The second week of Sean ‘Diddy’ Combs’ trial in Manhattan is drawing to a close. Various witnesses have taken the stand against the music mogul, including hotel staff, Regina Ventura (Cassie Ventura’s mother), and Diddy’s former personal assistant.
The trial kicked off on Monday, May 12, following an earlier week where Cassie Ventura, Combs’ former partner, faced extensive questioning regarding the rapper-producer. Combs was arrested last September in New York on charges including racketeering and sex trafficking by force, fraud, or coercion. He has consistently denied these allegations and entered a plea of not guilty.
Cassie claimed that Combs forced her into ‘freak-off’ parties, involving her having sex with a male escort while he observed, and cited multiple instances of physical abuse.
She also testified about Combs’ alleged substance use, including an apparent overdose at the Playboy Mansion in 2012. She mentioned that ecstasy or MDMA were his preferred drugs and that she saw him taking opiates daily.
Throughout this week, rapper Kid Cudi shared his experience in court regarding a confrontation with Sean ‘Diddy’ Combs after a break-in occurred at his home post his romantic involvement with Ventura.
Cudi, whose real name is Scott Mescudi, recounted dating Ventura in 2011, under the impression that she and Combs had parted ways. He recalled an incident where, after receiving a distress call from Ventura, he discovered his home security cameras altered, gifts opened, and his dog confined in a bathroom.
Cudi alleged Combs was responsible for the break-in and later was informed that his car had been set on fire. When Cudi confronted Combs, he denied involvement, stating: “I don’t know what you are talking about.” A few years later, Combs reportedly said to Cudi, “I’m just sorry for all that bullsh*t.” Ventura testified that Combs had assaulted her upon learning of her involvement with Cudi and even threatened that Cudi’s car would be blown up.
Ultimately, Cudi decided to end the relationship, citing escalating drama and safety concerns for both himself and Ventura. “I just felt things were getting out of hand,” he shared.
Frédéric Zemmour, the general manager of L’Ermitage in Beverly Hills, also took to the stand, allegedly reading from notes about Diddy. One note described, “ALWAYS spills candle wax on everything and uses excessive amounts of oil. Likes the room HOT! Please set thermostat to 75 degrees.” Cassie corroborated this, explaining how Combs would request a ‘freak off’ room with scented candles and oil, which she had to warm up.
Zemmour added that Diddy often booked rooms under aliases like ‘Ryan Lopez’ or ‘Frank Black,’ with the latter appearing on a pill bottle during a police raid on his hotel room. Despite these pseudonyms, staff reportedly recognized him and ensured specific room assignments.
Zemmour further claimed that hotel staff were instructed to mark the room ‘out of order’ following Combs’ stays for thorough cleaning, and once Combs received a $500 penalty for extensive candle wax damage.
Ventura’s prior relationship with musician Kid Cudi was brought up, including Diddy’s alleged anger over her dating another industry figure. This jealousy purportedly led Combs to demand $20,000 from Regina Ventura for a sex tape featuring her daughter, Cassie. “I was physically sick,” Regina Ventura said to The Independent, explaining her distress and comprehension that Combs aimed to harm her daughter.
Regina claimed she obtained a loan to pay off Diddy and thus prevent the tape’s release. She wired the money, only for it to return to her account days later. The incident was never revisited between them.
Regina also testified about photographing bruises on Cassie during a visit to her Connecticut home for the holidays in 2011. “She was bruised and I wanted to make sure we memorialize it,” she explained to the jury, expressing concern for her daughter’s safety.
Diddy’s former personal assistant, David James, who was employed by him between 2007 and 2009, shared his experiences, recounting a moment he feared for his life. This involved an alleged encounter with Suge Knight, a rival record producer, at Mel’s Diner in Hollywood when he and Diddy’s security guard D-Roc were collecting food.
Suge Knight, currently serving a 28-year sentence for voluntary manslaughter, co-founded Death Row Records, which had a notorious rivalry with Combs’ Bad Boy Records. In court, prosecutor Slavik asked James about an ‘incident at Mel’s Diner with Suge Knight.’
James recalled driving a silver Navigator to the diner for cheeseburgers when D-Roc identified Knight. They reportedly noticed four SUVs in the parking lot, and James saw someone hand Knight a gun, prompting a swift departure. They returned to the house to find Cassie crying and Combs joining them in the vehicle with three guns visible on his lap. Returning to the diner, they found Knight had left, but Combs instructed continued patrols of the area.
James chose to leave the company, saying, “They offered me other positions. But I just wanted to leave – my life was at risk.”
Sharay Hayes, known as The Punisher, spoke in court about his alleged involvement in Diddy and Cassie’s sex life. He claimed to be hired for ‘freak offs’ between eight to twelve times after meeting the couple in 2012, with the last encounter in March 2015, where he described creating a ‘sexy scene’ with Cassie at Diddy’s request, involving mutual application of baby oil.
He testified receiving $1,200 or $2,000 per session and engaging in sexual activity with Cassie under Diddy’s watch and instruction, with each encounter lasting about four hours. He was told not to acknowledge Diddy during these sessions, and Ventura allegedly thanked him for ‘respecting their privacy.’
On Wednesday, May 21, Homeland Security special agent Gerard Gannon continued his testimony concerning a search warrant for Diddy’s properties in Star Island and Los Angeles. In March 2024, 80 to 90 federal agents used an armored vehicle to access the Star Island estate. Items such as lingerie, lubricant, condoms, weapons, and more were reportedly found, with over 500 images from Combs’ Miami mansion released by the Southern District of New York documenting the search results.
Gannon detailed images showing high heels and sexual items, three cell phones hidden in boots, and 31 bottles of Astroglide, 25 containers of baby oil, firearm parts, and a Gucci bag with a crystal-like substance.
No images of Combs with firearms were found, but various pills, nitrous oxide canisters, and marijuana labeled with ‘Diddy’ were discovered. Bathroom mirror messages included ‘What do you WANT?’ and ‘You a legend.’
Prosecutors shared images from Combs’ Manhattan hotel room, where they allegedly found clonazepam, two bags of pink powder (one testing positive for ketamine, the other a mix of MDMA and ketamine), and approximately $9,000 in cash, suggesting preparations for a drug-fueled ‘freak-off.’
Richard, once signed to Diddy’s Bad Boy Records label from 2005 until 2011, claimed to have witnessed Ventura enduring assaults by Combs. Prosecutor Christy Slavik stated Richard saw Combs drag, kick, and punch Ventura. When asked what prompted these alleged attacks, Richard suggested they occurred when Ventura ‘would speak up for herself.’ Two members of Combs’ security team reportedly witnessed these incidents.
Richard added that Ventura suffered hits on ‘her knees, her face,