NEW YORK (AP) — R&B singer Cassie was pressed to read aloud her own explicit messages to ex-boyfriend Sean “Diddy” Combs in federal court Thursday, including texts that showed her expressing desire for the drug-fueled group sex she previously testified left her traumatized.
Lawyers for Combs sought to portray Cassie to the jury as a willing and eager participant in the music mogul's sexual lifestyle. Combs has pleaded not guilty to federal sex trafficking and racketeering charges. His defense says that, while he could be violent, nothing he did amounted to a criminal enterprise.
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FILE - Cassie Ventura, left, and Sean "Diddy" Combs, arrive at the Los Angeles premiere of "Can't Stop, Won't Stop: A Bad Boy Story" at the Writers Guild Theater, June 21, 2017, in Beverly Hills, Calif. (Photo by Chris Pizzello/Invision/AP File)
Cassie Ventura takes an oath before testifying in Manhattan federal court, Tuesday, May 13, 2025, in New York. (Elizabeth Williams via AP)
Sean Diddy'Combs, far left, and attorney Marc Agnifilo, right, sit at the defense table during witness testimony in Manhattan federal court, Tuesday, May 13, 2025, in New York. (Elizabeth Williams via AP)
FILE - Cassie Ventura, left, and Sean "Diddy" Combs appear at The Metropolitan Museum of Art's Costume Institute benefit gala celebrating "China: Through the Looking Glass" in New York on May 4, 2015. (Photo by Charles Sykes/Invision/AP, File)
Cassie Ventura wipes tears from her eye while testifying in Manhattan federal court, Tuesday, May 13, 2025, in New York. (Elizabeth Williams via AP)
Prosecutors say he exploited his status as a powerful music executive to violently force Cassie and other women into these marathon encounters with sex workers, called “freak-offs,” which sometimes lasted days. Combs insists all the sex was consensual. He's also accused of using his entourage and employees to facilitate illegal activities, including prostitution-related transportation and coercion, which is a key element of the federal charges.
Messages between Combs and Cassie — both romantic and lurid — were the focus of the fourth day of testimony in a Manhattan courtroom. Defense attorney Anna Estevao read what Combs wrote, while Cassie recited her own messages about what she wanted to do during the freak-offs. Cassie’s testimony will resume Friday.
Combs, 55, has been jailed since September. He faces at least 15 years in prison if convicted.
While Cassie, whose legal name is Casandra Ventura, has said she felt compelled to participate in freak-offs to keep Combs happy, Estevao pointed to message exchanges where Cassie appeared excited about the sexual encounters and raised the idea of having one on her own.
In August 2009, Combs asked when she wanted the next encounter to be, and she replied “I’m always ready to freak off.” Two days later, Cassie sent an explicit message and he replied in eager anticipation. She responded: “Me Too, I just want it to be uncontrollable.”
Later that year, however, she also sent Combs messages that she was frustrated with the state of their relationship and needed something more from him than sex.
Estevao also noted a July 2013 text message exchange where Cassie wrote to Combs, “Wish we could've FO'd before you left,” using the initials of freak-off.
In a 2017 text message, Cassie told Combs: “I love our FOs when we both want it." On the stand Thursday, Cassie explained: “I would say loving FOs were just words at that point.”
Cassie complained at one point that jurors weren’t hearing the full context of the messages the defense was highlighting, saying, “There’s a lot we skipped over.”
Combs’ attorney presented Cassie with sexual texts she sent before a 2016 encounter at a Los Angeles hotel, where Combs was caught on surveillance video kicking and dragging her in a hallway. Cassie said she wanted to get the encounter over with, in order to keep Combs happy and avoid a scene ahead of movie premier she was attending days later.
Estevao raised instances of Cassie's anger with Combs and her admitted jealousy over attention he gave other women. Cassie said Combs didn't want her seeing anyone else, but the same rules didn't apply to him.
