Attorneys for Sean “Diddy” Combs are honing in on his turbulent relationship with Cassie Ventura after harrowing testimony on the hip-hop mogul’s alleged abuse.
Cross-examination in Combs’ sweeping federal sex-crimes trial resumed in Manhattan court on May 16. Combs’ legal team grilled Casandra “Cassie” Ventura Fine on what lawyers have called her own history of domestic violence, as well as claims that she was motivated by money to get back at him.
Combs dated Ventura Fine in the mid-2000s, and their relationship spanned a decade. The two became involved professionally and sexually when Ventura Fine was 19 and Combs was 36.
Despite Ventura Fine’s allegations that Combs coerced her into participating in drug-fueled “freak-off” parties — dayslong sexual performances that federal prosecutors have accused Combs of orchestrating — Combs’ attorneys on May 15 attempted to paint a picture that Cassie was in control of her situation.
The defense showed emails and text messages from early in Combs and Ventura Fine’s relationship, where they professed love for each other and she sought more attention from him.
Combs, 55, was arrested in September 2024 on charges of sex trafficking, racketeering and transportation to engage in prostitution. He has pleaded not guilty to all charges.
Cassie reveals Diddy overdosed in 2012
During cross-examination, Combs’ lawyer, Anna Estevao, revealed he overdosed on painkillers in February 2012.
Estevao asked Ventura Fine if she recalled the overdose, and the woman placed the incident around the same time that pop icon Whitney Houston died (the singer died Feb. 11, 2012).
Ventura Fine recalled they had a “freak off” that night and had gone to a sex club in San Bernardino, California, and Combs had later thrown a party at the Playboy Mansion in Los Angeles, but she went home. She testified that Combs later overdosed on painkillers, and she took him to the hospital.
Cassie expressed concern to Diddy about ‘freak offs’
In texts from December 2009, Ventura Fine told Combs that for her to “be more open with the things I do in bed,” she needed to feel like “this is my husband and the only one who will see this side of me.”
She went on to write that the alleged “freak offs” were starting to make her “feel a little dirty,” adding that she was going “back and forth in my mind” about whether she wanted to do them.
Ventura Fine explained on the stand that the “freak offs” became “a very integral part” of their relationship early on, but she wanted to develop the relationship more. Combs’ attorneys argued this showed that she put deep thought into the “freak offs” and felt comfortable expressing her concerns to her then-partner. “At that time,” she clarified.
Lawyers read sexually explicit messages between Cassie, Diddy
Diddy’s lawyers read texts between the former couple in the early years of their relationship, including extremely explicit messages, in court. In messages from August 2009, the couple discussed plans for a “freak off.”
Combs wrote, “When do you want to freak off?” with Ventura Fine responding, “I’m always ready to freak off. Lolol.” He wrote, “You tell me the day, you choose.”
In more texts from 2009, the court saw sexually explicit messages between them. In one message, Ventura Fine expressed eagerness to have sex, with Combs responding, “I can’t wait to watch you. I want you to get real hot.” On another occasion, she texted Combs how she anticipated being positioned during sex.
Diddy’s lawyers hone in on jealousy angle
The defense repeatedly sought to paint Ventura Fine as a jealous ex-partner. “This is about nature of relationships,” attorney Marc Agnifilo said before she took the stand. “This is about jealousies.”
The defense said Combs needed someone to take care of him, and Ventura Fine was one of the only people who saw the “real” him. “You knew how special you were to him,” the defense said, to which Ventura Fine responded, “Sometimes.”
Combs’ lawyers noted that he lied to and cheated on Ventura Fine and let her down, but she “kept coming back to him for 11 years.” She paused before responding, “I wouldn’t use ‘coming back.’”
Ventura Fine said she was in love with Combs, a “charismatic, big personality that everybody really loved,” and described him as “sweet” and “caring” at times.
Cassie says she was jealous of Kim Porter, Combs’ former partner
Combs’ attorneys asked Ventura Fine about Kim Porter, Combs’ on-and-off partner from the 1990s into the 2000s. “Were you jealous of Ms. Porter?” Combs’ lawyer Anna Estevao asked. Cassie replied on the stand, “I had some jealousy, yes.”
Porter is the late model who died in 2018 of pneumonia, as well as the mother of four of Combs’ seven children.
Jurors saw a series of texts from Cassie from 2013 in which she said she was concerned she was looking like a “side piece” and not Combs’ partner. She was upset in the messages sent around the holidays, spurred by seeing Porter and Combs with their children and not being invited to family vacations and get-togethers.
Why is Diddy on trial?
Combs is facing federal sex-crimes and trafficking charges in a sprawling suit that has eroded his status as a power player and kingmaker in the entertainment industry.
He was arrested in September 2024 and has been charged with racketeering, sex trafficking and transportation to engage in prostitution. He has pleaded not guilty to all five counts.
What is racketeering?
Racketeering is the participation in an illegal scheme under the Racketeer Influenced and Corrupt Organizations Statute, or RICO, as a way for the U.S. government to prosecute organizations that contribute to criminal activity.
Using RICO law, which is typically aimed at targeting multi-person criminal organizations, prosecutors allege that Combs coerced victims, some of whom they say were sex workers, through intimidation and narcotics to participate in “freak offs” — sometimes dayslong sex performances that federal prosecutors claim they have video of.
Where can I watch the Diddy trial?
The trial will not be televised, as cameras are typically not allowed in federal criminal trial proceedings.
USA TODAY will be reporting live from the courtroom.
Contributing: USA TODAY staff
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