Cassie Said Diddy Made Her Feel ‘Just Like Dirt’

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When Sean “Diddy” Combs’s defense grilled Casandra “Cassie” Ventura on her abuse allegations at his sex-trafficking trial on Friday, the fallen music mogul seemed transfixed by this questioning. Combs, sporting an oatmeal-toned sweater and khaki slacks, could be seen moving his head up and down repeatedly, in slight nods, as he watched defense attorney Anna Estevao trying to cast doubt on Cassie’s timeline of events around the alleged August 2018 rape. Estevao noted that Cassie’s late 2023 lawsuit against Diddy put the attack in September 2018. 

Estevao also noted that Cassie told jurors that Diddy’s behavior at a dinner before the alleged attack seemed normal — but had previously told authorities that he was acting strange that night, speculating this could be “attributed to his bipolar disorder.” She also pointed out that Cassie had told prosecutors that he didn’t seem to be in his right mind “because he didn’t respond when you told him to stop.” Toward the end of her time on the stand, Cassie had an opportunity to emphasize just how much damage Diddy had wrought on her life, saying if she never got drawn into his world of extreme fetishes, she would have “autonomy and agency.” 

The defense attorney suggested that Cassie’s rape allegation stemmed from a complicated quarrel playing out as their decade-plus relationship came to an end. One late August 2018 message from Cassie to Diddy said “hit me when you can” with a heart emoji. Combs said he was in an investor meeting but asked “you good?” He then tried to call, but his call went to voicemail. “I know I look bad to you. I could tell I didn’t turn you on yesterday,” Combs said in another message. “I feel off. But I’m about to get my shit together.” 

Estevao’s message was clear as her second day of cross continued, and relied heavily on age-old rape myths — that Cassie couldn’t have been assaulted because she remained in contact with Diddy. That Cassie didn’t have enough ill will toward him to be a victim. That Cassie saw him again after the alleged attack. 

“You don’t still hate him?” Estevao asked. 

“I don’t hate him.” 

“In fact, you still have love for him?” 

“I have love for the past, for what it was.” 

Estevao asked Cassie about amicable, sometimes affectionate, exchanges between Cassie and Diddy after late August 2018. Did Cassie and Diddy meet up in late September? Cassie answered “yes.” “Did you have sexual intercourse with him?” Estevao asked. “I did,” Cassie said. During this encounter, did Cassie receive a FaceTime call from Alex Fine — her now-husband whom she was dating at the time? Cassie answered in the affirmative. 

“Did you answer that call?” Estevao pressed. 

“No,” Cassie responded. 

Cassie said that Fine found out that she slept with Diddy, and she also told him that Diddy had raped her. Estevao asked whether Fine “punched a wall.” Cassie said, “I believe so.” 

Throughout cross-examination, the heavily pregnant Cassie stayed cool and composed during cross. Her menswear-inspired suit complemented her no-nonsense comportment on the stand. 

During redirect, when prosecutor Emily Johnson had the opportunity to question Cassie, she sought to dispel Estevao’s attempt at tarring her character. Johnson asked about the $20 million settlement Diddy paid to end her lawsuit, which his defense has used to suggest that Cassie’s allegations were motivated by greed. “Would you give that money back if you never had to have Freak Offs?” Johnson asked. “If I never had to have Freak Offs, I would have agency and autonomy. I wouldn’t have to have worked so hard to get it back,” Cassie said, grabbing a tissue. When Johnson asked if Diddy beat her during Freak Offs, Cassie broke into tears. “How did you feel during the Freak Offs when Sean beat you?” Johnson asked. “Worthless, just like dirt, like I didn’t matter to him.” 

Earlier in the day, Estevao pushed back on notions that Diddy controlled Cassie with blackmail material from Freak Offs, suggesting at his sex-trafficking trial that the rapper had just as much to lose if intimate videos of their encounters with male escorts got released. 

“I will kill you, and I will hide you, and I will cut you up, and I will put you in the fucking dirt right now,” Cassie said in evidence presented by the defense. The sharp-tongued comment emerged during her second day of cross-examination. Diddy attorney Anna Estevao played an audio recording of Cassie and an associate from 2014 following a party she hosted in Atlantic City. This associate said he had seen a compromising video of Cassie, but then backtracked. “You’re fucking with me. I’m going to fuck you up,” Cassie also said in the recording. “It’s not going to be blood on my hands — someone else is going to do it.” 

Estevao tried to establish that Diddy didn’t want sex tapes to get out. She asked Cassie: What happened when you told him about concerns someone was recording them? “He said I’ll take care of it,” Cassie said. “These would have been embarrassing to him if they had been released?” Estevao asked. Cassie answered in the affirmative. 

Estevao suggested that Diddy’s concerns were all the more heightened because of his celebrity — and notoriety of an escort they had used. She asked about Cowboys4Angels, an agency that provided them male escorts and some of whom wound up participating in a reality-TV show on Showtime called Gigolos. Did an escort they had invited to a Freak Off appear on the show? “I’ve never seen the show, so I don’t know,” Cassie said. But she and Diddy wanted to keep their activities private? “Yes.” 

Casandra “Cassie” Ventura enters her fourth day of testimony in Sean “Diddy” Combs Manhattan federal court sex-trafficking trial on Friday — with an expectation his defense will continue to claim that she was a more than willing participant in his sexual demands. On Thursday, defense attorney Anna Estevao showed jurors numerous written exchanges between Diddy and Cassie to undermine the singer’s claims that he forced her into Freak Offs. One message from Cassie, for example, read: “I’m always ready to freak off. LOLOL.” 

Estevao also asked Cassie about her relationship with Kid Cudi. Prosecutors have contended that Diddy’s threat to blow up Kid Cudi’s car was among many acts of violence bolstering their racketeering case against him. Diddy’s defense tried to reframe the dispute with Kid Cudi as romance-related beef and not a RICO matter. 

“To your knowledge, this was particularly offensive to Mr. Combs because of Kid Cudi’s stature in the industry, right?” Estevao asked. “To my knowledge, yeah,” Cassie said. 

Prosecutors have argued that “Freak Offs,” drug-fueled encounters with male escorts that Diddy directed, were the point of his alleged racketeering scheme. Cassie’s cross came after two days of direct testimony where she described enduring Diddy’s abuse for a decade. On Wednesday, Cassie alleged that Diddy raped her in 2018 after they split up.