Diddy’s ex-assistant makes shocking allegations about what he was ordered to do to ‘prove’ his ‘loyalty’

A man who alleges to be an ex-assistant of Diddy's has made some bombshell allegations about the rapper.

Diddy is currently being held at Metropolitan Detention Center in Brooklyn, New York, and will remain behind bars until his trial on May 5.

The rapper has been charged with sex trafficking, racketeering conspiracy and transportation to engage in prostitution, and will land himself a life sentence if found guilty of racketeering.

Meanwhile, he faces a statutory minimum of 15 years for the sex trafficking charge, and up to ten years for transportation to engage in prostitution - he's pleaded not guilty to all charges.

As well as facing criminal charges brought forward by the state, Diddy has been slapped with a series of civil suits.

Diddy is currently being held in a New York prison until his trial (Dave Benett/Getty Images for TAO Group Hospitality)

One woman has alleged that she was drugged and raped by the Grammy Award-winning hip-hop star, an encounter that lead to her falling pregnant.

In December 2024, lawyer Tony Buzbee, who is representing many of Diddy's alleged victims, said that the rapper could ultimately face as many as 300 civil suits, BBC News reports.

Another person who has filed a civil suit against Diddy is his former assistant Phillip Pines, who says he worked for the 'I'll Be Missing You' singer from 2019 through to 2021.

According to PEOPLE, Pines is suing Diddy for sexual battery, sex trafficking and intentional infliction of emotional distress as well as other accusations.

In a lawsuit seen by Variety last year, he alleged that he was the rapper's 'personal lackey' and was often assigned to cleaning up where 'Wild King Nights', which he claims were events where Diddy would engage in sex, drugs and alcohol with 'female guests or other guests'.

In a new HBO documentary titled The Fall of Diddy, Pines was interviewed, and in the tell-all chat, he shared a series of accusations about his time working for Diddy.

The disgraced rapper has denied all the allegations he's facing (MEGA/GC Images)

Discussing one of Diddy's infamous 'freak offs', Pines claimed he was encouraged to participated in X-rated antics and to take shots of alcohol.

"That was his way of making sure you felt comfortable," he said of the alleged booze drinking (via New York Post).

"I go back to the office, sit there, get summoned again, take a shot, take a shot. He’s out of his mind. He’s in rare form as we would call it."

Sharing what he allegedly had to do to prove his 'loyalty' to his then-employer, Pines claimed: "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?

"I didn’t know what to do."

He says the woman gave Pines her consent to have sex with her and he 'performed for a little' before running out of the room.

In his lawsuit, Pines also made reference to this alleged event, as well as claiming he was asked to show his 'loyalty' in other ways, like coming to his home just to give him his remote.

As well as the criminal charges he's facing, Diddy has denied all the allegations he's facing that have been detailed in the civil suits that have been filed against him.

Diddy is one of the biggest names in hip-hop (Samir Hussein/Getty Images for Sean Diddy Combs)

An attorney for the music star told The New York Post: "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."

UNILAD has contacted Diddy's reps for further comment.

If you've been affected by any of the issues in this article, you can contact The National Sexual Assault Hotline on 800.656.HOPE (4673), available 24/7. Or you can chat online via online.rainn.org.