and pregnant with her third child, has been the center of attention since her testimony began on Tuesday, May 13. During the first two days, she described a relationship marked by control, violence and coercion.

She recounted, for example, how Combs, who was her boss at Bad Boy Records and later her partner, introduced her to "Freak Offs" when she was 22, events that became a weekly "job" that consumed her life.

Ventura also accused Combs of physically assaulting her, including an attack captured on video at a Los Angeles hotel in 2016, and raping her in 2018 following the end of their relationship.

The defense

The defense, led by attorney Anna Estevao, focused on cross-examination, seeking to highlight the complexity of Ventura's relationship with Combs and challenge the coercion narrative presented by the prosecution.

The jury examined emails and text messages between the couple, some of a sexually explicit nature, which revealed both moments of affection and discussions about the "Freak Offs."

Falling in love with Combs

Ventura confirmed that her relationship with Combs lasted 11 years, from 2006 to 2018, and that she was deeply in love with his "true personality." "I loved him and believed he loved me," she testified.

When asked by the defense whether her desire to please Combs included participating in the "Freak Offs," Ventura replied, “There’s a lot more to that," suggesting that her participation was not simply a matter of enthusiastic consent, but part of a more complicated dynamic influenced by Combs' control.

Messages

The defense presented text messages from 2009 that, according to Ventura, reflected "open communication" with Combs. In one of them, Ventura wrote, “I'm always ready to 'freak-off' lol” although she clarified that those words did not reflect her true feelings.

In other messages, she expressed feeling “dirty and grimy” after a Freak Off and needing to "feel safe" to be more sexually open. Ventura also asked Combs if he had "any more pills," admitting to using opiates like Norco and drugs like MDMA along with him.

The defense attempted to show these exchanges as evidence of his willingness to participate in the "Freak Offs," but Ventura insisted that he did not want Combs' staff to know about these events and never discussed them with friends, suggesting a desire for privacy or embarrassment.

Ventura distinguished "Freak Offs" from the "swinger lifestyle," explaining that, although she visited swingers' clubs with Combs, the events organized by him were "very different." She testified that Combs controlled every detail, from the lighting to her appearance (white nails and specific lingerie, among other things), and that sessions could last anywhere from 36 hours to four days, leaving her physically and emotionally drained.

Combs: a control freak

Ventura reiterated that Combs exercised strict control over her life, from her clothing to her social interactions. She confirmed that he would call her insistently if she did not answer the phone and that any action that upset him could trigger intense reactions.

Previous relationship

Ventura also spoke about her past, revealing that she met Combs through music producer Ryan Leslie, whom she dated for three years.

Leslie, about 10 years her senior, was her first significant relationship before Combs, who was also considerably older.

Implications and what's next

Ventura's cross-examination, which is expected to conclude Friday due to her advanced pregnancy, is crucial for both sides.

The prosecution seeks to establish that the "Freak Offs" were part of a criminal enterprise involving coercion and sex trafficking, while the defense argues that Combs' actions were consensual and do not constitute federal crimes.

The jury, composed of eight men and four women, must assess Ventura's credibility and the evidence, which includes videos, photos and messages, to determine whether the allegations against Combs hold up.

Jury dismissed for the day

After an intense day, the jury has been sent home for the day. Testimony is expected to resume tomorrow morning.