Attorneys forSean "Diddy" Combsare honing in on his turbulent relationship withCassie Venturaafterharrowing testimonyon the hip-hop mogul's alleged abuse. Cross-examination in Combs'sweeping federal sex-crimes trialresumed in Manhattan court on May 16. Combs' legal team grilledCasandra "Cassie" Ventura Fineon 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, wasarrested in September 2024on charges of sex trafficking, racketeering and transportation to engage in prostitution. He has pleaded not guilty to all charges. Diddy on trial newsletter:Step inside the courtroom as music mogul faces sex-crimes charges. Ventura Fine revealed that in 2024 she had gone to Willow House – an Arizona addiction treatment center – for rehab, where she had no phone as part of the facility's rules for her 45-day program.She also revealed she has been taking buprenorphine for opiate addiction since 2022. Ventura Fine said she wrote her book after treatment, and that while she began writing while at Willow House, "It wasn't really an idea."Ventura Fine confirmed that the center treats sex addiction, sexual compulsion and love addiction, but she was not treated for any of those during her stay. She said she received neurofeedback therapy, which involves putting an electrical device on her head. She said she "probably" did this five or six times, about once a week, while she was there, explaining she believed the therapy was meant "to help me with my trauma."She also didEMDR therapyduring her stay and said it was part of the trauma treatment to help her recount memories and process them. Some of the treatment involved reimagining a traumatic experience, which she likened to imagining walking out of a room if previously you were being beaten up in that room and couldn't leave. In November 2018, when Diddy's exKim Porter, who is the mother offour of Combs' seven children, died unexpectedly from pneumonia, Ventura Fine flew to Georgia and attended her memorial service. While there, Combs texted her asking why Ventura Fine left the service without saying goodbye. Ventura Fine responded, insisting that she did. "I know how crazy and painful all this is," Ventura Fine texted, but "you posted that Kim was your soulmate. What was the 11 years all about?" The defense asked whether Ventura Fine found that "extremely hurtful" and she said "yes." Ventura Fine never saw Combs again after that. He tried to get in touch through mutual friends, but she rebuffed his advances. As questioning continued, the defense tried to poke holes in the timeline of the Diddy's alleged rape of Cassie, as she noted in herNovember 2023 lawsuit. On Aug. 21, 2018, Combs texted Cassie, "I know I look bad to you. I didn't turn you on yesterday. I fell off.""You saw Mr. Combs the day before this message?" Estevao asked Ventura. A few days after, she texted back, "I'm so heartbroken." Combs responded, "Me too. Have a good night."The implication was that they had a breakup conversation within those few days. However defense attorneys said that in a November 2023 conversation with prosecutors, Ventura Fine said this incident occurred after Combs got home from Burning Man in September 2018.In the interview, she described going to dinner with Combs before the alleged rape; saying that he was "acting strangely" and that he "seemed anxious.""You told the prosecutors you didn't think Mr. Combs was in his right mind" because he wouldn't stop when she told him to, Estevao said. According to the defense, Ventura Fine told prosecutors in April 2025 that the rape occurred in August 2018, seemingly differing from what she told them a year and a half prior. Asked about what she said in her civil suit about the rape, Ventura Fine testified that they had dinner at an Italian restaurant before the alleged rape. She said she didn't remember if she said he "forced" himself into her home in the lawsuit. She was then asked if she wondered whether Combs was in a bipolar episode during the rape, and she confirmed that she did. Combs' lawyer asked about her feelings for Combs in September 2018, with her saying, "There were still feelings there." As for her feelings for Combs now, she said, "I don't hate him," and "I have love for the past and what it was." Dawn Richard, a former member of girl group Danity Kane, is expected to take the stand, according toNBC News. Richard worked with Combs beginning in the early 2000s, first on his MTV reality show "Making the Band," then with Danity Kane and later after the group disbanded with the musical trio Diddy – Dirty Money. In 2024,Richard sued Combsfor sexual assault and battery, sex trafficking, gender discrimination and copyright infringement. In the lawsuit, the former Combs-run Bad Boy Records artist accused him of inhumane working conditions, including deprivation of food and rest, false imprisonment and groping. In the same lawsuit, Richard claimed she once witnessed Combs assault Ventura Fine. Aubrey O'Daycould testify in Sean 'Diddy' Combs federal sex-crimes trial Richard's fellow Danity Kane alumAubrey O'Day, once a rising star in Combs' orbit, has been subpoenaed to testify in his trial, according to a person familiar with the situation but not authorized to speak publicly to USA TODAY. Combs formed Danity Kane with Aundrea Fimbres, D. Woods, Shannon Bex, Richard and O'Day. The pop group disbanded and reunited several times since their formation, most notably with O'Day being removed from the group in 2008, although she later returned. Later, O'Day became a fierce critic of her former boss and has publicly praised his ex-girlfriend Ventura Fine amid her testimony during the trial. In court May 16, jurors heard audio recorded by Ventura Fine at an unspecified date in which she threatens to have someone killed over videos they may have of a "freak off." Talking on the phone to someone she said had a video of her, she said: "The video of me touching myself is