NEW YORK (AP) — R&B singer Cassie was forced under cross-examination Thursday to read aloud to a jury her explicit messages with former boyfriend Sean “Diddy” Combs, some of which showed her expressing enthusiasm for Combs-directed encounters with other men that she previously testified had disgusted her.
Combs’ lawyers began questioning the prosecution’s star witness on the fourth day of the music mogul’s sex trafficking trial in Manhattan, which is expected to last about two months. Federal prosecutors accuse Combs of exploiting his status as a powerful music executive and entrepreneur to violently force Cassie and other women to take part in these encounters with sex workers, which he called “freak-offs.”
Combs denies all the allegations and has pleaded not guilty. His lawyers are seeking to portray Cassie as a willing participate in Combs’ lifestyle, and say that while he could be violent, nothing he did amounted to a criminal enterprise. Defense attorney Anna Estevao read what Combs said in email and text exchanges, while Cassie recited what she wrote to him.
In one from August 2009, Combs asked her: “When do you want to freak off? Lol.”
“I’m always ready to freak off,” she replied.
Two days later, Cassie sent an explicit message to Combs.
“I can’t wait to watch you. I want you to get real hott,” he replied.
“Me Too, I just want it to be uncontrollable,” she said.
Cassie asked for a short break, which Judge Arun Subramanian granted, after yet more explicit messages were shown. This came a day after she was made to see still images from videos of sexual encounters during prosecutors’ questioning.
Prior to the start of the trial, Combs’ lawyers made clear that they intended to label a lot of the sexual behavior of their client as part of the swingers lifestyle.
Estevao asked Cassie directly whether she thought “freak-offs” were related to the swingers lifestyle. “In a sexual way,” Cassie responded, before adding: “They’re very different.”
The cross-examination had begun with gentil questioning by Estevao, as she had Cassie first read through warm and loving messages with Combs early in their relationship. Cassie testified that Combs was charismatic, with a larger-than-life personality. At the time, she said, “I had fallen in love with him and cared about him very much.”
Thursday’s testimony and evidence was in contrast to the violence and shame Cassie said accompanied “hundreds” of her encounters with male sex workers that Combs watched and controlled during their relationship — which stretched from 2007 to 2018 and started when she was 19 and he was in his 30s.
She said the drug-fueled “freak-offs” would last hours and even days, with her sometimes taking IV fluids to recover and eventually developing an opioid addiction because it made her “feel numb” afterwards.
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 testified Wednesday that Combs raped her when she broke up with him, and that he kept her locked in a life of physical abuse by threatening to release degrading sexual videos of her.
“I feared for my career. I feared for my family. It’s just embarrassing. It’s horrible and disgusting. No one should do that to anyone,” said Cassie, whose legal name is Casandra Ventura. The Associated Press does not typically name people who say they have been sexually abused unless they come forward publicly, as Cassie has.
Combs initially appeared relaxed as cross examination got underway Thursday, sitting back in his chair with his legs crossed and conferring with his attorney Marc Agnifilo. The courtroom was packed with family and friends of Combs, journalists and a row of spectator seats occupied by Cassie’s supporters.
Cassie 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.
Estevao asked Cassie if it was “fair to say” that Combs’ career was ruined after she sued him, making public for the first time the concept of “freak-offs.” Cassie responded, “I could understand that.”
Combs, 55, has been jailed since September. He faces at least 15 years in prison if convicted.
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Associated Press journalists Julie Walker in New York and Dave Collins in Hartford, Connecticut, contributed to this report.
