Diddy trial latest updates: Kid Cudi expected to testify after Trump Tower ‘freak off’ detail revealed by male escort ‘The Punisher’ Sharay Hayes

Cassie’s mom took the stand yesterday. But who are the Venturas?
Regina Ventura, the mother of Sean Combs’s ex-girlfriend Cassie Ventura, delivered testimony Tuesday.
During her quarter of an hour at the witness stand, the elder Ventura testified that Combs became angry when he discovered her daughter was dating rapper Kid Cudi in 2011.
Cassie has been supported by loved ones throughout the trial, including her husband, Alex Fine, who was a mainstay in the courtroom while she testified last week.
Reporting from New York, Isabel Keane details what we know about the star witness’s family:
James Liddell21 May 2025 10:36
Diddy ‘brought three handguns’ to confront Suge Knight at LA diner
Sean “Diddy” Combs brought three handguns to a famous diner after learning that his record executive rival Suge Knight would be there, the music mogul’s former personal assistant testified Tuesday.
David James, who worked for Diddy from May 2007 through May 2009, told a New York federal court Tuesday about an incident from November 2008 at Mel’s Drive-in, a famous diner chain in Los Angeles.
On the November 2008 night, James and D-Roc, Diddy’s security guard, drove to get their boss cheeseburgers around 3 a.m. one morning. When they arrived at the diner’s parking lot, D-Roc noticed just three parking spots away was Knight, then-CEO of Death Row Records and one of Diddy’s “competitors,” James testified.
Kelly Rissman, who was at Tuesday’s hearing, has the details:
James Liddell21 May 2025 10:32
Recap: What happened in yesterday’s hearing?
Sean “Diddy” Combs’s sex trafficking trial entered its seventh day of Testimony Thursday and began with his former assistant, David James, returning to the stand.
James, who worked for Combs between 2007 and 2009, recounted feeling afraid for his life while driving with Combs to a diner where he had spotted his rival, Suge Knight. Combs had three handguns with him as he rode in the backseat, James testified.
Cassie Ventura’s mother, Regina Ventura, testified next.
Regina said that Combs became angry when he discovered her daughter was dating rapper Kid Cudi in 2011. Combs then wanted to “recoup” the money he spent on Cassie and demanded $20,000 from her family, or else he’d release explicit footage of her, Regina testified.
The elder Ventura said she took out a home equity loan to make the payment. The money ended up back in Regina’s account a few days later, but Combs never spoke to her about it, she testified.
Sharay Hayes, a male exotic dancer known as “The Punisher,” then testified about his “freak-offs” with Combs and Cassie. Hayes said he never sensed any discomfort from Cassie, adding that he never saw Combs film her or hurt her.
The day ended with testimony from special agent Gerard Gannon, who was involved in the raid on Combs’s Florida mansion last year. Gannon testified that officials found AR-15 rifle parts, bottles of baby oil, sex toys and platform high heels inside a bedroom closet.
James Liddell, Katie Hawkinson21 May 2025 10:25
Kid Cudi expected to take stand today
Scott Mescudi, better known as the rapper Kid Cudi, is set to testify in Sean “Diddy” Combs’s New York sex trafficking trial later this week.
In 2011, Mescudi dated Casandra “Cassie” Ventura, Combs’s on-and-off girlfriend for over a decade. Now, the Day ‘N’ Nite singer will be testifying in Manhattan federal court on Wednesday or Thursday.
Last week, Ventura testified that Combs abused her after learning about her relationship with Mescudi. The prosecution’s star witness told jurors that Combs lunged at her with a wine bottle after he found emails between her and Mescudi during a “freak off.”
Katie Hawkinson has outlined what witnesses have said about Mescudi so far:
James Liddell21 May 2025 10:18