Diddy’s ex-assistant tells jury he set up hotel rooms for ‘Freak Offs’

Editor’s Note: This story contains discussions of rape or sexual assault that may be disturbing. Reader discretion is advised. If you or someone you know has been sexually assaulted, you can find help and discreet resources on the National Sexual Assault Hotline website or by calling 1-800-656-4673.

(NewsNation) —The federal trial against Sean “Diddy” Combs resumes Tuesday with his former personal assistant, David Jones, returning to the stand. 

Prosecutors continued their questioning of Jones, who worked for Combs from 2007 to 2009. 

Jones gave emotional testimony Monday, saying one of Combs’ staff members pointed to a photo of Combs on the wall and told him, “This is Mr. Combs’ kingdom. We’re all here to serve him.”

Ex-Diddy assistant testifies rapper said Cassie was ‘moldable’ and ‘young’

Combs had described Casandra “Cassie” Ventura as “moldable” and also said “she’s good. I got her right where I want her. She’s young,” to James, he testified.

He also said he told Ventura to leave Combs after seeing his treatment of her, and she told him, “I can’t. I can’t get out. You know, Mr. Combs oversees so much of my life.”

James testified that he never witnessed Combs physically assaulting Ventura, however he did observe the two have numerous arguments over the direction of the singer’s career.

Part of his role as Combs’ assistant was to set up hotel rooms ahead of time for his boss, which was referred to as “advancing” rooms.

Ex-Diddy assistant set up hotel rooms with baby oil, Viagra, and drugs

James brought Combs’ Louis Vuitton bag which contained roughly $10K in cash and a medicine bag that held 25-30 pill bottles carrying Viagra, Tylenol, and Percocet. Combs also took Ecstasy pills with President Obama’s face on them.

The former Combs assistant also purchased lubricant for the fallen music mogul, but with cash as he was told the musician did not want those items tracked back to his record company.

James recalled an incident in Miami in 2008, when he entered a hotel room when Ventura was asleep with an unidentified naked man wearing a condom and Combs was in the shower. The man left when James came into the room.

  • Courtroom sketch of Sean "Diddy" Combs
  • A courtroom sketch of Sean "Diddy" Combs
  • A courtroom rendering of Sean "Diddy" Combs, right, looking at jurors as they file into the jury box

Diddy would conduct business under the influence of drugs, ex-assistant says

The former assistant testified that Combs would do drugs daily and conduct business under the influence. When asked if Combs did drugs in the studio, James replied, “Of course.”

James said he bought drugs for Combs or his friends twice, and he himself only took drugs once one New Year’s Eve.

He said that Combs called him in and asked if he was dancing around. According to James, Combs had a videographer present at his parties.

Combs allegedly told James, “Ok. I’m going to keep this footage in case I ever need it.”

The ex-assistant said the release of that footage would be embarrassing for him.

James testified that Combs made him take lie detector tests on two occasions when the record label executive was trying to find out who stole money and a watch.

Ex-Diddy assistant recalls armed Suge Knight encounter

In November 2008, James said on the stand that he was involved in the incident Ventura recalled during her testimony that Combs took guns to confront Suge Knight.

James testified that he was in the vehicle with a Combs’ bodyguard at 4 AM to pick up food from Mel’s Drive-In when the security guard allegedly spotted someone handing a gun to Knight.

James said he and the bodyguard returned to Combs’ house roughly 10 minutes away from the restaurant.

Combs wanted to go to the diner, and Ventura was yelling at him not to go, James testified.

James said Combs told him to drive him and the security guard, D-Roc, to the diner. While driving James said he saw the rapper have three guns on his lap in the car.

When they got to the diner, Knight and his group, had already left, James recalled.

Combs, the security guard, and James returned to the Los Angeles residence.

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

Cassie’s mother testifies Diddy demanded $20K to stop release of sex tapes

Ventura’s mother, Regina Ventura, testified on Tuesday that the rapper threatened to release sex tapes of her daughter after learning the singer was dating Kid Cudi.

In 2011, Ventura received an email from her daughter claiming that Combs was going to publish sexual material of her, and threatened to hurt the singer, and Kid Cudi. She felt “physically sick” after learning this information.

In her less than thirty minutes on the stand, Ventura said, “I did not understand a lot of it. The sex tapes threw me.”

Ventura testified that Combs demanded $20,000 in order “to recoup money he had spent on her because he was unhappy she was in a relationship with Kid Cudi.” She added that the music label executive “was angry that he had spent money on her and she went with another person.”

In order to come up with the hefty sum, Ventura took out a home equity loan because she was, “scared for my daughter’s safety.”

The money was returned shortly after, and Combs and Cassie reconciled.

Photos were shown of her daughter’s thigh, lower back, and shoulder bruised. Ventura said, “She was beaten by Sean Combs.” She testified that images were taken in December 2011, and it was when her daughter told her she was abused by the hip-hop mogul.

Male exotic dancer testifies he was hired to create a “sexy scene” with baby oil

Sharay Hayes, who worked as a male exotic dancer under the name “The Punisher,” said on the stand on Tuesday that he was hired in Fall 2012 by Ventura and Combs.

He said a woman called him under the guise of a birthday party, but when Hayes arrived there was no party.

Hayes said that he did not recognize Ventura at first. She was wearing a wig and a bathrobe. She informed him that he was there to create a “sexy scene” with baby oil.

The stripped was told the woman’s husband would be entering the room and to not acknowledge him.

A naked Combs entered with a face covering and holding lubricant. The former music label executive did not engage with Hayes. Combs sat behind a table and masturbated and gave Ventura “subtle directions.”

After about 25-45 minutes, Combs exited, and Ventura followed him.

Ventura returned and asked if he wanted to “finish.” Hayes rejected the offer.

Cassie’s former friend testifies about alleged abuse

James follows the testimony of Ventura’s former friend Kerry Morgan, who corroborated that Combs engaged in violence with the singer. 

Morgan said she saw the rapper assault Ventura twice, pulling her hair, kicking her and pushing her.

Witness Kerry Morgan arrives at Federal Court for the Sean “Diddy” Combs trial, on Monday, May 19, 2025, in New York. (AP Photo/Ted Shaffrey)

She also said Ventura was at the fate of Combs and that once she heard the record label executive say he “owned” his then-girlfriend and signed artist.

Morgan said she was also at the receiving end of his violence in 2018 when Combs choked and then smashed a wooden hanger on her head when she came to Ventura’s Los Angeles home enraged because he thought Ventura was dating someone else.

The attack left her with a concussion, Morgan told jurors. 

Morgan told jurors she was going to sue Combs but that Ventura made her sign a nondisclosure agreement in return for $30,000 to keep quiet while also accusing her of “milking” and “overexaggerating” the attack. 

The episode ended their long-term friendship, and the two haven’t spoken since, she said. 

Combs is facing federal charges of racketeering conspiracy, sex trafficking by force, fraud or coercion and transportation to engage in prostitution.

The Associated Press contributed to this report. 

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