The widely publicized trial of entertainment mogul Sean Combs began this week with testimony from a significant witness in the proceedings. Combs faces serious federal charges including racketeering and sex trafficking through means of coercion, allegations he has consistently denied.
Cassandra Ventura, professionally known as Cassie, spent three days providing testimony about her former relationship with the music executive. Her account included detailed descriptions of private gatherings she characterized as “freak-off” events and claims of physical mistreatment during their relationship.
As the proceedings continued, defense attorney Anna Estevao began her cross-examination, introducing electronic communications exchanged between the former couple throughout their eleven-year relationship. During this exchange, an unintended moment occurred when courtroom microphones captured Combs apparently expressing approval to his legal representative.
According to reports from the Daily Mail, the 55-year-old music producer was heard whispering that he was “proud” of his attorney’s questioning strategy, seemingly unaware that his comment would be audible within the New York courtroom.
This interaction occurred as Estevao presented messages that appeared to demonstrate Ventura’s affection toward Combs. The defense strategy appears focused on establishing that certain intimate encounters were consensual rather than coerced.
While testifying, Ventura had described participating in these gatherings unwillingly, characterizing them as “humiliating” and physically demanding. She recounted disturbing incidents, including one where Combs allegedly instructed a third party to engage in degrading acts. Ventura further testified about numerous physical health consequences she experienced and stated she later required trauma therapy for PTSD following the relationship’s conclusion.
During Thursday’s cross-examination, Estevao referenced a 2017 message allegedly sent by Ventura to Combs stating: “Please don’t play victim. That’s all you wanted and that’s why I was upset. I love our FOs [freak-offs] when we both want it.”
The attorney established through questioning that the relationship had contained mutual affection, with Ventura acknowledging that she had loved Combs and believed he had loved her. It was following this exchange that Combs apparently expressed satisfaction with his attorney’s approach.
Other significant testimony included Ventura’s claims regarding substance use, where she stated Combs struggled with opiate addiction and regularly consumed various recreational drugs. She described a 2012 incident at the Playboy Mansion where she alleged he experienced an overdose.
In an additional complexity to their relationship dynamic, Ventura testified that Combs occasionally expressed concern about her mental wellbeing, once suggesting medical consultation after observing possible effects from substance use.
The trial continues as both prosecution and defense present their cases before the court.