Editor’s note: This page reflects the news from Sean “Diddy” Combs’ trial on Thursday, May 15. For the latest updates from Diddy’s trial, read USA TODAY’s live coverage for Friday, May 16.
This story contains graphic descriptions that some readers may find disturbing.
Sean “Diddy” Combs’ lawyers cross-examined his former girlfriend, singer Casandra “Cassie” Ventura Fine, following two days of her emotional testimony on his alleged physical, sexual and psychological abuse.
Combs’ federal sex-crimes trial resumed in Manhattan on May 15, and the one-time mogul’s lawyers continued asking Cassie about what they have called her own history of domestic violence. The rapper’s lawyers have also alleged she was motivated by money to get back at him.
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. “I wanted to spend so much time with him, at this point in 2010, because I’d fallen in love with him and I cared about him very much,” Ventura Fine told jurors.
As the court day wrapped, Combs’ legal defense team attempted to paint a picture of a Ventura Fine that was in control of her situation.
Ventura Fine’s testimony comes a year after CNN released 2016 surveillance video that showed Combs kicking, hitting and dragging the woman during an altercation at a Los Angeles-area hotel. Combs apologized for his violent behavior soon after the video’s release.
In court, Ventura Fine said Combs repeatedly threatened to release videos of her participating in his alleged drug-fueled “freak offs.”
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.
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 Ventura placed the incident around the same time that 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.
Ventura Fine also revealed they both tried to stop using drugs at times in their relationship, but rehab didn’t feel like it was possible for them. Sometimes they called each other “get-high” partners. She also said she believed Combs didn’t like it when she used drugs − unless it was with him.
If Combs learned she was doing drugs with others, Ventura Fine told the court he would turn “pretty explosive.”
Ventura Fine shed more light on an alleged confrontation between Combs and his long-time hip-hop rival Marion “Suge” Knight.
During court testimony on May 13, Ventura Fine recalled an alleged incident in which Combs left his house amid one “freak off” in Los Angeles after being tipped off by a bodyguard that Knight was at a diner nearby. In response, Ventura Fine reportedly told Combs, “Please don’t do anything stupid,” as she stayed behind.
Combs’ attorneys challenged Ventura Fine’s account, citing an alleged conversation she had with prosecutors in June 2024, during which she said she remembered “being brought along in a car and crying” when Combs and “D-Roc” reportedly went to Mel’s Diner to confront Knight.
When asked about the discrepancy in her recollection of the alleged event, Ventura Fine said, “It could be a misunderstanding because that never happened.”
Ventura Fine touched on a connection to actor Michael B. Jordan as Combs’ attorneys scrutinized Cassie’s other relationships.
Ventura Fine said Combs suspected that she was in a relationship with the Emmy-nominated actor after the pair broke up in 2015, per Fox News. At the time of their split, the singer-actress was filming a movie in South Africa (Cassie starred in the musical drama “Honey 3: Dare to Dance,” which was set in South Africa and reportedly concluded filming in December 2015.)
When asked about Combs’ reaction to an alleged relationship with Jordan, Ventura Fine said she “wasn’t there to see it,” according to NBC News, but added that Combs attempted to get in contact with her.
Combs’ attorneys asked Cassie 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 mom 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. Cassie 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.
Combs helped raise Quincy Brown, 33, Porter‘s son. He and Porter also had three other biological children together: son Christian Combs, 27, and twin daughters D’Lila and Jessie Combs, 17.
The defense asked: “You didn’t just want to be part of someone’s sexual fantasy?” to which Cassie responded, “No.”
The back-and-forth came as Combs’ defense lawyers have spent much of the day pointing to examples of Ventura Fine appearing to freely express concerns in their relationship, from managing their travel to sexual habits at times.
Ventura Fine spoke further about her relationship with rapper Kid Cudi, whose real name is Scott Mescudi, during cross-examination.
She said that she obtained a burner phone specifically for the purpose of her relationship with Mescudi, which began in 2011. Combs introduced the two and thought a musical collaboration would be good for her career. At that time, Ventura Fine said she was on a break with Combs but didn’t want to tell him that she was seeing Mescudi.
“I thought it would be way too dangerous to tell him about that,” she alleged. “He had a temper.”
Ventura Fine also testified that she continued to have “freak offs” while on a break with Combs because “it was a job.”
Combs’ lawyers asked Ventura Fine to describe her early career when she and Diddy first met. She said Combs and fellow celebrities Dallas Austin and Britney Spears all attended her 21st birthday party.
One of Diddy’s lawyers, Anna Estevao, pointed out that her first album did well, and she had recognizable songs. “You’re very beautiful and charming,” Estavao said, and Ventura Fine replied, “Thank you,” smiling.
