Phillip Pines, a former executive assistant to Sean “Diddy” Combs, has come forward with allegations that the rapper pressured him into having sex with a woman as a means of proving his “loyalty” during his time working for the music mogul.
Pines, who claims to have worked for Combs from 2019 to 2021, recounted the incident in a pre-recorded interview that aired after the final episode of the documentary series The Fall of Diddy.
According to Pines, during a party hosted by Combs, the rapper approached him while he was drinking alcohol and made an unusual request. “I remember hearing the words: ‘Prove your loyalty to me,'” Pines recalled in the interview.
Combs allegedly grabbed Pines by the shoulders, offering him a brief, almost coach-like massage, before handing him a condom and pushing him toward a woman seated on the couch. While Pines noted that the woman consented to the interaction, he said he felt pressured to go along with it, partly due to fear of potential repercussions from Combs.
In the interview, Pines described Combs as someone with a manipulative ability to make people feel at ease and get them to do things they would normally never consider. “He had control. It was a circus. He did whatever he wanted, and we were at his disposal,” Pines said. “He’s a predator. I mean that in a sexually manipulative way. He knows how to make you comfortable and make you do things for him that you never would have done otherwise.”
Pines also denied attending any of Combs’ so-called “freak-off” parties, which are expected to be referenced in the rapper’s upcoming trial, where he faces charges related to sex trafficking, racketeering, and forced prostitution.
However, Pines claimed he was involved in supplying materials for Combs’ alleged “Wild King Nights,” events that he says took place in hotel rooms and involved young women.
“We would get a laundry list of things: alcohol, marijuana, ketamine, Molly, mushrooms, baby oil, AstroGlide, candles, incense, Apple TVs, and electronics,” Pines detailed. “There were also male libido supplements and things like that.”
He explained that many of the women involved in these events were younger and less influential, making them more susceptible to Combs’ manipulations. “A lot of times, he would be with a young woman, and there was a power dynamic. These girls were more impressionable and easier to reel in, as opposed to someone who might resist or have their own public status,” Pines said.
In December 2024, Pines filed a lawsuit against Combs, accusing him of sexual battery, sexual harassment, sex trafficking, and other charges. Pines also alleged that he was tasked with cleaning up blood and bodily fluids after Combs’ parties, leaving generous tips for hotel staff in hopes of preventing any damage from being reported.
In response to the allegations, Combs’ representatives issued a statement reaffirming the rapper’s stance that he has never sexually assaulted or trafficked anyone. “No matter how many lawsuits are filed, it won’t change the fact that Mr. Combs has never sexually assaulted, or sex trafficked anyone—man or woman, adult or minor,” the statement read.
“We live in a world where anyone can file a lawsuit for any reason. Fortunately, a fair and impartial judicial process exists to uncover the truth, and Mr. Combs is confident he will prevail in court,” the statement continued.
