Diddy’s Assistant Begged Diddy to Take Him Away From His ‘Hater Boss’

Sean Combs, aka Diddy, is well-known for his music and business ventures that launched him to stardom. The artist is so well known that even his assistant, Derek Watkins (whom he renamed Fonzworth Bentley), also attained fame. Here’s what Diddy’s assistant said about the first time they met — and how he texted for the job.

Diddy’s assistant, Derek Watkins aka Fonzworth Bentley, dressed to impress before he ever met Diddy

Diddy and his assistant Derek Watkins aka Fonzworth Bentley in suits at an event
Diddy and Derek Watkins aka Fonzworth Bentley | Jeff Kravitz/FilmMagic, Inc

It took years for Diddy to invite Derek Watkins, aka Fonzworth Bentley, to become his assistant. But Watkins made sure to dress to impress while in New York City, as he never knew when opportunities would arise. Prior to meeting the superstar, he worked at the Ralph Lauren store on Madison Avenue.

“I would always go out dressed,” Watkins told Angela Yee in a 2009 interview about meeting Diddy and becoming his assistant. “The only people dressed in any of the little hip-hop events were the Wall Street guys. This is gray suit, navy suit, white shirt, you know, very boring. So, when I’m in the chocolate brown three-piece, lavender shirt … you know, with the chocolate brown suedes blessing heads, I stood out.”

Watkins then explained he would see Diddy at events, and he’d say a few words and walk off. “It became almost like an inside joke,” Watkins continued.

Derek Watkins begged Diddy to take him away from his ‘hater boss’

Eventually Derek Watkins and Diddy developed a report after seeing each other multiple times at New York events. The entrepreneur gave Watkins his number when they both were at Justin’s, P. Diddy’s soul-food restaurant in Chelsea, The New York Times notes. Watkins told Angela Yee he waited to call.

Finally, Watkins contacted Diddy after working a shift at a restaurant. Diddy responded several times asking who was contacting him. “And now I understand this is the importance of branding,” Watkins continued. “I said, it’s Derek Watkins, the suit master.”

At first, Diddy didn’t reply. Watkins prayed to his father and God to know what to say next. Finally, he leveled with Diddy and essentially asked him for a job right there. “Please don’t make me go back to my hater boss,” Watkins said.

“I remember the day exactly,” Watkins told The New York Times. “It’s going to be in the movie about my life. Sean waved his hands in my face and said, ‘Your life has just changed. Are you ready?'”

What happened to Fonzworth Bentley? Here’s what he’s doing now

Derek Watkins aka Fonzworth Bentley and Diddy posing at a formal event
Fonzworth Bentley and Diddy | Johnny Nunez/WireImage

So, what is Derek Watkins aka Fonzworth Bentley up to today? Nicki Swift notes Diddy’s assistant went on to pen an etiquette book in 2007 and he married actor Faune Chambers in 2010. They have two children together.

Watkins was well-known for his music background, too, and he continued working on music through the years. He assisted Kanye West on two of his notable albums, Yeezus and The Life of Pablo. Watkins created and produced songs for the ABC show black-ish, and he also created choreography for the spinoff show, grown-ish. He also appeared in multiple TV shows and movies over the years, and he seems to still have a good relationship with Diddy today.

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