Diddy's trial is well into its second week, with new witnesses taking to the stand in Manhattan, New York.
Sean ‘Diddy’ Combs’ trial officially began on Monday (May 12), and last week, his former partner Casandra Ventura, known as Cassie, was questioned extensively about the rapper-producer.
Combs was arrested last September while he was in New York, accused of racketeering and sex trafficking by force, fraud or coercion, among other charges.
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Combs has repeatedly denied all the charges against him and has pleaded not guilty.
Cassie alleged Combs forced her to participate in so-called 'freak-off' sex parties, which she claimed involved her having sex with a male escort while he watched on, as well as several instances of physical violence.
She also spoke about Combs' alleged drug use, including a supposed overdose at the Playboy Mansion in 2012, and stated his 'drugs of choice' were ecstasy or MDMA and that she witnessed him consume opiates daily.
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This week has seen Cassie's mom Regina Ventura, Diddy's former PA David James, and singer Dawn Richard all take to the stand.
Here's what they had to say...
Dawn Richard alleged disturbing act Diddy did to Cassie
Richard, who was signed to Diddy's Bad Boy Records label from 2005 until 2011, alleged to have witnessed Ventura being assaulted a number of times by the producer.
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Prosecutor Christy Slavik said per Inner City Press more about what she claims to have observed.
Richard claimed: "He would drag her and kick her and punch her in the mouth."
She was then asked to clarify what she believed prompted the 55-year-old to allegedly beat Ventura when they dated, to which she claimed would occur 'when she would speak up for herself'.
Richard was further quizzed on who saw these attacks, to which she explained two members of the disgraced producer's security team.
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She added that Ventura would get hit on 'her knees, her face, all over'.
She then described an incident she said occurred during a music festival in Central Park, while she was at Combs' residence.
Richard testified: "He punched Cassie. She came into the bathroom crying... she was hurt," before Combs’ lawyer objected and the judge sustained it.
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Richard also claimed she saw Cassie with a swollen eye and once witnessed Combs allegedly slap her to tell her to 'shut the f*ck up'.
She said she feared for her safety and never intervened, adding, "If he did that to someone he supposedly loved, what would he do to an employee? So I'd approach Mr. Combs with softness."
Ventura's mom said Diddy demanded $20,000 for daughter's sex tape
While on the stand, Ventura's former relationship with fellow musician Kid Cudi was referenced and how Diddy was supposedly enraged about her dating someone else in the music industry.
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As a result of his jealousy, he allegedly demanded $20,000 from Regina Ventura, Cassie's mom, for a sex tape with the Honey 3 actress in it.
"I was physically sick," Regina Ventura claimed, as per The Independent. "I did not understand it, the sex tape threw me. He was trying to hurt my daughter."
Regina said she proceeded to take out a loan to be able to pay off Diddy and stop the tape's release. She allegedly wired the cash over to him, but said it ended up back in her account a few days later.
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She claimed the matter was never discussed between the pair again.
Ventura's mom also spoke of the photographs she took of the bruising she saw on her daughter when she visited mother’s home in Connecticut for the holidays in 2011.
"She was bruised and I wanted to make sure we memorialize it," Regina said of the pictures that have been shown to the jury. "I was scared for my daughter’s safety."
Diddy's former PA claimed he 'feared for his life'
Diddy's former PA David James - who worked closely with him between 2007 and 2009 - also took the stand, and testified about a moment where he said he feared for his life.
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That moment that James claims happened occurred when he and D-Roc, one of Combs' security guards, allegedly encountered rival record producer Suge Knight in Mel's Diner in Hollywood while picking up food.
Knight, who is currently serving a 28-year prison sentence for voluntary manslaughter in a fatal 2015 hit-and-run case, co-founded Death Row Records - which was in a bitter rivalry with Combs' Bad Boy Records.
In court, prosecutor Slavik asked James if there was an 'incident at Mel's Diner with Suge Knight'.
James replied: "Yes. I drove the silver Navigator to get cheeseburgers there. D-Roc said, 'That's motherf*cking Suge Knight'.
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"He went over and said, 'What's up?' Suge didn't recognize him. D-Roc said, 'I'm Biggie's boy'."
