Diddy trial recap: Cassie's mom said she wired Diddy $20K, was sick over alleged threats
This page reflects the news from Sean "Diddy" Combs' trial on Tuesday, May 20. For the latest updates from Diddy's trial, read Paste BN's live coverage for Tuesday, May 21.
This story contains graphic descriptions that some readers may find disturbing.
A stream of witnesses in Sean "Diddy" Combs' federal sex-crimes trial gave emotional testimony on the one-time mogul's alleged physical, sexual and emotional abuse as prosecutors lay out their case.
Regina Ventura, the mother of Combs' ex-girlfriend Cassie Ventura Fine, told the court on May 20 she was "physically sick" over the rapper's alleged abuse and said she was once pressured to send him $20,000 after he raged at her daughter. "I was scared for my daughter’s safety," Ventura told jurors.
David James, who worked for Combs from 2007 to 2009, also took the stand on May 20, telling the court he feared for his life in one intense incident. James came face-to-face with Suge Knight at a Los Angeles restaurant, and when Combs found out, he and a group of men allegedly tried to find Diddy's longtime music rival while armed with multiple guns.
Scott Mescudi, better known as rapper Kid Cudi, is also expected to take the stand this week. Combs allegedly threatened the musician after he and Ventura Fine dated briefly over a decade ago.
Combs, 55, was arrested in September 2024 on charges of sex trafficking, racketeering and transportation to engage in prostitution. He has pleaded not guilty to all charges.
Special agent describes raiding Diddy's home
Homeland Security Special Agent Gerard Gannon, the final witness of the day, told the court that on March 24, 2024, he was part of a team that searched of Combs' Miami mansion.
Nearly 90 agents were involved in the search, which happened while Combs and his family were not in the home. Gannon said law enforcement found the upper receivers of AR-15 weapons, as well as gun magazines.
Agents also found sex toys, lubricant and baby oil in the home, all parts of the alleged drug-fueled freak offs Combs conducted for years.
Former exotic dancer Sharay Hayes recalls highly choreographed sexual performances
Sharay Hayes, a 51-year-old former exotic dancer who went by the nickname "The Punisher," took the stand after Cassie's mother.
Hayes said he was hired to have sex with Ventura Fine in New York every few months, sometimes for multiple days at a time. Combs would often give directions, he said, and Ventura Fine was once visibly startled after Combs dropped a stack of money onto the bed during an encounter.
After the two allegedly had sex, Combs would then go to another room, and Ventura Fine would follow, Hayes said. When she returned in a bathrobe, Hayes said it “gave me a clear indication that we were done."
Combs would direct them to have oral or penetrative sex, mostly interacting with Ventura Fine, Hayes told jurors. Asked whether he thought she was enjoying herself, Hayes said he wasn't sure, but he did note that Cassie would often wince or sigh at Combs' directions. There “appeared to be frustration with the frequency of directions,” he explained.
He said he “did not” ever hear Ventura Fine say no to a direction from Combs, and that while he did not use illegal drugs or alcohol, he was offered the substances. He said neither Combs nor Ventura Fine appeared to be intoxicated.
“It created some discomfort that could affect me and my performance,” Hayes said about Combs’ directions, saying he took Cialis, Viagra or similar medication. “It was a lot of pressure,” Hayes said about getting and maintaining an erection.
Former dancer Sharay Hayes describes hotel room covered in sheets, baby oil bottles
Hayes said he was first hired in 2012 by Ventura Fine, who told the dancer at the time it was her birthday, using the alias "Janet." Hayes said he was told over the phone he would be performing a "strip tease for a small group of friends" at Trump Tower in New York.
Ventura Fine greeted him at the hotel room door in a bathrobe and a wig, Hayes said, and invited him inside. "She explained to me that she didn’t want me to actually dance," Hayes said, revealing that instead, she wanted him to "create a sexy, exotic scene," in which they would apply baby oil to each other and "her husband would eventually come out to watch."
Ventura Fine then handed him $800 in cash and told him not to acknowledge or look at her husband, adding that all furniture in the room was covered in sheets, and there were several bottles of baby oil around. "She started pouring it on herself, and I did similar," he said, adding that out of the corner of his eye, he saw a naked man come into the room wearing a cover on his face that only showed his eyes.
The interaction lasted about 25-35 minutes, he said, before Cassie allegedly handed him an additional $1,200 in cash.
He said he was called about a dozen times to create similar scenes. Hayes explained that he didn’t realize the man was Combs until one instance at the Essex House Hotel, also located in New York. While Hayes was waiting for the scene to start, he turned on the TV, and there was a welcome screen that said, "The Essex House would like to welcome Mr. Sean Combs."
Diddy’s lawyer to Cassie’s mom: 'I don't have any questions'
Combs' defense team chose not to question Cassie's mother in court.