“It’s true,” Estevao said, to laughter in the courtroom.
Ventura Fine explained how when she signed on to Bad Boy Records, which Combs founded, she had a platonic relationship with the rapper. After describing a tough performance on the program “106 & Park,” she said Combs came to her aid and supported her.
Estevao also pulled up an email from 2007, in which Ventura Fine said Combs is “constantly weary of me” and described herself as “sneaky,” “needy” and “a spoiled brat.” “I hate that you think I’m a malicious person,” Ventura Fine wrote, adding, “You just don’t think I’m the right one.”
The courtroom became tense when defense attorneys questioned Ventura Fine over the effect of her 2023 lawsuit on Combs’ career. When lawyers asked what happened to Combs’ career after she filed the case, Ventura Fine paused and said, “That’s a lot.”
“Is it fair to say his career was ruined?” a lawyer for the defense said, at which point prosecutors rapidly jumped in with objections, which the judge approved.
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.
“Do you recall having conversations with Mr. Combs about the swingers lifestyle?” Estevao later asked, to which Ventura Fine responded, “Yeah.” She went on to say the conversations were mainly about protocol, including how you act, and that some see it as a taboo topic.
The exchange offered a preview of what is expected to be one of the defense team’s main arguments – that while unconventional, Combs was a “swinger” and not a sexual abuser.
Nicole Westmoreland of Westmoreland Law LLC is the latest lawyer to join Combs’ legal team after filing a notice of attorney appearance with the court on May 6.
Combs’ defense team was already led by attorneys Marc Agnifilo and Teny Geragos. Both are founding partners at Agnifilo Intrater. Geragos is “particularly experienced in defending and investigating allegations of sexual misconduct,” according to the firm’s website.
Brian Steel, who represented Young Thug in the rapper’s RICO trial, is also working with Combs, as are attorneys Alexandra Shapiro, Xavier R. Donaldson, Anna Maria Estevao and Jason Driscoll.
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.
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.
Recalling the “early stages” of her relationship with Combs, Ventura Fine said she spent a lot of time feeling hurt. In texts from April 2010, she wrote: “So you hung up… It’s like I need … I haven’t seen you at all.”
She testified that she was worried she would lose him if she didn’t have sex with him the way he wanted. When asked whether she told him she wanted to do “freak offs” to make him happy, she responded, “No, there’s a lot more to that.”
“I’m sure we’ll get to that,” the defense attorney replied.
Combs’ attorneys kicked off their cross-examination by displaying kind messages sent between Ventura Fine and Diddy early in their relationship.
“I’m truly a lucky man. I love you, I miss you,” Combs wrote in one email shown during cross-examination. She emailed back saying that she was a lucky woman. In another text from 2009, Combs wrote, “I love sooooo much it makes me cry,” to which she responded “You hungry, pop pop?”
Ventura Fine was previously asked by prosecutors about her and Combs’ nicknames for each other. Ventura Fine revealed Combs called her “BG” for baby girl and “CC,” which stood for Cassie Combs. Her nickname for him was “pop pop,” which he decided on after asking what she called her grandfather.
In another text exchange, from a little over two years into their relationship, Combs wrote: “I love you so much it consumes my life. I never knew it could be like this.” A text from the same year from Ventura fine read: “Pop pop, I really miss you.”
When the defense asked how often they saw each other, Ventura Fine said there were long breaks between seeing one another since they both traveled for work.
Cassie testified about her brief relationship with rapper Kid Cudi in 2011, which began after they started working together on music.
Ventura Fine said she didn’t initially tell Combs about Cudi, whose real name is Scott Mescudi, but Combs went through her phone during a “freak off” and found out about the relationship.
He allegedly became enraged after he saw the emails, lunging at Cassie with a wine bottle opener between his fingers, she testified. As she left Combs’ house, Ventura Fine said the rapper kicked her in the back. When she got back to her hotel room, someone had urinated on the floor, knocked over the furniture and defecated in the toilet without flushing it.
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.
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.
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; Reuters
This article discusses suicide and suicidal ideation. If you or someone you know is struggling or in crisis, help is available. Call or text 988 or chat at 988lifeline.org.
If you or someone you know is struggling with mental and/or substance use disorders, you can call theSubstance Abuse and Mental Health Services Administration‘s free and confidentialtreatment referral and information service at 1-800-662-HELP (4357). It’s available 24/7 in English and Spanish (TTY: 1-800-487-4889).
If you are a survivor of sexual assault, RAINN offers support through the National Sexual Assault Hotline at 800.656.HOPE (4673) andHotline.RAINN.org and en EspañolRAINN.org/es.
