Sean ‘Diddy’ Combs Accused of Threatening Cassie’s Family Over Relationship, Mother Testifies

NEW YORK – At the high-profile sex trafficking trial of hip-hop mogul Sean “Diddy” Combs, testimony from Casandra “Cassie” Ventura’s mother revealed a disturbing demand and threats tied to her daughter’s personal life.

Regina Ventura told a Manhattan federal court Tuesday that Combs angrily demanded $20,000 from her after learning Cassie was dating someone else — rapper Kid Cudi. The demand came with threats to release explicit sex tapes of Cassie and to harm both her and her new boyfriend.

“I felt physically sick when Cassie emailed me about the threats,” Regina said. “I didn’t understand it all, but the mention of sex tapes shocked me.”

Fearing for her daughter’s safety, Regina said she took out a home equity loan to pay Combs the demanded money. “He was angry because he had spent money on her, and she went with another person,” she explained. The money was later returned, and Cassie resumed her relationship with Combs.

Photos shown to the jury revealed bruises on Cassie, allegedly from when she visited her mother at Christmas 2011.

Weapons and Wild Parties: FBI Raid Uncovers More Details

Jurors were shown parts of two AR-15 rifles seized during a 2024 raid on Combs’ Miami mansion on Star Island. Homeland Security Agent Gerard Gannon described the dramatic operation — armored vehicles breaking through security gates and teams arriving by boat.

Besides weapons, agents found items prosecutors linked to Combs’ so-called “freak-off” sex parties: lingerie, sex toys, baby oil, lubricant, and condoms.

The trial, expected to last two months, is shining a light on the darker side of the music mogul’s private life. Combs, 55, has pleaded not guilty. Conviction could mean 15 years to life in prison.

Former Assistant’s Shocking Revelations

David James, Combs’ personal assistant from 2007 to 2009, painted a picture of a dangerous, chaotic environment. He recalled being forced to drive with Combs holding three handguns in the backseat — a moment that made James quit the job.

James described his duties, which included stocking hotel rooms with Combs’ personal requests: fresh underwear, vodka, baby oil, Viagra, and condoms.

One startling incident: James opened a hotel room door in 2008 to find Cassie in bed with a naked stranger fleeing the scene.

He also testified that Combs recorded videos of him dancing wildly and threatened to keep the footage as leverage to keep him in line. James said he was subjected to lie detector tests when Combs tried to track down stolen cash and a watch.

James revealed Combs’ heavy drug use — Percocet by day, ecstasy by night — with drugs delivered by security staff, including a pill disguised as former President Obama.

More on the ‘Freak-Off’ Parties

Exotic dancer Sharay Hayes, known as “The Punisher,” described his introduction to Combs and Cassie’s wild “freak-offs.”

Hayes said he was hired under the pretense of performing a striptease for a birthday party but found himself part of a more intimate gathering involving Combs disguised behind a cloth mask.

He recalled bottles of baby oil in water bowls and being handed large sums of cash — $800 upfront, then another $1,200 after witnessing a sexual encounter between him and Cassie.

“I was a fan of Combs but didn’t realize it was him until later,” Hayes said, recalling a hotel TV welcoming “Mr. Sean Combs.”

What’s Next?

More witnesses, including Kid Cudi (Scott Mescudi), are expected to testify in the coming days, as the trial continues to unravel the complex and troubling allegations against Sean Combs.