During cross-examination, Combs' lead lawyer Marc Agnifilo said, "Good afternoon, Ms. Ventura." "Good afternoon," Ventura replied. Then, Agnifilo told the star witness's mom that "I don't have any questions for you, thank you."
Cassie's mom tells court she tried to 'hit' Diddy after he took daughter's phone
In August 2016, Ventura went to Los Angeles for Cassie's birthday. "Cassie, Casandra, was out with Sean and he stole her phone," Ventura alleged in court. During the visit, Ventura testified that she got into a physical fight with the embattled music producer.
"We had a bitter argument outside her apartment," Ventura said. She testified that a Combs security guard D-Roc, whose legal name is Damion Butler, was also there between them. Ventura recalled that "we were arguing about the phone. I wanted the phone back. I was yelling, screaming and trying to hit him."
After returning Cassie's phone, Ventura said Combs took her daughter's vehicle.
Cassie's mom explains she took pictures of daughter’s bruises
During Ventura's testimony, prosecutors showed jurors photos of bruises on Cassie's body from Christmas Eve in 2011.
"She was bruised, and I wanted to make sure we memorialized it," Ventura said of taking the photos. When asked by prosecutors how her daughter got the bruises, Ventura alleged "she was beaten by Sean Combs." The photos were taken in Cassie’s bedroom in Ventura’s Connecticut home, and it was the first time Cassie told her mom about the alleged violence in their relationship.
Ventura also recalled an intense confrontation from April 2011 when she was visiting Cassie in LA. They were at Combs' house with a group of people, including Mia, a former Combs assistant who is also a witness in the federal sex-crimes trial. Combs was upset that Mia was laughing, and Mia looked "shaken and afraid" while leaving the room, Ventura testified.
Cassie's mom Regina Ventura testifies that she wired Combs $20K
Ventura Fine's mother, Regina Ventura, said she first met Combs in 2006.
Prosecutors quickly asked her about an email her daughter mentioned while on the stand last week. In the message, sent on Dec. 23, 2011, Ventura Fine confessed to her mother that Combs was threatening to release a sex tape of her on Christmas Day. Around the same time, Ventura Fine told her mother about the alleged physical abuse she was facing from Combs.
Ventura told the courts, "I was physically sick" over the threats to hurt her daughter and the tapes.
Then, Ventura said she was told she needed to wire $20,000 to Combs: "He was angry that he spent money on her (Cassie) and that she had been with another person." Ventura took money from her home equity loan and wired the funds to Combs’ company.
She said the money came back four to five days later. When asked by federal prosecutors why she wired the money, Ventura said "I was scared for my daughter’s safety." Ventura testified that she was ordered to "pay Sean Combs because he demanded it."
Diddy's former assistant recalls undergoing security checks, lie detector tests
James, on May 20, recalled an incident when Ventura Fine's bracelet from the luxury jewelry brand Cartier went missing. He was pressured to take a polygraph test and let Combs' other employees search his belongings as they looked for the jewelry.
It wasn't the first time James said he felt he had to defend himself: On two other occasions, James testified he felt he had to take lie detector tests. The first came after the aide said Combs had a significant amount of cash go missing.
"It was very intimidating," James told the court, but he felt he couldn't say no. "Not if I wanted to keep my employment with Mr. Combs."
On another occasion about six to eight months later, one of Combs' watches went missing. The lie detector test operator would later tell James, "You look very nervous," he testified. James said it was because he had taken some alcohol and clothing from Combs' homes without him knowing.
Former Combs staffer says 'my life was in danger' in Suge Knight incident
James testified that he ended his employment with the rapper following a November 2008 incident that made him fear for his safety.
James said that he and Combs' longtime friend known as D-Roc were sent to pick up food for Combs at a diner, where they encountered Suge Knight, one of Diddy's top competitors in the music industry. According to James, D-Roc walked over to Knight and identified himself as "Biggie’s boy," to which Knight asked, "What (are) you doing in my city?" Knight was referring to Los Angeles, where he came up in hip-hop.
James said he and D-Roc ordered food, but while waiting, they saw four black SUVs pull up, and someone walked over and handed Knight a gun, James said.
After returning to Combs’ house, Combs made James drive him and D-Roc back to the diner, and the rapper had three handguns in his lap, James said. But when they arrived, the black SUVs were no longer there, and they soon went home. James testified that he was "really shook up" by the experience and that this was the first time he felt that "my life was in danger" while working for Combs.
James, who ended his employment with Combs in May 2009, also recalled seeing Cassie crying and telling him not to go back to the diner.
Former Combs staffer details picking up drugs, including Barack Obama-shaped ecstasy
On the stand, James alleged that part of his job was picking up drugs for Combs and the ex-mogul’s friends, including prescriptions for the opioid Percocet from the pharmacy and one instance where he picked up large amounts of cocaine from a yacht in St. Tropez.
