Cassie discusses early career during cross-examination
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 went on to explain how when she signed on to Bad Boy Records, which Combs founded, she had a platonic relationship with 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.”
Courtroom turns tense after lawyers allege Diddy’s career was ‘ruined’
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.
Ventura Fine expressed concern to Combs about ‘freak offs’
In texts from December 2009, Ventura Fine told Combs that in order 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.
Who are Diddy’s lawyers? Anna Estevao presses Ventura Fine in cross-examination
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.
Lawyers read sexually explicit messages between Cassie, Diddy in court
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.
Combs’ lawyers hone in on jealousy angle in Ventura Fine cross-examination
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 previews bigger discussion on alleged ‘freak offs’
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.
Defense shows affectionate messages between Cassie, Diddy
Combs’ attorneys kicked off their cross-examination by displaying kind messages sent between Cassie 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 in 2023 ‘didn’t want to be alive anymore’
Ventura Fine in court testified that in early 2023, around the time before she went to rehab for opioid addiction and began trauma therapy, she experienced suicidal ideation.
“I was spinning out” at the time, Ventura Fine testified. “I didn’t want to be alive anymore at that point.”
She recalled a time when she went home to her husband Alex Fine and children, “I remember telling him, ‘You can do this without me.'” Ventura Fine said during testimony it all just felt “too painful” and that “I tried walking out the door into traffic and my husband wouldn’t let me.”
Cassie alleges Diddy raped her in 2018 after she met her now-husband Alex Fine
Another major revelation came from 2018, after Ventura Fine and Combs were no longer together and she had started dating her now-husband, Alex Fine. She said she and Combs met up for dinner, during which he was friendly and kind.
Afterward, he drove her back to her home and walked her inside. “And then he raped me in my living room,” Cassie alleged. She said she cried and told him “no” during the alleged rape.
Prosecutors asked how she felt in that moment: “It was like someone taking something from you.”
Cassie says Diddy attacked her after discovering Kid Cudi relationship
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.
These Diddy family members have been in court amid his sex-crimes trial
Several members of the embattled rap mogul’s family, including his adult children, have turned out in New York this week as his criminal trial gets underway.From stepson Quincy Brown to Combs’ biological sons and daughters and former partners, here’s a look at his loved ones who have been spotted at the courthouse.
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; 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 the Substance Abuse and Mental Health Services Administration‘s free and confidential treatment 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) and Hotline.RAINN.org and en Español RAINN.org/es.
This article originally appeared on USA TODAY: Diddy trial live updates: Courtroom turns tense as Combs’ lawyers question Cassie