James continued: "We noticed four black SUVs to different sides of the parking lot. I saw someone hand Suge Knight a gun. D-Roc said, 'We gotta get out of here'. We drove back to the house."
When asked what they found upon returning, James said: "Cassie was crying. Mr Combs got in the vehicle.
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"I saw three guns on his lap. I felt calm because we'd been in a silver vehicle, now a black one - they wouldn't see us coming." He claimed that when they got back to the diner, Knight and his entourage were gone, but Combs instructed them to continue driving around the block to look for him.
James ultimately decided 'to leave the company,' adding: "They offered me other positions. But I just wanted to leave - my life was at risk."
Male escort told the court what really happened at 'freak-off sessions'
A male escort known as The Punisher - real name Sharay Hayes - spoke to the courtroom and gave alleged details about Diddy and Cassie's sex life and how he was involved.
Hayes claimed that he was hired between eight and twelve times for additional freak offs after first meeting the couple in 2012, telling the court the last one happened in March of 2015.
He said: "She explained to me that her and her husband liked to create a sexy scene that consisted of me and her mutually applying baby oil, applying it to ourselves and to possibly each other, and try to create a sexy environment that her husband would eventually come out to watch."
He testified that he usually received $1,200 or $2,000 after each session and said he wondered why the amount varied at times.
Hayes also alleged that he eventually engaged in sexual activity with Cassie while Diddy watched and often gave instructions. He said that the encounters would last about four hours.
Speaking about how Diddy was involved, he claimed: "I was specifically told to not acknowledge her husband, try not to look at him, no communication or anything.
“[Diddy] would at some point come into the room, sit in the distance, gave subtle directions to Ms. Ventura based on... angles, lighting, positionings, and sometimes the sexual activity.”
Hayes said his last encounter with the former couple saw Ventura allegedly pay him and thank him for 'respecting their privacy in terms of [their] interactions'.
'Freak-off' items found in Diddy's home and hotel room
On Wednesday (May 21), Homeland Security Investigations special agent Gerard Gannon resumed his testimony, speaking about a search warrant that had been obtained to enter Diddy's properties in Star Island and Los Angeles.
In March 2024, some 80 to 90 federal agents used an armored vehicle to breach the gates of the Star Island estate. Gannon previously testified that items such as lingerie, lubricant, condoms, and weapons were discovered during the search. The Southern District of New York later released more than 500 images from Combs’ Miami mansion, documenting the findings.
Gannon described several of these images in court. One showed high heels and sex items in the master closet; another revealed three cell phones hidden in a pair of boots.
Authorities also seized 31 bottles of Astroglide, 25 containers of baby oil, firearm components, and a Gucci bag containing a crystal-like substance.
Though no photos of Combs with the firearms were found, various pills, nitrous oxide canisters, and marijuana - labeled with 'Diddy' - were also discovered.
Messages written on a bathroom mirror included phrases like 'What do you WANT?' and 'You a legend.'
Prosecutors also released 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 about $9,000 in cash, which they claim points to preparation for a drug-fueled 'freak-off'.
What Combs' attorney has said
In response to the news of Combs' arrest last year, his attorney Marc Agnifilo told UNILAD at the time: "We are disappointed with the decision to pursue what we believe is an unjust prosecution of Mr. Combs by the U.S. Attorney’s Office.
"Sean 'Diddy' Combs is a music icon, self-made entrepreneur, loving family man, and proven philanthropist who has spent the last 30 years building an empire, adoring his children, and working to uplift the Black community. He is an imperfect person, but he is not a criminal.
"To his credit Mr. Combs has been nothing but cooperative with this investigation and he voluntarily relocated to New York last week in anticipation of these charges. These are the acts of an innocent man with nothing to hide, and he looks forward to clearing his name in court."
The trial is expected to last around eight weeks. If convicted, Combs faces up to life in prison.
UNILAD has previously contacted representatives for Combs and Ventura for comment.
The trial continues.
If you've been affected by any of the issues in this article, you can contact The National Sexual Assault Hotline on 800.656.HOPE (4673), available 24/7. Or you can chat online via online.rainn.org.
Ellie Kemp