A male escort who claimed he was handed stacks of cash to have sex with Casandra “Cassie” Ventura while Sean “Diddy” Combs watched gave detailed and explicit testimony about freak-offs with the hip-hop mogul on Monday, claiming he grew fearful of the “danger” Ventura was in and eventually feared for his life as well.
Daniel Phillip, 41, took the stand as the second witness for Southern District of New York prosecutors on the first day of Combs’ high-profile sex trafficking and racketeering trial. Combs — who pleaded not guilty to the five federal counts against him — turned and watched Phillip enter the courtroom and take his seat in the witness box.
Phillip described how he initially felt excited to be part of the couple’s bedroom fantasy after first meeting Combs and Ventura in approximately 2012. At the time, he was working as a manager for a male entertainment show when his boss called him and said a bachelorette party requested a Black male stripper. No one who fit the description was available, so Phillip said his manager asked him to fill in, to which he obliged, picking up an NYPD T-shirt as his costume.
However, upon his arrival at the luxury Gramercy Park Hotel in New York City, no bachelorette party was waiting inside. Instead, the “most beautiful woman I had seen” answered the door in a red wig, red lingerie, high heels, and dark sunglasses. Phillip said he later came to know the woman as Ventura.
Ventura allegedly told Phillip that it was her birthday and that her husband wanted to do “something special” for her to celebrate the occasion. Handing Phillip a stack of cash, Ventura asked if he’d be OK with them rubbing baby oil on each other and seeing where things went as her purported spouse watched.
Entering the dark and candlelit hotel suite, Phillip saw a robed man sitting in the corner of the room with a bandana covering his face and a baseball cap slung over his head. But once he heard the self-described “importer and exporter” talk, Phillip said he immediately recognized the man as Combs.
Over the next few years, Phillip said Ventura paid him for sex following encounters that could last upwards of 10 hours at hotels around New York City, Combs’ private midtown residence, and Ventura’s apartment in the city. Phillip described freak-offs as highly ritualistic. The rooms were always set up similarly, and Combs allegedly directed Phillip and Ventura’s every move, even down to instructing Phillip when to finish.
Phillip claimed Ventura paid him anywhere from $700 to $6,000 for the visits. But Phillip said he wasn’t in it solely for the money. “In my head, I was just excited that I was in this world and, you know, happy to be involved with people with such notoriety,” Phillip said. “I didn’t care if I got paid one way or another.”
However, Phillip testified that his enthusiasm waned the first time he claimed to witness Combs attack Ventura during a freak-off. Combs called for Ventura to come to the bedroom, but when she didn’t immediately comply, Phillip claimed Combs threw a liquor bottle in her direction, with the bottle smashing into the wall. Combs then allegedly dragged a screaming Ventura by her hair back to the room, where he heard sounds of slapping and Ventura apologizing, saying, “I’m sorry, I’m sorry!”
“Bitch, when I tell you to come here, you come now, not later,” Phillip claimed he overheard Combs tell Ventura. The two later exited the room, and Combs wanted the freak-off to resume, Phillip testified. “Are y’all ready to continue,” Combs purportedly asked. “It came out of nowhere,” Phillip told the court. “I was terrified. I didn’t know what to do.”
“My thoughts was that this was someone with unlimited power, and chances are that even if I did go to the police, that I might still end up losing my life,” Phillip added when questioned why he didn’t intervene or ever seek help from law enforcement.
After that incident, Phillip said he had trouble performing sexually during freak-offs with Ventura and Combs. During one moment, they were left alone in another freak-off; Phillip said he tried to warn Ventura of the “danger” that he perceived she was in, asking why she was staying with Combs when he was “hitting” her. Phillip said Ventura attempted to reassure him, saying she’d be OK.
There were other troubling moments, including when Phillip testified that he arrived for a freak-off only to see a seemingly incapacitated Ventura “passed out” on the couch, her body “half on the couch, half off of the couch.” Combs allegedly told Phillip, “I don’t think this is going to happen today.”
He claimed that sometimes, it appeared another person had been in the room before him with half-empty bottles of oil and lubricant strewn about. During at least one freak-off, Phillip said there was another male escort present having sex with Ventura.
Around two of the sexual encounters were recorded by Combs, Phillip said, and at one point into the arrangement, Combs took a photo of Phillip’s driver’s license and said something to the effect of, “It’s just for insurance, just in case.” Phillip said he “understood” the comment to be Combs “threatening me.”
During one freak-off, Phillip said he took the party drug Ecstasy, which made him feel both nauseous and euphoric at the same time. “I took that Molly, and then I became a totally different person,” Phillip said. “I went out into Times Square and I handed out hundred dollar bills to every single person that I saw in front of me.”
At one point during Phillip’s sexually explicit testimony, Combs’ three teenage daughters in attendance left the courtroom. They returned briefly while Phillip was still on the stand, only to leave for the rest of the day.
Phillip’s testimony followed the government’s first witness, former hotel security guard Israel Florez. Florez testified that he responded to a call in 2016 of a “woman in distress.” When he arrived, he saw Ventura looking frightened, and her hoodie was pulled over her head. Still, he could tell she had a “purple eye.” He added that Combs had a “devilish stare” on his face.
According to Florez, Combs offered him a wad of cash to keep quiet about what he witnessed. “Don’t tell nobody,” Combs allegedly ordered him, he said. Florez added that he didn’t call the police because “there was no victim there, obviously nobody was pressing charges.”
Ventura is expected to testify against Combs this week. In her opening statement, Assistant U.S. Attorney Emily Johnson said she’ll testify about the “dark hotel rooms” that Combs kept her in for days at a time, where she was allegedly forced to have sex with hired male sex workers. During these days-long “freak-offs,” Ventura was allegedly kept compliant and awake through a variety of drugs, including Ecstasy.
Combs’ attorney Teny Geragos argued in her opening statement that the case is not about sex trafficking but people’s motivations for coming forward after so many years. She argued that Ventura and another prosecution witness who claims Combs physically abused her were fully capable women who made choices because they had something to gain from being in a relationship with Combs. She told jurors that Ventura filed a civil lawsuit before reporting her alleged abuse to authorities. “Ask yourself why,” Geragos said. “The answer is money.” Geragos admitted that Combs was violent in his past relationships but did not engage in any sex trafficking.
This post was updated on Monday, May 12 at 9:53 p.m. to reflect full testimony from the witness.
