Diddy’s Former Assistant Claims He Was Pressured to Have Sex for His Boss: “Prove Your Loyalty to Me”

While Sean “Diddy” Combs awaits trial on federal sex trafficking and racketeering charges, his former senior executive assistant Phil Pines, who worked for the hip-hop mogul from 2019 to 2021, is speaking out.

Pines’s bombshell interview with journalist Mara S. Campo concluded The Fall of Diddy, a new four-part Investigation Discovery docuseries containing allegations from Combs’s former friends, colleagues, and employees. “The reason I wanted to tell my story was to make sure that Sean Combs and people like him can’t do these kinds of things to anybody else,” Pines said in the bonus episode, which aired on Tuesday, January 28. “It’s hard to come here and sit down with you and talk about these situations, because he was somebody that I looked up to.”

Pines’s interview was filmed in New York City only last week, according to Investigation Discovery. It marks his first on-camera remarks since he filed a lawsuit against Combs last month, alleging that his former employer ordered him to supply drugs and sexual paraphernalia for, and later clean up after, parties called “Wild King Nights.” Diddy’s legal team addressed the filing in a statement to People at the time, saying, “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. We live in a world where anyone can file a lawsuit for any reason. Fortunately, a fair and impartial judicial process exists to find the truth, and Mr. Combs is confident he will prevail in court.”

During The Fall of Diddy’s final installment, Pines said that he wasn’t present for any of Combs’s “freak-offs”—the term allegedly used for days-long sex performances facilitated by various drugs. But Pines did claim that he was instructed to provide drugs, alcohol, sex toys, and lubricant like baby oil for what his boss allegedly called “Wild King Nights.” According to Pines, he would also be told to anticipate “emergency cleanup” after such events, meaning that Combs had “destroyed the hotel room,” said his ex-assistant. “That was, for me, probably one of the hardest things to do—when you get there and you see the wreckage.”

Later in the interview, Pines alleged that Combs once pressured him to have sex with a female participant at a “Wild King Night” after he had drank alcohol. “I remember hearing the words: ‘Prove your loyalty to me,’” said Pines. “He grabbed me by the shoulders, kind of gave me, like, a quick massage—like a coach would give a player that’s about to enter the game—and handed me a condom, pushed me to a girl that was on the couch, a guest.”

Pines said that the woman signaled her consent before their sexual encounter, which he agreed to in part to avoid potential retribution from Combs. After it was over, he “had a great sense of remorse,” Pines said, though he added that he didn’t tell anyone else about the alleged activity.

“I wanted to tell somebody, but there was so much at stake,” he said. “I knew if I had said anything that a kind of bomb would just explode. I hid that from everybody, including my significant other, my family, other employees.”

Vanity Fair has reached out to Combs’s legal representative for additional comment on Pines’s allegations. The following statement has been shared with multiple outlets regarding The Fall of Diddy: “These documentaries are rushing to cash in on the media circus surrounding Mr. Combs. The producers failed to provide sufficient time or details for his representatives to address unsubstantiated claims, many from unidentified participants whose allegations lack context. By withholding this information, they made it impossible for Mr. Combs to present facts to counter these fabricated accusations. This production is clearly intended to present a one-sided and prejudicial narrative. As we’ve said before, Mr. Combs cannot respond to every publicity stunt or facially ridiculous claim. He has full confidence in the facts and the judicial process, where the truth will prevail: The accusations against him are pure fiction.”

When asked about the allegation that producers did not give Combs’s reps enough time to respond to claims, an Investigation Discovery spokesperson told VF: “The Fall of Diddy uses firsthand accounts, in-depth interviews, and publicly available content to tell this timely story.”

Combs, whose trial is slated to begin on May 5, pleaded not guilty to the charges and has denied all allegations against him. “Mr. Combs has full confidence in the facts and the integrity of the judicial process. In court he will prevail: that the accusations against Mr. Combs are pure fiction,” his legal team said in response to the allegations included in the documentary.