Cassie Was Diddy’s DeFacto Slave … Made Her Shave Her Head ‘Whatever He Wants’

Sean “Diddy” Combs‘ relationship with Cassie Ventura spanned 11 years. Their on-again, off-again union was fraught with challenges, as Ventura reportedly had to adhere to Combs’ demands. However, the entertainment mogul went one step too far when he asked Ventura to shave her head. Her response? “Whatever Sean wants.”

Sean Combs’ disturbing request of Cassie Ventura revealed by Yung Joc

In a 2022 interview with Vlad TV, rapper Yung Joc shared a disturbing exchange between Sean “Diddy” Combs and Cassie Ventura. Furthermore, he couldn’t believe what Combs’ asked his longtime girlfriend to do.

“I took my wife to Miami, my ex-wife, for her birthday. We were on a yacht, drinking Ciroc,” Joc began.

“I hit up Puff, I said ‘I’m in Miami, on a yacht. I’m gonna come pass your house,'” he continued. Combs responded, “He said ‘Pull up, me and Cassie are just chillin.'”

Later the men went jet skiing and spent the afternoon riding jeeps. That night, the two couples went to a club. After seeing a woman with the side of her head shaved, Combs had an idea.

“Puff jumped up and said, ‘Yo Cassie. Tomorrow, I want you to shave the side of your head,'” Joc recalled.

“I said, ‘What the f*** kind of request is that?’ So I looked at Cassie and I asked, ‘You not about to do that are you?'”

Thus Ventura answered, “Whatever Sean wants I’m gonna do.” Joc asked Ventura to send him a picture if she did it. She subsequently fulfilled Combs’ request.

But Ventura later told VIBE that the decision to shave her head was her own. “I had long, big curly hair for so many years and I just wanted to try something different. I actually didn’t have the intentions of shaving so much hair but when I went there I wanted to go all the way and kind of land in punk.”

Cassie Ventura and Sean ‘Diddy’ Combs’ relationship came to an end in 2018

In October 2018, Cassie Ventura’s representative confirmed to the LoveBScott.com website that she and Combs had split for good. The statement read, “They are indeed no longer together and haven’t been for months.”

Ventura filed a lawsuit against Combs in November 2023, accusing him of sexual assault and physical abuse. The lawsuit states, “Cassie—Ms. Casandra Ventura—was held down by Mr. Combs and endured over a decade of his violent behavior and disturbed demands. For Ms. Ventura, the ‘dark times’ were those she spent trapped by Mr. Combs in a cycle of abuse, violence, and sex trafficking.”

It went on to detail that Combs allegedly raped Ventura in her own home after she tried to leave him, She subsequently alleged she was often punched, beaten, kicked, and stomped on; resulting in bruises, burst lips, black eyes, and bleeding.

The lawsuit was settled a day later. However, the terms of the settlement were never publicly revealed.

Sean Combs was arrested and jailed in September 2024

Sean ‘Diddy Combs’ | Bryan Bedder/CP/Getty Images for CP

In May 2024, CNN released a video of Sean “Diddy” Combs savagely beating Cassie Ventura in a hotel room hallway. The incident occurred at the now-closed InterContinental Hotel in Century City, Los Angeles in 2016.

Following, Combs responded to his actions on Instagram. He said, “My behavior on that video is inexcusable. I take full responsibility for my actions in that video. I was disgusted then when I did it. I’m disgusted now,” he added.

“I went and I sought out professional help, I got into going to therapy, going to rehab. I had to ask God for his mercy and grace. I’m so sorry. But I’m committed to being a better man each and every day. I’m not asking for forgiveness. I’m truly sorry.”

Combs was arrested on Sept. 16, 2024. One day later, an indictment against the entertainer was unsealed. He was charged with sex trafficking, racketeering conspiracy, and interstate transportation for prostitution.

Page Six reported the indictment included detailed descriptions of drug-fueled sex parties and other illegal activities allegedly hosted by Combs on his property. The mogul called these sessions “Freak Offs.”

Combs is currently held at a Federal correctional facility and housed in a special protection section. He stood before judge Judge Arun Subramanian during a status hearing on Oct. 10. A trial date is set for May 5, 2025. 

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.