Sean ‘Diddy’ Combs’ Lawyer Cross-Examines Cassie Ventura

⚠️ This article contains graphic descriptions of sexual and physical violence.

On the fourth day of the federal sex trafficking and racketeering trial in New York, Cassandra “Cassie” Ventura resumed her testimony against music mogul Sean “Diddy” Combs, offering graphic accounts of their relationship, including coerced group sex, routine drug use, and emotional manipulation. The high-profile trial took a sharper turn Thursday as Combs' legal team cross-examined Ventura for the first time.

Defense Cites Texts Allegedly Supporting Consent

During cross-examination, Combs’ attorney Anna Estevao presented text messages suggesting Ventura’s participation in what she previously described as non-consensual "freak-offs"—events where she was allegedly directed to consume drugs and engage in sex acts with male escorts while Combs watched.

Messages presented in court included Ventura expressing anticipation and enthusiasm for these encounters, writing that she was “always ready to FO” and enjoyed them “when we both want it.” The texts also show Ventura coordinating logistics such as selecting rooms and hiring escorts. Ventura dismissed the texts as “just words,” insisting they didn’t reflect her true feelings.

Earlier in the trial, Ventura claimed she would often initiate or cooperate with the acts out of fear, trying to minimize harm by knowing when and how they would occur. She said she spent much of her time either participating in these “freak-offs” or recovering from them, adding that Combs turned violent when she resisted. “It felt like a job,” Ventura testified. “I hated them, especially when he recorded them.”

Substance Abuse and Withdrawals Raised in Defense

Estevao also questioned Ventura about Combs’ behavior during his alleged violent episodes, implying that substance withdrawal may have influenced his state of mind. Ventura confirmed their heavy drug use throughout the relationship, noting Combs made efforts to quit at times, though never through formal rehabilitation. She acknowledged his irritability during withdrawal but said she couldn’t confirm if he was under the influence during a 2016 hotel incident—footage of which, released last year, shows Combs assaulting Ventura.

Jealousy, Infidelity, and Power Imbalance Highlighted

The defense continued its strategy of reframing the case as one rooted in jealousy and personal conflict. Estevao referenced Ventura’s past frustrations over not being publicly acknowledged as Combs’ partner, especially during his ongoing relationship with Kim Porter, the mother of several of his children. The attorney also suggested Ventura was upset over not being Combs’ “main girlfriend,” referencing complaints she made during their 11-year relationship.

In response, Ventura said she never felt like part of Combs’ family despite his seven children and that while she was expected to remain loyal, Combs was not held to the same standard. She recounted dating rapper Kid Cudi during one of their breakups, but ending it after Combs allegedly began issuing threats. Notably, Kid Cudi’s car exploded in his driveway during that period—an incident he later referenced in a 2023 interview with The New York Times.

The Bigger Picture

Combs is currently facing charges of sex trafficking, racketeering conspiracy, and transportation for prostitution. While the defense denies any criminal wrongdoing, it has acknowledged Combs’ violent conduct in a past incident. The trial continues to reveal disturbing insights into the alleged power dynamics and abuse behind the public image of one of hip-hop’s most influential figures.