The explosive docuseries ‘The Fall of Diddy’ is reaching its final chapter, and with it comes a chilling revelation from Sean ‘Diddy’ Combs’ former assistant, Phillip Pines. Breaking his silence, Pines details the disturbing experiences he endured while working for the disgraced music mogul, including shocking claims of coercion, abuse, and the twisted “loyalty tests” he was allegedly forced to pass.
In the documentary’s final installment, Pines shares a tearful testimony about what really went on behind closed doors at Diddy’s alleged notorious gatherings—events insiders have referred to as “Freak-Offs.” According to Pines, these wild parties were fueled by drugs, alcohol, and an anything-goes atmosphere where power dynamics were manipulated for Diddy’s own entertainment.
Pines claims that during one such night, his former boss, intoxicated and caught up in the party chaos, demanded that he prove his “loyalty.” Referring to himself as a “king,” Diddy allegedly ordered Pines to engage in a sexual act with a woman at the gathering. The former assistant describes the terrifying moment when he was handed a condom and pushed toward an unsuspecting guest. Feeling trapped, he complied briefly before seizing an opportunity to escape when Diddy looked away
According to Pines, these disturbing encounters were not isolated incidents. He alleges that as part of his job, he was also tasked with setting up private rooms in hotels or Diddy’s lavish estates for what was internally known as “Wild King Nights.” These events reportedly required meticulous preparation, with a “laundry list” of items including ketamine, marijuana, baby oil, hallucinogenic mushrooms, male libido enhancers, and the lubricant Astroglide.
Beyond preparation, Pines describes the grim aftermath of these nights—detailing how he was often responsible for “emergency cleanup” operations. The scenes he encountered were nothing short of horrifying: stained furniture, shattered glass and pools of baby oil covering floors, creating a slick and hazardous environment. The act of scrubbing away the evidence of these events became one of the most mentally and emotionally draining aspects of his job.
Pines, who worked for Diddy between 2019 and 2021, has since filed a lawsuit accusing his former employer of sexual battery, harassment and trafficking. He describes his time working for the rapper as deeply traumatic, stating, “My life changed and I’ve never really recovered from it.”
One of his greatest fears, Pines reveals, was speaking out. He had allegedly witnessed firsthand how Diddy handled those who disobeyed him recalling instances where the music mogul physically assaulted employees who refused to comply with his demands. This climate of fear kept Pines silent for years.
Diddy, once a towering figure in the music industry, is currently behind bars, facing multiple charges, including sex trafficking and racketeering. The accusations continue to pile up as more individuals step forward with accounts of his alleged abuses.
‘The Fall of Diddy’ docuseries finale, featuring the bombshell testimony of Phillip Pines, is set to air on Investigation Discovery (ID) on January 28 at 9 p.m. ET. Viewers can also stream it later on Max and Discovery+. Additionally, a special 30-minute interview with Pines, conducted by journalist Mara S. Campo, will offer an even deeper look into his harrowing experiences. This will be the first time he speaks openly on camera about the alleged horrors he endured while working for Combs.
