Cassie Describes the Pain Caused by Sean ‘Diddy’ Combs’ Cheating as Cross-Examination Starts at Trial

R&B singer Cassie discussed the pain caused by Sean “Diddy” Combs’ cheating during their tumultuous nearly 11-year relationship. This revelation came as Combs’ legal representatives began their cross-examination of the prosecution’s main witness in his sex trafficking trial on Thursday.

The testimony marked Cassie’s third day on the witness stand. Previously, over two days of questioning by prosecutors in a Manhattan court, the 38-year-old recounted how Combs allegedly raped her following their breakup in 2018 and had allegedly trapped her in an abusive relationship by threatening to expose compromising sexual videos.

Combs is accused of leveraging his influential role in the music industry to coerce Cassie and others into unwanted sexual situations. The charges against him include racketeering and sex trafficking through force, fraud, or coercion. More alleged victims are expected to testify.

Combs denies all of the allegations and has pleaded not guilty. His attorneys acknowledge he could be violent, but say the sex he and others engaged in was consensual and that nothing he did amounted to a criminal enterprise.

Defense attorney Anna Estevao began by questioning Cassie in a gentle tone of voice – notable because so many cross examinations begin with efforts to unsettle or agitate a witness. Estevao’s approach was the opposite.

“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.

Combs appeared relaxed as cross examination got underway, sitting back in his chair with his legs crossed and conferring with his attorney Marc Agnifilo.

The first exhibits introduced by Estevao were messages between Combs and Cassie in the early years of their relationship. In April 2010, Cassie told Combs: “Going to sleep now so it can be tomorrow faster and you can be home. Love you!!!” Combs replied: “Love my baby.”

The testimony stood in contrast to the violence, fear and “disgusting” sex acts Cassie testified about in her first days on the stand. Early Thursday, the judge denied a request by defense lawyers to introduce text communications between Combs and Cassie that would include references to specific sexual acts.

Defense lawyers have indicated that the cross examination will likely be finished by the end of Friday’s court session.

Cassie has held up well over two days of direct questioning by prosecutors. She cried several times but for the most part has remained composed and matter-of-fact as she talked about some of the most sensitive subjects imaginable, in a courtroom packed with family and friends of Combs, journalists and one row of spectator seats occupied by Cassie’s supporters. She is in the third trimester of pregnancy with her third child.

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.

Cassie also said she didn’t feel she could refuse Combs’ 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 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,” 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.

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.

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.