Cassie’s mother says Sean ‘Diddy’ Combs demanded US$20K because her daughter was seeing someone else

Sean ‘Diddy’ Combs’ former assistant tells the jurors what it’s like to work for the music mogul, and singer Dawn Richard said she witnessed Combs punch Ventura

NEW YORK — Warning: Graphic content

An angry Sean “Diddy” Combs demanded US$20,000 from Casandra “Cassie” Ventura’s mother and threatened to release explicit sex tapes of his longtime girlfriend after learning she was dating someone else, the mother testified Tuesday at the hip-hop mogul’s sex trafficking trial.

Regina Ventura said she felt “physically sick” when her daughter sent her an email in late 2011 to say Combs threatened to release two explicit videos of her and send someone to hurt her and the man she was seeing, the rapper Kid Cudi.

“I did not understand a lot of it. The sex tapes threw me,” Ventura told the Manhattan federal court.

Ventura, of New London, Connecticut, said she then received a demand from Combs for $20,000.

“He was angry that he had spent money on her and she went with another person,” she said.

Cudi, whose real name is Scott Mescudi, is expected to testify Wednesday or Thursday.

Ventura said she and her husband used a home equity loan to pay Combs, telling jurors “I was scared for my daughter’s safety.” Days later, she said, the money was returned, and before long, Cassie was dating Combs again.

Ventura testified for less than a half-hour, in part because defense attorney Marc Agnifilo declined to cross-examine her. During her testimony, the jury was shown photos of bruises on Cassie’s body that Ventura testified were taken when her daughter came home for Christmas in 2011.

Before the jury arrived Tuesday, Agnifilo tried to persuade Judge Arun Subramanian to disallow the testimony, saying it was “purely prejudicial” because it illustrated the wide difference between the financial status of the Ventura family and Combs. The judge allowed it though, saying the threats to release sex tapes and harm Cassie made it an instance of “potential extortion.”

A federal agent describes a raid of Combs’ home

Jurors also saw parts of two AR-15 rifles found last year during a raid on Combs’ mansion on Star Island, a celebrity enclave off of Miami.

Homeland Security Agent Gerard Gannon testified that investigators in March 2024 rammed through Combs’ security gate in an armored vehicle and had teams on boats nearby. Besides weapons, they found 7-inch high heels and items prosecutors say Combs used at his freak-off sex marathons like lingerie, sex toys, baby oil, lubricant and condoms.

The testimony came in week two of a projected two-month trial. Combs, 55, has pleaded not guilty. If convicted, the Bad Boy Records founder could face 15 years to life in prison.

A former assistant describes working for Combs

Earlier Tuesday, David James, Combs’ personal assistant from 2007 to 2009, told the court that the job seemed to come with increasing perils. He said he quit when he realized Combs had put his life in danger by forcing him to drive a car as the angry rapper sat in the back with three handguns on his lap.

James said his job sometimes required him to ensure that hotel rooms where Combs stayed under the name “Frank Black” were stocked with the musician’s comforts, including fresh underwear, an iPod, apple sauce, vodka, baby oil, Viagra and condoms.

There were also surprising moments, James said, like one in 2008 when Combs asked him to bring an iPod from his Miami home to a hotel room. Upon entering, James said he saw Cassie on the bed with a white comforter pulled up to her neck and an unfamiliar naked man running from the room.

Another time, he said Combs summoned him to his office to show him video he’d recorded at a party of James dancing wildly and told him: “Ok. I’m going to keep this footage in case I ever need it.” James said he took it as a threat to keep him in line.

Cassie testified last week that Combs threatened that if she didn’t do as he said, he would release videos of her having sex with male sex workers during freak-offs.

James also described being required to take lie detector tests twice when Combs was trying to find out who stole cash and a watch.

He said Combs was on drugs nearly every day, often taking Percocet by day and ecstasy by night. When he stocked Combs’ hotel rooms, he said, drugs were in a bag dropped off by security, including a pill meant to look like former President Barack Obama.

The moment when James saw the three guns on Combs’ lap came when he testified that he was involved in Combs’ attempt to confront his music industry rival Suge Knight at a Los Angeles diner in November 2008 -- an incident that Cassie also testified about. He said he quit soon afterward.

“I was real shook up by it,” James testified. “This was the first time being Mr. Combs’ assistant that I realized my life was in danger.”

More testimony about freak-offs

Before Tuesday’s lunch break, Sharay Hayes, an exotic dancer known as “The Punisher,” testified that Combs and Cassie brought him into the freak-offs world. He said a woman -- Cassie using a pseudonym -- called and told him it was her birthday and that her husband said she should hire a dancer.

Hayes said he arrived at a Manhattan hotel room expecting to perform a striptease for a small group of people but instead found the woman who hired him -- whom he later found out was Cassie -- alone with an otherwise naked man who hid his face with a burqa-like cloth. That man, he said, turned out to be Combs.

Hayes recalled seeing bottles of baby oil in bowls of water and getting handed a stack of $800 in cash. Later, after Combs watched him have a sexual encounter with Cassie, he said he was handed an additional $1,200. He said he was a fan of Combs but didn’t realize it was him in the room until a subsequent encounter at another hotel where the message on the TV screen said: “Essex House would like to welcome Mr. Sean Combs.”

This story was updated to correct that Regina Ventura said Combs demanded $20,000 from her, not $10,000.

Resources for sexual assault survivors in Canada

If you or someone you know is struggling with sexual assault or trauma, the following resources are available to support people in crisis:

• Call 911 if you are in immediate danger or fear for your safety.
• The Canadian Association of Sexual Assault Centres' website has a comprehensive list of sexual assault centres in Canada that offer information, advocacy and counselling. 
• The Ending Violence Association of Canada‘s website has links to helplines, support services and locations across Canada that offer sexual assault kits.
• Indian Residential School Survivors Society crisis lines: [phone] or [phone] (24/7)
• Toronto Rape Crisis Centre crisis line: [phone] (24/7)
• Canadian Human Trafficking Hotline: [phone] (24/7)
• Trans Lifeline: [phone]
• Suicide Crisis Helpline: call or text 988 (24/7)
• Sexual Misconduct Support and Resource Centre for current and former Canadian Armed Forces members: [phone]
• Read about your rights as a victim on the Canadian Resource Centre for Victims of Crime website.