Diddy ‘Demanded $20,000’ From Cassie’s Mother to Bury ‘Freak Off’ Tapes

Regina Ventura and her family leave court after testifying in the Diddy trial on Tuesday, May 20, 2025. (Credit: YouTube/NBC News)

Sean “Diddy” Combs threatened to release explicit tapes of Cassie Ventura unless he received a $20,000 payment from her parents, the singer’s mother testified in the mogul’s sex trafficking trial.

Regina Ventura was one of several people to take the witness stand on Tuesday, May 20.

Ventura said when she learned her daughter was allegedly being abused by Combs she stepped in and tried to help. The mother-of-two told the court she took pictures of Cassie’s bruises when the singer returned home to New London, Connecticut for Christmas in 2011.

“I wanted to make sure we memorialized it,” Ventura testified, according to USA Today.

Related: Diddy Had Supplies for ‘Freak Offs’ at Time of Arrest, Federal Agent Testifies

When a prosecutor asked how Cassie sustained the injuries, her mother said, “She was beaten by Sean Combs.”

The jury was shown four photos that Ventura took of her daughter’s bruises.

($20,000 Demand)
Regina Ventura testified that her daughter had a volatile relationship with Combs, which she said Cassie hid from her family for years.  The mogul once took Cassie’s phone and police were called.

The prosecution asked Ventura about an email she received from her daughter in late 2011.

Ventura said Cassie contacted her saying Combs was threatening to release two explicit videos of her, including one on Christmas day, after he learned she was seeing rapper Kid Cudi, born Scott Mescudi.

“I did not understand a lot of it. The sex tapes threw me,” Regina Ventura testified, per the Associated Press.

She said Combs was upset that Cassie was spending time with another man and wanted to be repaid money he’d spent on his on-off girlfriend’s career.

“Sean Combs demanded $20,000. He said to recoup losses due to Mr. Mescudi, from my husband and myself,” Ventura testified.

The family took out a home equity loan and sent the money to Combs via wire transfer. To their surprise, the money was returned days later, she said.

The defense declined to cross-examine Ventura, letting her claims stand.

“I do not have any questions for you,” the mogul’s attorney Marc Agnifilo said.

Prosecutors said Kid Cudi will testify later this week.

(Personal Assistant Tells All)
Earlier in the day, Diddy’s former personal assistant David James testified. James said he worked for the Bad Boy Records founder from 2007 to 2009.

James told the court there were many unsavory parts of his job, like setting up hotel rooms for “freak off” sex parties.

He would book the rooms under an alias and bring clothes, razors, and toiletries for Combs, he said.

James told the court he was required to bring a medicine bag with drugs inside, including viagra, ecstasy, and pills made to look like former President Barack Obama. There would also be a bag with $10,000 cash inside, and he was tasked with supplying “personal items” like condoms, baby oil, and Astroglide.

James noted it wasn’t just Cassie staying in the rooms with Combs, there would be other women there as well.

(Suge Knight Tensions)
While the ex-assistant testified he never witnessed any physical violence between Combs and Ventura, he said he was troubled by escalating tensions between Diddy and Death Row Records founder Suge Knight, who’s now jailed in California for a separate manslaughter case.

One night in 2008, James and Diddy’s associate D-Roc were sent to Mel’s, an all-night diner in Los Angeles, to pick up cheeseburgers. They spotted Knight and his entourage there.

“D-Roc said, ‘That’s motherf–king Suge Knight. He went over and said, ‘What’s up?’ Suge didn’t recognize him. D-Roc said, ‘I’m Biggie’s boy,'” James testified.

James said they noticed Knight’s entourage had four black SUVs and weapons.

“I saw someone hand Suge Knight a gun. D-Roc said, ‘We gotta get out of here.’ We drove back to the house,” James recalled.

He said Diddy allegedly grabbed weapons and ordered them to return to Mel’s.

“Cassie was crying. Mr. Combs got in the vehicle. I saw three guns on his lap.” Cassie testified about the incident last week.

Once they got back to the diner, Knight was gone.

“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.”

He said he quit after the incident.

(Fiery Exchange)
Combs’ attorney Marc Agnifilo cross-examined James and attempted to grill him about the incident at Mel’s diner.

The former personal assistant held his own and told the attorney his questions were “crazy.”

“Didn’t you leave D-Roc at the diner?” Agnifilo asked. “That makes no sense,” James shot back, noting that he’d never leave someone at a diner at 4 a.m.

“I’m not asking what makes sense. I’m asking, Did you?” Agnifilo said. “No,” James responded.

The attorney then asked the ex-personal assistant if he’d cut a deal with prosecutors to avoid a co-conspirator charge.

James admitted he was given a proffer agreement. But he told Agnifilo if he wanted any more information he’d have to “ask my lawyer.”

(The Punisher)
Exotic dancer Sharay Hayes, known as “The Punisher,” also took the stand on day 7 of the trial.

“I was hired in 2012,” Hayes told the court.

The prosecutor asked why he was known as “The Punisher.”

“Playing basketball on West 4th Street,” he explained.

Back in 2012, he said a woman booked him for his first encounter with Cassie and Diddy. At the time, he had no clue who the clients were.

“She told me she and her husband wanted to create a sexual scene with baby oil,” he recalled.

Hayes said he was called to a hotel room in New York City for a “freak off.” He described the setting and said there were bottles of baby oil in bowls of water.

“I was expecting a crowd but there was no one else,” he said. He was handed $800 in cash.

“She told me not to acknowledge her husband, not to look at him when he came out,” Hayes said.

Later, after Combs watched him get intimate with Cassie, Hayes said he was handed another $1,200.

The prosecutor asked Hayes if he ever looked at Diddy. “Yes. He was naked, but I could not see his face,” he told he court.

He said Diddy was wearing a veil like mask. “Like what a Muslim woman wears, you see only the eyes. He had a bottle of Astroglide,” he said about Combs.

He said the couple booked him “8 or 12 times,” and the woman did not seem to be there by force.

Hayes finally realized his client was famous during an encounter at another hotel, where the message on the TV screen read: “Essex House would like to welcome Mr. Sean Combs.”

(Federal Agent Testifies)
Special Agent Gerard Gannon of Homeland Security Investigations (HSI) led the March 2024 raid on the Diddy’s Miami mansion.

Gannon told the court 80 to 90 law enforcement officers took part in the raid, because of the size of the sprawling property. An armored vehicle was also used to break through the gate around the home.

He said agents found parts from two AR-15-style weapons that had their serial numbers scratched off. Agents also found various sizes of high heels, sex toys, baby oil, personal lubricant and lingerie in the main bedroom closet.

Combs, 55, is charged with five felony counts, including racketeering conspiracy and sex trafficking. He pleaded not guilty to all charges. If convicted on all counts, he faces up to life in prison.


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About Anita Bennett

Anita Bennett is the editor and founder of Urban Hollywood 411. She can be reached on Twitter @tvanita.