In another instance, James testified that he got ecstasy from Combs’ medicine bag for one of his friends. The rapper had several different types of ecstasy pills, including "one in the shape of a former president’s face," James said, later clarifying that it was shaped like former President Barack Obama.
During the testimony, Combs took notes on his lap and nodded his head when James was speaking about him being an involved businessman
Former personal assistant implied Diddy kept footage of him
Recalling a New Year’s Eve party when he was invited to celebrate at Combs’ house, James said he took ecstasy out of his boss’ bag without permission and consumed it alongside Ciroc, an alcohol brand Combs had heavily promoted.
"I was feeling pretty good," he said. "I’m normally pretty straight edge, but I was dancing … I was just vibing. I was enjoying myself." A few days later, when Combs was reviewing footage of the party with James there, he said his boss asked: "Yo playboy, was that you dancing around the party?" He said yes and confirmed he has taken ecstasy.
"OK, I’ll keep this footage in case I ever need it," James recalled Combs telling him. When asked by prosecutors what he believed Combs meant by it, James said he assumed that Combs would release it one day if he ever wanted to embarrass him.
David James details hotel night in Miami
James testified that in his job as a personal assistant, he was often asked to set up hotel rooms for Combs.
"I don’t think Mr. Combs ever stays alone," he said, recalling one night in Miami in 2008 in which he was asked to bring an iPad to Combs’ hotel room. When he knocked on the door, there was no answer, so he let himself in, James said.
He testified that he saw Ventura Fine on the bed with the comforter up to her neck, "not moving." Noting that she always slept on her side, James said it seemed unusual to him that she was on her back. There was also a naked man with long hair and "a very large abdomen" in the room, who scurried away when James entered, he said. He also testified he heard water running and that Combs was in the shower.
Asked whether he ever spoke to Combs or Ventura Fine about what happened he said, "I didn’t think it was my business. I don’t have conversations with Cassie or Mr. Combs about their personal affairs."
Cassie's mom Regina Ventura to take the stand
One witness expected to take the stand for prosecutors is Regina Ventura, Ventura Fine's mother.
Ventura Fine opened up in her own testimony about what her mother did and didn't know about her relationship with Combs – and the alleged abuse she faced.
After Combs found out about Ventura Fine's relationship with Kid Cudi in 2011, Ventura Fine told her mother and Combs' assistant, Capricorn Clark, about Combs' threats of releasing explicit footage of her in retaliation using an alias email. Ventura Fine said Combs also vowed to hurt both her and the rapper. The court saw photos of the large bruises she had on her lower back and thigh, taken at the time.
At the time of the threats, Ventura Fine had returned home to Connecticut to visit her mom for Christmas. She told her mom the bruises were from the first time Combs had assaulted her, even though the alleged assaults had been going on for years. She "was terrified" to tell her mom, Ventura Fine said.
Kerry Morgan alleges Combs assaulted her with a wooden hanger
Morgan testified that her friendship with Ventura Fine ended after Combs assaulted her in April 2018.
Cassie's former friend said she was listening to the singer's music in Ventura Fine's Hollywood Hills house before Combs came in and allegedly choked Morgan, adding that Combs was yelling and accusing Ventura Fine of cheating on him. She said the rapper "boomeranged" a wooden hanger at her head, which hit her behind the ear.
Dawn Richard recalls celebrity-packed dinner where Diddy punched Cassie
Under cross-examination, Richard told the court about a dinner around 2009 where she allegedly saw Combs punch Cassie. She told the court that music industry heavyweights such as Usher, Jimmy Iovine and Ne-Yo were in attendance.
Richard said she frequently saw Combs physically abuse Ventura Fine between 2009 and 2011, recalling injuries on her face, arms and knees. She also said she was "shocked" and "scared" after Combs threatened her, warning that "if we said anything, we could go missing" and "we could die."
Why is Diddy on trial?
Combs is facing federal sex-crimes and trafficking charges in a sprawling lawsuit that has eroded his status as a power player and kingmaker in the entertainment industry.
He was arrested in September 2024 and has been charged with racketeering, sex trafficking and transportation to engage in prostitution. He has pleaded not guilty to all five counts.
What is racketeering?
Racketeering is the participation in an illegal scheme under the Racketeer Influenced and Corrupt Organizations Statute, or RICO, as a way for the U.S. government to prosecute organizations that contribute to criminal activity.
Using RICO law, which is typically aimed at targeting multi-person criminal organizations, prosecutors allege that Combs coerced victims, some of whom they say were sex workers, through intimidation and narcotics to participate in "freak offs" — sometimes dayslong sex performances that federal prosecutors claim they have video of.
Where can I watch the Diddy trial?
The trial will not be televised, as cameras are typically not allowed in federal criminal trial proceedings.
Paste BN will be reporting live from the courtroom.
Contributing: Paste BN staff; Reuters
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