important to my life… You have it? Why won't you show me." "Where is it? You have it, or you don't have it?" she continued, asking the person who she was having sex with in the video and threatening to kill the person possessing the video. The argument continued to escalate with Ventura Fine saying she will cut him up and put him in the dirt, and claiming: "You don't understand. I will kill you because you're playing games with me. And it's not going to be blood on my hands. Someone else is going to do it." Asked whether Combs supported her in making sure that "freak off" videos wouldn't get released, she replied: "I would say for the most part, yeah." In another instance, Ventura Fine suspected that an escort named Jonathan Oddi was recording a "freak off." Ventura Fine said she told Combs about her suspicions, and Combs said, "I'll take care of it." "Had a sex video of you been released, that would have been embarrassing, right?" Combs' lawyer, Anna Estevao, asked. "For sure," Ventura Fine replied. In court, there were two instances discussed where Combs suspected Ventura Fine was cheating on him. "He found out you were dancing with another person in the entertainment industry? Do you remember the incident where he suspected you of dancing withChris Brown?" Estevao asked of a 2013 instance. Ventura Fine said she did not remember the incident, but she "was not dancing" with the singer. Estevao showed an exhibit to help jog Ventura Fine's memory, where Combs allegedly took the "Me & U" singer's phone after he suspected her of dancing with Brown. After looking at the evidence, Ventura Fine said, "It says that in the message, but I don't really remember it." Ventura Fine is close friends with Karrueche Tran, the actress and model who won a five-year restraining order against ex-boyfriend Brown in 2017. Michael B. Jordan, Dawn Richard,Lauren London and Mike Myers named in Diddy trial. Here's why There was another instance in August 2016 where Combs took Ventura Fine's phone when he suspected that she was dating someone else. Ventura Fine said, "At this point, we were not in a great place. I was dating someone else." But one day, while she was in a car with Combs, he asked her to unlock her phone to call her mom. When she unlocked her phone, he grabbed it and fled the vehicle. "There wasn't a fight. He was just gone," Ventura Fine said. "He was trying to get in it and read what was in my phone." A couple hours later, Ventura's mom called police because her daughter returned home with no phone. Then, the phone was eventually returned later that day. Estevao asked whether Combs went through Ventura Fine's phone and called someone. "I believe so. I wasn't there," Ventura Fine replied. "And that was a professional NFL player, right?" Estevao asked. "He was at the time. I don't know if he is now," Ventura Fine responded. Ventura Fine explained that she didn't consider it cheating and that Combs got very jealous and possessive when she started dating other people. "I don't know that I would call it cheating. When you're not with someone, it's not cheating. But that's a technicality in a boyfriend-girlfriend relationship," Ventura Fine said. As the defense team returned to the2016 hotel assault, they appeared intent on portraying Combs as heavily under the influence of drugs and alcohol. "You believe that Combs was blackout, right?" Comb's lawyer asked, reviewing text messages days after the incident in which the rapper wrote to Ventura Fine: "I'm so horny for you!!!" to which she responded, "You are? Why? What made you feel that way?" and "Not a good vibe." See the full Sean 'Diddy' Combsand Cassie hotel video On the stand, Ventura Fine said she found it "a little strange" that he would suggest having sex so shortly after the assault, adding sarcastically that her text about the vibe "makes sense." "We need a different vibe from Friday," she wrote in a text, to which Combs responded: "I don't even wanna do that again." She replied, "Lol, true." The court also saw photos Ventura Fine took of her face and enlarged lip after the incident. Estevao asked why Cassie took the photos, and Cassie responded that she didn't remember taking them. Sean 'Diddy' Combs overdosedin 2012 and was hospitalized, Cassie Ventura testifies In texts from December 2009,Ventura Fine told Combsthat 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 thealleged "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. Diddy's lawyers read texts between the former couple in the early years of their relationship, includingextremely explicit messages, in court. In messages from August 2009, the couple discussed plans for a "freak off." Combs wrote, "When do you want tofreak 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 topaint 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 himfor 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's harrowing testimony,the myth of 'mutual abuse' and what domestic violence really looks like Combs' attorneys asked Ventura Fine aboutKim 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 offour 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 seeingPorter and Combswith their children and not being invited to family vacations and get-togethers. Ventura Fine touched on a connection to actorMichael B. Jordanas 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, perFox 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.) 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 wasarrested in September 2024and has been charged with racketeering, sex trafficking and transportation to engage in prostitution. He haspleaded not guiltyto all five counts. Jurors were told in a questionnaire reviewed by USA TODAY, "The trial is expected to last about eight weeks." 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 This article originally appeared on USA TODAY:Diddy trial updates: Attorneys grill Cassie on jealousy, threats
