WARNING: This story may affect those who have experienced sexual violence or know someone affected by it.
R&B singer Cassie faced cross-examination on Thursday in the Sean (Diddy) Combs sex trafficking trial and was forced to read aloud to a jury her explicit messages with former boyfriend Combs, some of which appeared to show her expressing enthusiasm for Combs-directed encounters with other men that she previously testified had disgusted her.
It was the third day on the stand for the 38-year-old Cassie, whose legal name is Casandra Ventura, after two days of questioning by prosecutors in a New York courtroom.
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 multi-day, drug-fuelled sex parties he orchestrated and called “freak-offs.”
He is charged with crimes including racketeering and sex trafficking by force, fraud or coercion. Several other accusers are set to testify.
Combs denies all the allegations and has pleaded not guilty. His lawyers are seeking to portray Cassie as a willing participate in Combs’s lifestyle, and say that while he could be violent, nothing he did amounted to a criminal enterprise.
Defence 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 [sic],” 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 more explicit messages were shown.
An 11-year relationship
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’s lawyers made it clear they intended to label a lot of the sexual behaviour 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.”
WARNING: Video contains disturbing details | Singer Cassie Ventura gave her second day of testimony as the prosecution’s key witness in the sex-trafficking trial of Sean ‘Diddy’ Combs — detailing years of rape, blackmail and physical abuse.
The cross-examination had begun with gentle questioning by Estevao, as she had Cassie first read through warm and loving messages with Combs early in their relationship.
“You and Sean Combs were in love for 11 years. You loved him and believed that he loved you as well,” Estevao said.
The attorney said Cassie’s love explained “why it hurt so badly when he lied…. When he cheated on you.” Cassie responded “yes” to both.
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 late 30s.
She said the drug-fuelled “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 now 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.
Combs initially appeared relaxed as cross-examination got underway on 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 on Wednesday — but dozens of similar legal claims followed from other women.
Estevao asked Cassie if it was “fair to say” that Combs’s career was ruined after she sued him, making public for the first time the concept of freak-offs.
Cassie responded, “I could understand that.”
WARNING: Video contains disturbing details | Cassie Ventura, Sean ‘Diddy’ Combs’s ex-girlfriend, testified at length at the music mogul’s sex-trafficking trial in New York about the alleged abuse she suffered, including graphic details of being coerced into ‘freak-off’ sex parties.
‘I feared for my career’
Cassie said Wednesday that Combs forced his way into her Los Angeles apartment and raped her on the living room floor after she said she was ending their relationship in 2018.
Cassie also said she didn’t feel she could refuse Combs’s demands for her to have “hundreds” of encounters with male sex workers — which he watched and controlled for hours and even days — because he would make her “look like a slut” if he made the “freak-off” videos public.
“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,” she said in her testimony on Wednesday.
She sued Combs in 2023, accusing him of years of physical and sexual abuse. Within hours, the suit was settled for $20 million US — a figure Cassie disclosed for the first time on Wednesday — but dozens of similar legal claims followed from other women.
Combs, 55, has been jailed since September. He faces at least 15 years in prison if convicted. The trial is expected to last about two months.
Defence lawyers have indicated the cross-examination will likely be finished by the end of Friday’s court session.
Support is available for anyone who has been sexually assaulted. You can access crisis lines and local support services through this Government of Canada website or the Ending Violence Association of Canada database. If you’re in immediate danger or fear for your safety or that of others around you, please call 911.
