Diddy's ex-assistant exposes harrowing freak-off experience: Orders to prove ‘loyalty’ to the ‘king’ | New doc
The Fall of Diddy docuseries concludes on Tuesday. The rapper's ex-assistant Phillip Pines breaks silence on sexual battery allegations he levelled against him.
An ex-Diddy assistant has come clean about the disturbing scene at the disgraced hip-hop mogul Sean ‘Diddy’ Combs’ notorious freak-off parties. Inching closer to the finish line, the bombshell documentary The Fall of Diddy features Phillip Pines’ tearful account of the controversial rapper’s sex-filled gathering, suggesting that he was pushed to prove his “loyalty” to his boss in the worst way possible.
Combs’ former personal assistant recounted that Diddy once ordered him to have sex with a girl at one of his parties, referring to himself as the ‘King’ in charge of everything. Pines claims that he reluctantly complied and “performed for a bit” only to quickly slip out of the room when his boss - whose system was brimming with drinks and party fever - looked away.
Diddy and chief of staff had ex-assistant at their beck and call
Phillip Pines alleged that the ‘Bad Boy for Life’ and his chief of staff at Combs Enterprises, Kristina Khorram, had him set up a hotel room or a room in one of the rapper’s luxury homes for the so-called ‘Wild King Nights,’ which legal documents have so far referred the ‘Freak Offs.’
Preparations for these X-rated events would come with a ‘laundry list’ of things needed, including ketamine, marijuana, baby oil, mushrooms, male libido supplements and the lubricant Astroglide, among other things. Yet another responsibility entailed that he had to clean up after Diddy's freak-offs. He claims to have often been asked to do an “emergency cleanup,” which automatically meant that his boss had turned the room upside down.
Phillip Pines subjected to sexual battery during his time as a Diddy employee
Available from Tuesday night, the latest inclusion to Investigation Discovery’s The Fall of Diddy docu-series details a sickening experience Pines had to live through while he was on Diddy’s payroll. “My life changed and I've never really recovered from it,” he said of the uncomfortable moment when he had to “prove himself” to Diddy, especially since loyalty was “everything” to him. In a December 2024 lawsuit, Pines foregrounded that he worked for the disgraced rapper between 2019 and 2021. Pines accuses his employer of treating him “like an animal playing fetch in order to prove his loyalty.”
Digging into the events of the day, Pines recalled that his boss had been drinking all day while he was told to prepare things for the next stage of the party that involved even more alcohol and drugs. “I took a shot (drink) with them. That was his way of making sure you felt comfortable,” Pines began. “I remember hearing the words prove your loyalty to me, (your) King.”
“He grabbed me by the shoulders, gave me a massage like a coach would give a player that's about to enter the game, handed me a condom, pushed me to a girl that was on the couch, a guest.
“I froze before it took place, I didn't know what was happening. In the moment it felt like what, is this fun for him? Is this a test for entertainment, does he know he's doing this? Is he that gone?”
Diddy's ex-assistant complied out of fear for his well-being
A helpless Pines didn’t know what to do in the given situation. As the girl gave him consent, he claims to have “performed for a little bit,” later running “out of there as soon as I didn't see him in my sight anymore.”
Diddy’s former assistant has sued him for subjecting him to sexual battery and harassment, sex trafficking and other unwarranted demands. He outrightly labels him a “predator… in a sexually charged way, a manipulation way.”
In the new documentary interview, Pines admits that he feared speaking up about his harrowing experience as he had seen Diddy physically assaulting other employees who retaliated against his demands. He also described cleaning up the mess after the Wild King Nights as “one of the hardest things to do.”
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Harrowing insight into Diddy's freak-offs
“When you get there, you see the wreckage, the stains, the used condoms, the baby oil half used, Astroglide oozing down the sizes of the bottle and you have to pick it up. Broken glass, urine, blood, stains on the furniture,” he explained.
“I kid you not, you could slip because there was baby oil all over the floor. There would be baby oil surrounding the bathtub and there would be a bathtub full of water. You'd reach down to unplug and you'd feel the baby oil at the top.” He now confesses that the smell of baby oil has become a triggering reminder of all the disgusting things happening behind closed doors that one could “only imagine.”
The Revolt founder is currently behind bars, awaiting trial on sex trafficking and racketeering charges.
The Fall of Diddy finale will be available on ID beginning January 28 at 9 p.m. ET. After that, streaming options are Max and Discovery+. The upcoming exclusive 30-minute Phillip Pines interview expands the explosive four-part series. Journalist Mara S Campo conducted the sit-down with Combs' former senior executive assistant. It marks the first time he speaks up about his ex-boss's allegations on camera.
