January 29, 2025: In a shocking revelation, former Sean ‘Diddy‘ Combs assistant Phillip Pines opens up about the unsettling and dangerous atmosphere surrounding the infamous “Freak-Off” parties, providing a fresh perspective on the debauchery that has long surrounded the hip-hop mogul’s inner circle. In the latest installment of The Fall of Diddy documentary, Pines, who worked for Combs between 2019 and 2021, shares the disturbing details of the events he witnessed and the traumatic experiences he endured under the rapper’s command.
The documentary, which aired its final episode on Investigation Discovery on January 28, unveils the harrowing realities behind these notorious gatherings, offering a glimpse into the power dynamics, manipulation, and psychological trauma involved. Pines recounts the chilling pressure he faced to prove his loyalty to Combs in one of the most unsettling moments of his life.
“Prove Your Loyalty”: A Moment of Fear and Submission
In a tearful interview, Pines describes an incident at one of Diddy’s “Wild King Nights,” where he was instructed by his boss to have sex with a woman in front of party guests. Pines recalls Diddy, who had been drinking heavily, referring to himself as the “King” and demanding that everyone present show their loyalty.
Pines, who initially froze in confusion and fear, reluctantly complied, performing for a short time before escaping the room when Diddy’s attention shifted. “I didn’t know what was happening,” Pines confesses. “It felt like a test, like entertainment for him, but I was stuck—what could I do?”
In his emotional recounting, Pines emphasizes the psychological toll of being coerced into such a situation, suggesting that he was forced to prove his worth and submission in ways that left him deeply scarred. He was later instructed to clean up the aftermath, an ordeal he describes as “one of the hardest things to do.”
Disturbing Details Emerge About the “Freak-Off” Events
The documentary also highlights the disturbing preparations for the so-called “Freak-Offs,” which involved a range of drugs and sexually charged activities. Pines reveals that he was tasked with setting up rooms filled with ketamine, marijuana, male libido supplements, and even baby oil, among other items. In the aftermath, Pines often found himself cleaning up the wreckage—broken glass, stains, and the unpleasant remnants of the wild parties.
“The smell of baby oil is something I’ll never forget,” Pines says, visibly shaken. “It became a trigger for everything that happened—things you can only imagine.”
Legal Battles and Accusations of Sexual Battery
The revelations come amidst an ongoing legal battle, where Pines has filed a lawsuit against Combs, accusing the music mogul of sexual battery, harassment, and sex trafficking. In the suit, Pines describes his time working for Combs as a period of fear and manipulation, where he was treated as little more than a pawn in a twisted game of power.
Pines now labels Combs a “predator” who used his position to control and manipulate his employees for his own pleasure. He recalls witnessing the physical abuse of other employees who dared to challenge Combs’ demands, further underscoring the toxic and dangerous environment at Combs Enterprises.
The Fall of Diddy: A Look at the Bigger Picture
As Combs faces mounting legal troubles—including charges related to sex trafficking and racketeering—The Fall of Diddy documentary provides a deeper look into the darker side of his empire. Pines’ account sheds light on the toxic work culture, the abusive power dynamics, and the manipulation he claims were rampant in Combs’ circle.
The exclusive 30-minute interview with Pines is a pivotal moment in the four-part docuseries, conducted by investigative journalist Mara S. Campo. It marks the first time that Pines has shared his side of the story on camera, offering an intimate and disturbing look into the real cost of loyalty to the once-celebrated mogul.
The Legacy of a Troubling Empire
As the final episode of The Fall of Diddy airs, the series leaves viewers with a sobering reminder of the dark undercurrents that have long plagued the entertainment industry. With Combs now behind bars awaiting trial, the future of his brand and legacy remains uncertain. For Pines and others like him, however, the scars of their experiences are far from over.
The Fall of Diddy is now available for streaming on Max and Discovery+, offering a deeper dive into the chaos that has surrounded one of hip-hop’s most controversial figures.