Cassie testified that after a few years with Combs she longed to be a bigger part of his life but he wouldn’t let her in. Their relationship lasted from 2007 to 2018.
The cross-examination didn’t have the combative tone of a stereotypical defense grilling. Estevao spoke gently, and she and Cassie seemed like two friends chatting at times.
The 38-year-old Cassie — who is in the third trimester of pregnancy with her third child — has held up well on the witness stand. She cried several times during the previous two days of questions by the prosecution, but for the most part has remained composed and matter-of-fact as she spoke about the most sensitive subjects.
The Associated Press does not typically name people who say they have been sexually abused unless they come forward publicly, as Cassie has.
As the explicit messages were read, Combs appeared relaxed at the defense table, sitting back with his hands folded and legs crossed. The courtroom was packed with family and friends of Combs, journalists, and a row of spectator seats occupied by Cassie’s supporters including her husband.
During a break, Combs stood at the table, huddling with his lawyers, holding a pack of Post-It notes in one hand and a pen in the other. At one point, he turned to the gallery and acknowledged a few reporters who were studying his demeanor. “How you doing?” he asked. Combs' daughters were not in the courtroom Thursday.
Jurors leaned forward in their seats to follow along as the messages were displayed on monitors in front of them in the jury box. One woman shook her head as a particularly explicit message was shown. A man stared intently at the screen, pressing his thumb to his chin. Other jurors appeared curious and quizzical, some looking at Cassie or jotting notes.
While prosecutors have focused on Combs’ desire to see Cassie having sex with other men, she testified that she sometimes watched Combs have sex with other women. She said Combs described it as part of a “swingers lifestyle.”
Estevao asked Cassie directly whether she thought freak-offs were related to that lifestyle.
“In a sexual way,” Cassie responded, before adding: “They’re very different.”
Cassie said Tuesday that Combs was obsessed with a form of voyeurism where “he was controlling the whole situation.” The freak-offs took place in private, often in dark hotel rooms, unlike Combs’ very public parties that attracted A-list celebrities.
She testified she sometimes took IV fluids to recover from the encounters, and eventually developed an opioid addiction because it made her “feel numb” afterward.
Cassie’s testimony on cross-examination was in contrast to previous days, when she described the violence and shame that accompanied her “hundreds” of freak-offs during her relationship with Combs.
Cassie testified Wednesday that Combs raped her when she broke up with him in 2018, and had locked in a life of abuse by threatening to release videos of her during the freak-offs.
She sued Combs in 2023, accusing him of years of physical and sexual abuse. Within hours, the suit was settled for $20 million — a figure Cassie disclosed for the first time Wednesday — but dozens of similar legal claims followed from other women. It also touched off a law enforcement investigation into Combs that has culminated in this month's trial.
Associated Press journalists Julie Walker in New York and Dave Collins in Hartford, Connecticut, contributed to this report.
FILE - Cassie Ventura, left, and Sean "Diddy" Combs, arrive at the Los Angeles premiere of "Can't Stop, Won't Stop: A Bad Boy Story" at the Writers Guild Theater, June 21, 2017, in Beverly Hills, Calif. (Photo by Chris Pizzello/Invision/AP File)
Cassie Ventura takes an oath before testifying in Manhattan federal court, Tuesday, May 13, 2025, in New York. (Elizabeth Williams via AP)
Sean Diddy'Combs, far left, and attorney Marc Agnifilo, right, sit at the defense table during witness testimony in Manhattan federal court, Tuesday, May 13, 2025, in New York. (Elizabeth Williams via AP)
FILE - Cassie Ventura, left, and Sean "Diddy" Combs appear at The Metropolitan Museum of Art's Costume Institute benefit gala celebrating "China: Through the Looking Glass" in New York on May 4, 2015. (Photo by Charles Sykes/Invision/AP, File)
Cassie Ventura wipes tears from her eye while testifying in Manhattan federal court, Tuesday, May 13, 2025, in New York. (Elizabeth Williams via AP)
