10 Recent Shocking Details About Diddys Freak Offs

10 Recent Shocking Details About Diddys Freak-Offs

Welcome to WatchMojo, and today were breaking down the darkest, most disturbing details about freak-offs that have emerged in the criminal trial of Sean Diddy Combs.

Combs Favorite Place to Hold Freak-Offs

On the heels of the news that Diddys defense team is reportedly seeking a pardon from President Donald Trump comes another bombshell. David James, a former assistant to Sean Combs, testified that the disgraced moguls preferred location to set his freak-offs was at the Trump International Hotel in New York City. James revealed that the hotel personnel knew him very well, and even gave him a key to the building, as he coordinated the transportation of supplies to the various freak-offs. In a resurfaced 2012 clip from The Celebrity Apprentice, future president Trump said that he loved Combs and referred to him as a good guy.

Cassies Refusal to Participate in a Freak-Off Resulted In That Hotel Footage

If youve been following the turbulent Combs case, then youll likely remember the disturbing security camera footage published by CNN that depicted the rapper violently attacking Cassie Ventura. Ventura, the federal governments key witness in the trial, was Combs on-again, off-again partner for over a decade. As Ventura testified in May of 2025, that 2016 footage was the result of her trying to leave one of the freak-offs. Said Rachel Maimin, a former federal prosecutor for the Southern District of New York, It sets the stage for the rest of the case, where the prosecution is going to have to back up her testimony with all of their evidence.

Combs Had Employees On Payroll to Operate Freak-Offs

While the man formerly known as Puff Daddy is currently the only defendant facing criminal charges, its abundantly clear that he couldnt have gotten away with it all by himself. To that end, the federal indictment against Combs alleges that he used the Combs Business, including certain employees, to carry out, facilitate, and cover up his abuse and commercial sex, and that [t]hose employees including security staff, household staff, personal assistants, and high-ranking supervisors and other close associates acted as Combs intermediaries. Those employees were responsible for, among other responsibilities, procuring baby oil, as well as booking and cleaning hotel rooms. In addition, they were expected to deliver both commercial sex workers and large amounts of cash to pay them with.

Meet The Punisher

Just so its clear: were not talking about Frank Castle. No, in this case, the Punisher is the stage name of exotic dancer Sharay Hayes, whose testimony revealed several bizarre, previously unknown aspects of the freak-offs. Said the BBC, Hayes was hired to create sexy, erotic scenes with Combs' then-girlfriend [Cassie] while a naked man watched from the corner. Perhaps strangest of all was the conditions under which Hayes was expected to work: not only was he instructed to completely ignore the aforementioned naked man, but Diddy wore a veil to cover his face. Hayes testified that, over eight to 12 encounters with the two, Combs watched and gave directions. The directions included adjusting candles and instructing the two to have sex.

Meet Jonathan Oddi

The South African-born Oddi first rose to notoriety in 2018 after storming the Trump National Doral Miami and engaging in a firefight and chase with police. A particularly confusing detail was Oddis reported references to Diddy at the time which were explained somewhat by the ongoing trial. Cassie Ventura identified him as one of the escorts that Combs had hired for the freak-offs, and that his 2018 claims of being a sex slave actually bore some merit. Oddi elaborated in a Miami Herald interview from prison, stating that hed sometimes been requested to wear a police officer uniform, and that he made $800 per quote-unquote performance.

How Combs Guaranteed Freak-Off Participation

During her often disturbing testimony, Cassie frequently spoke of the ways that Combs would attempt to control her and ensure her submission. In one such case, Diddy allegedly forced her to carry one of his many firearms she has retroactively described it as a scare tactic. Not unlike what he did with Cassie, Combs is described in the indictment as using his considerable power and influence to rope unwilling victims into participating. As the document describes, these methods included obtaining and distributing narcotics to them, controlling their careers, leveraging his financial support and threatening to cut off the same, and using intimidation and violence.

Combs Prepped a Freak-Off While Waiting to Be Arrested

The moguls long career in music came to a decisive end following his September 2024 arrest at the Park Hyatt Hotel in Midtown Manhattan. You might have heard that part the part you might not have known about would be the fact that, despite the knowledge that he would have to surrender to authorities, he was undergoing prep to hold yet another freak-off. The publicly released images of Combs hotel room were what gave rise to the now-infamous baby oil memes, and a grim insight into how he worked and operated. According to Special Agent Yasin Binda, some of the mysterious powders and substances found in the room were determined to be the narcotics ketamine and MDMA.

Combs Carefully Planned Out the Freak-Offs

Like a supervillain orchestrating his master plan, Diddy was tightly in control of all aspects of the freak-offs. And we mean all aspects: per Cassies testimony and as described by the New York Times, Assistants and security guards would stock the room with condoms, baby oil and Astroglide, a lubricant. Cassie also testified that Combs asked that the baby oil be heated and that he wanted her glistening with it, requiring that she apply it in frequent intervals. Ventura even went so far as to describe the freak-offs as very choreographed, and explicitly tailored to realize his voyeuristic personal fantasies.

Combs (& His Participants) Needed IV Replenishment Afterwards

The freak-offs have been reported to last for days at a time, becoming a physically and emotionally exhausting experience for those strong-armed into participating. Part of Combs employees responsibilities, as noted in the federal indictment, was securing large quantities of IV fluids to help with his recovery afterwards. Cassie testified that, alongside the IV fluids, Combs would provide massages and professionally cooked meals. Even those supposed kindnesses came with a dark side: given the frequency of the freak-offs, Cassie noted that her reliance on the fluids left her with an opioid addiction.

The Freak-Offs Were Filmed & Combs Held On To the Footage

Perhaps most disturbingly of all, its now public knowledge that Diddy conspired to have the freak-offs filmed, and used as blackmail and extortion material. In one hard-to-stomach incident, Cassie recalled Combs playing a video of a sexual encounter in public. In a 2013 recording played by Diddys lawyers, Cassie is heard threatening a man who claims to have such footage. David James, Diddys ex-assistant, also testified that Combs claimed to have kept a video of James dancing while on drugs, implying that he would hold on to it in case I ever need it.

Which freak-off revelation shocked you the most? Be sure to let us know in the comments!