Regina Ventura: I felt physically sick
What the defense wanted no one to hear. Diddy extorted $20,000 from Cassie Ventura's family.
It is the second week of the federal prosecution against Sean Diddy Combs. While it may be a new week, the theme is the same. Sex. Abuse. Control.
Several made their way on and off of the witness stand today. Beginning with final testimony from David James, the once personal assistant of Diddy. Today we also heard from Regina Ventura, Cassie’s mother, another homeland security special agent, and the escort/ male dancer dubbed “The Punisher”.
*Warning: Graphic material
Assault by Assistant
David James finished his testimony Tuesday morning. Recounting a time that Sean Combs was upset with him. He had assaulted a female chef working for Combs. Defense attorney Marc Agnfilo first asked James if he had ever choked the chef. This prompted a sidebar and then questioning continued. David James recalled when the chef was trying to tell him how to do his job, he grabbed her wrists, and told her to “stay in her fucking lane”.
To this- Diddy told him “you can’t be hitting women” and directed him to write her a note and get her a gift. The gift? A blunt. David James rolled the chef a blunt, and all was well.
James also testified further on what it was like to work for Sean Combs and told the jury about a time he worked for 21 days straight.
James said that Combs’s security detail used to have a saying: “Do you know what rhymes with tired?” (The answer: Fired.)
The questioning ended with a story including former Diddy security, a man named Roger Bonds. He and Bonds met two women at a hotel, had drinks, and then brought them back to Combs’ home. What James didn’t know was that the women were apparently escorts. After they had relations, Bonds instructed James to pay the woman $200. However the night ended with the woman wanting a shower- which James charged her $200 for. Agnfilo seemed to get a kick out of this. He laughed. “So you got your money back?”.
Regina Ventura
Mrs. Ventura took the stand and recounted the horror when she first found out her daughter was being abused by Sean Combs. This was shared with her in an email written by Cassie under a fake name as she traveled home to Connecticut for Christmas. When Cassie arrived, her mom photographed the many bruises on her body. These exhibits have now been released publicly.
I was scared for my daughter’s safety.



Ms. Ventura explained to the jury that these were the result of Sean Combs finding out about Cassie’s relationship with Kid Cudi, real name Scott Mescudi. Combs felt it was an insult for Cassie to date someone else in hip-hop.
She believed that he was going to harm her daughter.
To add insult to Cassie’s many injuries, Diddy demanded $20,000 for money he had spent on Cassie Ventura. Threatening to release ‘freak off’ videos if he was not paid. Regina Ventura and her husband took out a $20,000 loan against the equity in their home and wired the funds to Sean Combs. In roughly four or five days- it was returned.
Regina Ventura said she received an email about the sex tape release threat and felt “physically sick.”
Marc Agnfilo for the defense declined to question Regina Ventura.
Sharay Hayes “The Punisher”
The government called yet another male escort involved in ‘freak offs’. A tall man, well put together, and muscular walked down the aisle and took the stand. After viewing an exhibit, a photo of Combs and Cassie, Hayes confirmed he knew them.
His first encounter with them was in New York when he was hired to give a woman a “sexy erotic scene” in the Fall of 2012. Painting a similar picture as the first male escort witness- he was led to believe it was a birthday gift for the woman from her husband. Initially, he did not recognize Cassie. He was told specifically not to acknowledge the husband or say anything to him. Hayes and Cassie began rubbing baby oil on each other and after a while a man came into the room. Nude. Holding astroglide. Half of his face covered. Directing Hayes and Cassie as he pleasured himself.
a man he now understands was Combs, who sat a table, naked except for a veil “like a Muslim woman would wear.” Hayes said he was instructed to have no communication with the man.
Hayes was given $800 upon arrival and an additional $1,200 when he was leaving. He was then asked if he wanted to “finish” but replied that he wanted to keep things professional.
He would meet them again. 8 to 10 times. Eventually, he would realize this couple was Sean Combs and Cassie Ventura. When he turned on a TV in a hotel room while waiting for a ‘session’ to start, a welcome screen appeared reading, “The Essex House would like to welcome Mr. Sean Combs.”
“Ironically,” Hayes testified, “I was a fan.” He said he later looked at Combs’s Instagram account and recognized Ventura in the photos.
Hayes also testified that typically a ‘freak off’ would start between 2 a.m and 3 a.m- they could last for hours or days. Describing them as “fairly predictable”. Dim lighting. Sheets on furniture. Starting with rubbing baby oil on one another. Recalling one time when Sean Combs threw condoms on the couch and said he was “ready to see them fuck”. Another when Sean Combs dropped a stack of money on the bed as Hayes and Cassie had sex. A nod of approval.
Ventura seemed to seek “cues” from Combs and sometimes winced or sighed in response to the instructions
Xavier Donaldson, for the defense, cross-examined Sharay Hayes. Asking about when he began his career in exotic dancing, and what he typically did at various events when called to work. It would appear Donaldson does not know what “dry humping” is, and Hayes had to repeat it several times.
“There were no cues about any discomfort, correct?” defense lawyer Xavier Donaldson asked. “That’s based on your 25 years experience doing dry humping on hundreds of thousands of women?”
“Correct,” Hayes said.
Donaldson has now become somewhat known for the way he questions. Really making a statement, but turning it into a question at the end with “correct?”. The answer to questioning regarding cues about discomfort may contradict Hayes’ earlier testimony when he stated Cassie sometimes “sighed” or “whimpered” at cues given by Sean Combs.
The state then questioned Hayes on whether Cassie enjoyed herself and how would he know if she did or not.
“What made you think Ms. Ventura was enjoying herself?” Foster asked. Hayes described performing oral sex on Ventura, after which he said she scooted toward him as if to get ready for intercourse.
Gerard Gannon, a special agent with Homeland Security
Thankfully the day ended with lighter testimony from an agent with Homeland Security. Gannon was tasked with planning the raid on Sean Combs’ home on Star Island in Miami. Much of the questioning surrounded the logistics, when the raid was done, and so on.
The government seems to be getting a head of defense with a line of questioning regarding the use of a tank and ramming the security gate. Defense has previously said this was “excessive”. Agent Gannon testified it was normal to enter as quickly as possible. Normal to ram a gate. The time the raid was performed was unusual, but it was because of information that Combs and his family were going out of the country- so they waited until they had left the property. The number of agents used was also unusual, but it was because of the size of the home. Roughly 20,000 sqft.
Gannon said using a tank was not unusual, nor was breaking the gate. He described it as “standard practice” in the interest of gaining quick access to the property.
The prosecution then asks about items found during the raid on the Star Island mansion.
He testified that in the main bedroom’s closets, federal agents found parts of AR-15 rifles and corresponding accessories, such as red-dot optic plates, which help the shooter be more accurate. Photos from the same bedroom showed a column of shelves with AR-15 components as well as platform high heels, sex toys, baby oil, lubricant and lingerie, according to Gannon’s testimony.
Gun parts with serial numbers that had been defaced were recovered from Sean Combs’s bedroom at his Star Island mansion last year, Homeland Security agent Gerard Gannon testified. He said that defacement typically occurs when the gun holder wants to prevent law enforcement from tracing the weapon.
The government then drew Agent Gannon’s attention to a pair of platform heels recovered during the raid.
With that… court ended for the day. Testimony will resume tomorrow with Agent Gannon’s questioning by prosecution.
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