Day four of the federal trial against Sean “Diddy” Combs took a dramatic turn Thursday as his former partner, singer Cassandra “Cassie” Ventura, faced her first cross-examination. The courtroom in New York heard Ventura recount years of alleged abuse, drug use, and coerced group sex acts what she called “freak-offs” under Combs’ direction. She described her experience as both traumatic and manipulative, alleging that violence followed any refusal to participate.
Combs’ legal team, led by Anna Estevao, countered with a strategy aimed at framing the relationship as consensual. The defense referenced intimate text messages between the two, suggesting Ventura had not only agreed to but helped plan some of the encounters. In those messages, Ventura appeared to express excitement about the events, including choosing rooms and escorts. Estevao’s line of questioning sought to reframe Ventura’s testimony as inconsistent with her written communications.
Ventura, however, pushed back strongly. She described the texts as “just words,” explaining she often went along with Combs’ demands out of fear. She said the so called “freak-offs” felt like a job she couldn’t escape and that her attempts to manage the situation were survival tactics. Ventura emphasized that while she once loved Combs and tried to make him happy, the trauma dominated her daily life either enduring the events or recovering from them.
The trial also addressed the 2016 hotel assault captured in a video released by CNN last year. In it, Combs is seen violently attacking Ventura. While the defense didn’t deny the incident, they did try to argue that Combs’ mental state and drug use should be considered. Ventura testified that drug use was frequent in their relationship, and while Combs occasionally tried to quit, he never sought professional rehab. She said he often displayed withdrawal symptoms, but couldn’t confirm his condition during the hotel incident.
Finally, the defense tried to shift the narrative to jealousy and relationship dynamics. They suggested that Ventura was frustrated with not being Combs’ “main girlfriend,” referencing his ongoing relationship with the late Kim Porter. Ventura responded that she never felt part of a real family during their 11-year relationship.
She also revealed that Combs reacted violently to her brief relationship with rapper Kid Cudi, who later claimed his car exploded in his driveway while seeing Ventura. The trial continues, with more testimony expected to shed light on one of the most high profile abuse cases in hip-hop.
