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Sean “Diddy” Combs’ defense team put Casandra “Cassie” Ventura in the hot seat Friday over her allegations that the rapper raped her, which she first revealed in her bombshell November 2023 lawsuit.
Combs’ attorney Anna Estevao pressed the “Me & U” singer, 38, during cross-examination over apparent discrepancies of when Ventura claimed Combs, 55, raped her back in 2018.
“At the April 2025 meeting, you told the government the alleged rape was in August of 2018, right?” the defense lawyer asked, to which the singer replied, “Yeah.” Ventura claimed in her lawsuit the rape occurred in September 2018.
Estevao then presented a series of texts from that time period in which Ventura continued to speak to Combs in a somewhat loving way despite them breaking up temporarily.
On Aug. 21, 2018, she sent him a text that read, “Hit me when you can [heart emoji],” per the trial, and admitted during her testimony that there “were still feelings” at that time.
On Aug. 25, 2018, Combs wrote to Ventura, “Can’t wait to see you. I miss you. Just need you to be positive and happy to see me” and she answered back in part, “All positive. Cant wait to see you too.”
Then on Sept. 12, 2018, the “Long Way 2 Go” singer seemingly appeared jealous when she questioned the “Bad Boy for Life” rapper over his yoga session with a woman she thought he was dating at the time. Combs denied dating that unnamed woman.
The defense then brought up yet another text exchange between Combs and Ventura on Sept. 26, 2018, in which the pair told each other that they “love” one another and when the “Last Night” rapper asked to “hold” the singer, she replied, “We can embrace lol.”
“You don’t say anything to the effect of the last time we saw each other you raped me?” Estevao asked in response to that particular conversation, to which Ventura confirmed, “Right.”
“In fact you’re saying you want to keep the peace?” the lawyer continued in the cross-examination, prompting Ventura to once again agree.
A text from Sept. 27, 2018, then showed Ventura and Combs had sex that night. At the time, she had already been dating her now-husband Alex Fine, with whom she is currently expecting her third child.
Ventura claimed on that stand that was not the evening she had been raped, and the defense brought up how Fine, 32, had once “punched a wall” when he learned his then-girlfriend had been raped.
On Oct. 5, 2018, Ventura texted Combs, “I know you don’t want to hurt me anymore. I miss you. I’m sad.”
She claimed on the stand that the next time they saw each other was at Kim Porter’s funeral that November.
When Combs claimed in a text on Nov. 19, 2018, that Ventura “left” him at the service, she responded, “I didn’t just leave you. I said goodbye a few times. I want to be with you but need to be with grandma.
“I know how crazy and painful this is. You compared me to Gina [Huynh] the other day and you posted Kim was your soulmate. What was the 11 years all about?”
The former couple never saw each other again after the funeral, per Ventura’s testimony.
The cross-examination concluded Friday afternoon and during the re-direct, Ventura made the revelation that Combs had allegedly beat her during one of their “Freak-Offs.” She broke down in tears at the time.
Ventura is not expected to be on the witness stand much longer, however.
The prosecution also argued in a letter filed late Thursday night that they fear Ventura’s lengthy testimony can cause the singer — who is eight months pregnant — to go into labor, which would “risk a mistrial.”
Ventura first took the stand Tuesday, when she was questioned by prosecutors over the infamous “Freak-Offs” with Combs — which lasted up to four days at times and caused her “painful” medical issues, his history of physical and emotional abuse of her and violence.
Since then, the “Love a Loser” singer has also had to testify about the shocking 2016 surveillance footage of their domestic dispute at a New York hotel and the raunchy texts they sent each other over the years.
Ventura also revealed during her bombshell testimony that Combs paid her $20 million in order to settle the aforementioned rape lawsuit. The rapper has said he did not admit guilt despite the settlement.
Combs has denied all of Ventura’s accusations and pleaded not guilty in his federal case.
The government has charged him with sex trafficking, racketeering and transportation to engage in prostitution. His federal trial is expected to last about two months.
If you or someone you know is affected by any of the issues raised in this story, call the National Domestic Violence Hotline at 1-800-799-SAFE (7233) or text START to 88788.
If you or someone you know is affected by any of the issues raised in this story, call the Sexual Assault Hotline at 1-800-330-0226.
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