Cassie Drops Bombshell: Diddy Was Dating Her and Kim Porter Around the Same Time
Casandra “Cassie” Ventura stepped into the courtroom for hip-hop mogul Sean “Diddy” Combs’ trial as a witness determined to be heard. On the opening day of testimony, the singer and former partner of Combs offered a searing account of alleged abuse, control, and exploitation. Her testimony marked a powerful turning point in the case, transforming years of whispered allegations into a detailed, public reckoning. On May 13, 2025, Ventura dropped a bombshell: Combs dated her and Kim Porter around the same time. Here’s what we know.
Casandra ‘Cassie’ Ventura says Sean ‘Diddy’ Combs dated her around the same time as Kim Porter
Casandra “Cassie” Ventura, the singer and former partner of Sean “Diddy” Combs, has provided detailed testimony in the ongoing federal sex trafficking trial. Ventura testified that Combs coerced her into participating in orchestrated sexual encounters with male sex workers, referred to as “freak-offs.” These sessions, which she claimed occurred nearly weekly from 2008 to 2017/18 in cities such as Los Angeles, New York, and Ibiza, involved drug use and were filmed for potential blackmail.
Ventura’s testimony also gave the jury a clear picture of her relationship timeline with Combs. She signed on to Combs’ label in 2006 at 19 years old.
“We started to spend more time together,” Ventura recalled around her 21st birthday, according to NBC News. “We were spending a lot of time together one-on-one — it was not public for many years. He just didn’t want it to look bad but also knew it was because of his children and personal things like his family.” Ventura then clarified that Combs publicly dated Kim Porter around this time.
Porter and Combs dated from the mid-’90s to 2007. They had three kids together: Christian “King” Combs and twins D’Lila Combs and Jessie Combs.
Kim Porter confronted Sean ‘Diddy’ Combs about his cheating behavior
Kim Porter and Sean “Diddy” Combs had an honest interview with Essence. Within the interview, they opened up about Combs’ high-profile relationship with Jennifer Lopez from 1999 to 2001 — a time when he was still in love with Porter. Combs admitted that he didn’t necessarily believe in monogamy.
“Do you really think that God meant for a man to have just one wife?” he said in the interview. “Or a woman to have one husband? Do you think God meant it that way?”
“Do you really want me having sex with some other man?” Porter responded. “You want that to happen?”
“No,” he replied, “but God made us different.”
“That’s such a cop-out,” Porter scolded. “I could be just like you. I choose not to be.”
“Sometimes things happen,” Combs added. “This is the most monogamous I’ve ever been in my life … that’s all I’m trying to say.”
The mogul’s former head of security said he spoke to both Casandra ‘Cassie’ Ventura and Kim Porter
Sean “Diddy” Combs’ former head of security, Roger Bonds, spoke on Piers Morgan Uncensored in 2024 about how he had conversations with both Kim Porter and Casandra “Cassie” Ventura. Porter knew about Combs’ infidelity and spoke to Bonds about it.
“Me and Cassie had conversations. Me and Kim had conversations,” Bonds said. “Kim was basically telling me, she said, Bonds, I got four of them. She said, I allow these things to happen as far as him messing around with girls and stuff like that. She said, when I get tired of it, he’s gonna know.”
As for Ventura, Bonds noted she appeared more naive. “And Cassie, you got to a point where it’s like you’re talking to your daughter,” he continued. “I’m giving her advice, but Cassie was so scared that the advice that you would give her, she would go back and tell him. And that would make you not want to talk to her, or give her advice, or tell her what she should do, because she would go back and tell him, and they were alone.”
How to get help: In the U.S., call the RAINN National Sexual Assault Telephone Hotline at 1-800-656-4673 to connect with a trained staff member from a sexual assault service provider in your area.
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