The Grammy-winning singer, songwriter, and actor known as Kid Cudi is expected to testify in the on-going sex-trafficking trial of the music producer Sean “Diddy” Combs this week and answer questions about an affair he had with Mr. Combs’s ex-girlfriend, Cassandra Ventura, and possibly about his Porsche, which was set on fire in 2012. Mr. Combs has long denied any involvement in the car incident.  

On Wednesday, Ms. Ventura’s mother, Regina Ventura, who was called to the witness stand, told the jury about an email message she received from her daughter on December 23, 2011, saying she’d been threatened by Mr. Combs after he found out about her affair. 

“I was physically sick,” Ms. Ventura’s mother said as she described how she felt after having read the email. “I did not understand a lot of it. The sex tapes threw me … I knew that he was going to try to hurt my daughter.” When asked by the prosecution who “he” was, she said, “Sean Combs.” 

Ms. Ventura testified last week that she wrote the email message to her mother and to one of Mr. Combs’s assistants while she was on an airplane on her way to spend Christmas with her family in Connecticut, where she was born and raised. 

Mr. Combs, she alleged, was threatening to publish sex tapes of her having sex with various men, including male prostitutes, which he recorded during his so-called Freak Off sex parties. According to Ms. Ventura, he had threatened to publish the tapes either on Christmas day or shortly before or after. Mr. Combs was furious, she said, after he had found out she was seeing Kid Cudi, whose real name is Scott Mescudi. 

Questioned by the defense, Ms. Ventura said that Mr. Combs had introduced her to Mr. Mescudi so she could record a song with the multi-platinum rapper. Then, during one of his Freak Offs, while looking through her phone without her permission, she said, he found out about the affair.  

In her email message, Ms. Ventura wrote that Mr. Combs “also said that he will be having someone hurt me and Scott Mescudi physically (he made a point that it wouldn’t be by his hands, he actually said he’d be out of the country when it happened).”  

The sex tapes were never published. However, Ms. Ventura’s mother testified that “it was understood that he was going to need $20,000 to recoup money that he had spent on her because he was angry that she had a relationship with Scott Mescudi.” 

The mother, who was “scared” for her daughter’s “safety,” took out a home equity loan and wired the money to Mr. Combs. Days later, the money was wired back without an explanation.

Ms. Ventura testified that Mr. Mescudi came to see her in Connecticut over the holiday and that she ended the affair, fearing Mr. Combs could hurt her and Mr. Mescudi. According to Rolling Stone, which cited police records and the Los Angeles Fire Department, Mr. Mescudi’s Porsche was set on fire by an “incendiary device” on January 9, 2012, at a Los Angeles address connected to him through public records. No one was charged, and Mr. Combs denied any involvement in a statement through his attorneys.  

Last Wednesday, Ms. Ventura told the jury about a meeting in Los Angeles with Mr. Mescudi and Mr. Combs. “The purpose of the meeting was to discuss the relationship that we were no longer in,” she said, referring to the affair she had ended with Mr. Mescudi. “Scott said, ‘What about my vehicle?’ And Sean said, ‘What vehicle?’”

Mr. Mescudi will undoubtedly be questioned about that meeting during his upcoming testimony. If federal prosecutors can prove to the jury that Mr. Combs set his car on fire, they would have one of two acts needed to convict the defendant of racketeering conspiracy. 

Racketeering conspiracy, also known as Racketeer Influenced and Corrupt Organization Act, alleges that individuals agreed to participate in a criminal enterprise to commit a pattern of illegal activities. Unlike general conspiracy charges, which focus on a single criminal act, racketeering conspiracy involves a series of crimes committed over time as part of a broader operation. 

In the indictment, federal prosecutors list several “purposes of the Combs enterprise.” One of them alleges, “Preserving, protecting, promoting, and enhancing the power of the Combs Enterprise, including the power of its leader, COMBS, through violence, use of firearms, threats of violence, coercion, and verbal, emotional, physical, and sexual abuse. …”  

“When employees, witnesses to his abuse, or others threatened COMBS’ authority or reputation,” the indictment also states, “COMBS and members and associates of the Enterprise engaged in acts of violence, threats of violence, threats of financial and reputational harm, and verbal abuse. These acts of violence included arson. …”  

In addition to the RICO charge, the 55-year-old music mogul is also charged with sex trafficking and transportation to engage in prostitution. He has pleaded not guilty and is facing the possibility of a life sentence behind bars.

On Wednesday, prosecutors also called Sharay Hayes, 51, a male exotic dancer, whose stage name is “the Punisher.” Mr. Hayes testified that he was hired by Mr. Combs and Ms. Ventura in 2012 about eight to 12 times, and met the couple at various hotels in New York, including the Trump International Hotel.    

At the first meeting, he thought he’d been hired to strip and dance. Instead he was asked to rub baby oil on Ms. Ventura, while Mr. Combs watched and pleasured himself. Contrary to the testimony of another male stripper, who testified last week, Mr. Hayes said the couple did not appear to be using drugs. 

He also said that he did not know that the man was Mr. Combs, “What I recall is the man was nude, but I could not see his face. There was, like — I don’t know what it was called, it was, like, what the Muslim women wear, where the face is covered completely in the veil and you can only see the eyes. It was a nude male with one of those veils on. And I could see he had what I — what I saw as a bottle of Astroglide he was carrying. “ 

Eventually Mr. Combs exposed his face, the exotic dancer said, adding that Mr. Combs would also give directions for the dancer to have sex with Ms. Ventura. 

“One time we were actually having sex and he dropped like a stack of money on the bed, and he said … ‘I like this s—’. So he would give feedback in terms of his being happy with the scenario,” Mr. Hayes testified. He also told the prosecution that he was paid about $800 for his sexual performances, thus establishing that Mr. Combs was engaging in solicitation of prostitution.

The last time Mr. Hayes was hired by the couple, he said, was in 2015 and he “couldn’t perform.” 

“Mr. Combs came … he threw condoms on the couch, and he expressed he was ready for us to begin penetration. His interaction and him being in close proximity was not the norm, so it kind of threw me off and startled me, so I struggled with getting an erection and I couldn’t perform.” 

Prosecutors also asked about a book Mr. Hayes wrote in 2022, which is called “In Search of Freezer Meat.” The author described it as a “men’s self-help book that chronicles me and developing and ultimately curing my erectile dysfunction by way of a penis implant.” 

Mr. Hayes told the jury that his sexual encounters with Mr. Combs and Ms. Ventura are described in the book in “six-and-a-half” pages. The jury even saw images from the book, and learned that Mr. Hayes had called Mr. Combs and Ms. Ventura the “married wealthy couple.”

Last but not least, prosecutors called an FBI agent to the stand. A special agent with Homeland Security Investigations, Gerard Gannon, said he was assigned to the unit that conducted the search of Mr. Combs’s Miami Beach home on March 25, 2024. Nearly 100 law enforcement agents were present, he said, because of the size of the property. 

Mr. Gannon testified that agents found parts of AR-15s with their serial numbers scratched off and two loaded magazines and receivers inside of closets next to platform shoes, sex toys, baby oil, lubricant, and lingerie. 

Mr. Gannon’s testimony will resume on Wednesday. Prosecutors also plan to call a clinical psychologist, Dawn Hughes, and a former employee of Mr. Combs, George Kaplan, who says he quit after witnessing how his boss physically abused Ms. Ventura. 

After Mr. Kaplan’s testimony, Kid Cudi is expected to take the stand.