Skip to main content

Hip-hop mogul Sean “P. Diddy” Combs is under a microscope after Homeland Security raided two of his properties — one in Los Angeles, and the other in Miami. Combs’ followers are looking back at his time with his ex-girlfriend, Casandra “Cassie” Ventura, who sued him for sexual assault and physical abuse. According to an insider, Ventura was “subdued” during Combs’ wild party days in Ibiza. Here’s what they said.

An insider said Casandra ‘Cassie’ Ventura was ‘subdued’ at Sean ‘P. Diddy’ Combs’ parties in Ibiza

Sean “P. Diddy” Combs was known for partying, and celebrities were invited to his lavish gatherings. An insider told The Sun that Combs had parties in Ibiza, a Spanish island in the Mediterranean Sea, that included “young girls,” drinks, DJs, and an overall sense of “hedonism” with “no expense” spared.

The insider noted that Combs was dating up-and-coming R&B artist Casandra “Cassie” Ventura at the time. Ventura and Combs began dating in 2007 and broke up for good in 2018. They have a 17-year age gap between them, which raises eyebrows now.

“When Cassie turned up with Diddy in 2010, at first, I thought she might be part of his entourage,” the insider noted. “She seemed really subdued and like she was there in body but not in spirit. I was shocked when one of his bodyguards told me she was Diddy’s partner. The age gap was apparent. She barely spoke and was subdued. It was as if she wanted to be seen but not heard. She spent most of the time holed up in their villa.”

The insider added that Ventura would stay home when Combs would leave the villa to party in Ibiza. “There were times I felt she looked unhappy,” the source continued.

Sean ‘P. Diddy’ Combs once explained how he was in love with Casandra ‘Cassie’ Ventura

A close-up of Cassie Ventura and Sean 'P. Diddy' Combs smiling with their heads next to each other
Cassie Ventura and Sean ‘P. Diddy’ Combs | Jewel Samad/AFP via Getty Images
Related

Expert Says Sean ‘P. Diddy’ Combs Made ‘Grandiose Gestures’ Like a ‘King’ on ‘Jimmy Kimmel Live!’

Casandra “Cassie” Ventura hit Sean “P. Diddy” Combs with a federal lawsuit for rape and abuse in November 2023, and they settled out of court the following day.

Before the abuse allegations, Combs discussed his love for Ventura while on The Wendy Williams Show. At the time, Combs had several kids with several different women. He explained that these were women he fell in love with at one point or another, but love generally didn’t work out for him.

“These are people who were my friends, and then I would get my heart broken, and then my friend would be there, and I would fall in love with my friend, and then I would get my heart broken again,” he explained.

However, when Wendy Williams asked Combs if he was in love, he said he was. Combs explained what he loved about Ventura.  “… It’s just, like, when a record comes on, the way she moves,” he explained. “When I look at her, the way she smiles. The way I see her look at me sometimes when I wake up, and she’s already awake.”

Her lawyer issued a statement after Homeland Security raided 2 homes

While Casandra “Cassie” Ventura settled with Sean “P. Diddy” Combs out of court, her followers think of her more in 2024 after Homeland Security raided two of Combs’ properties. Ventura’s lawyer issued a statement following the raid.

“We will always support law enforcement when it seeks to prosecute those that have violated the law,” the statement read, according to ABC. “Hopefully, this is the beginning of a process that will hold Mr. Combs responsible for his depraved conduct.”

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. 

For more on the entertainment world and exclusive interviews, subscribe to Showbiz Cheat Sheet’s YouTube channel.

Best in Entertainment