Remember Fonzworth Bentley? Here's what happened after he moved on from holding umbrellas for Sean ‘Diddy' Combs

CNN

4 hours ago

Before there were influencers, Fonzworth Bentley became famous for being adjacent to the influential — namely Sean 'Diddy' Combs.
Whether he was the umbrella-holder-in-chief or making appearances on Combs' various television projects, as Combs' personal assistant, Bentley was in the orbit of new millennium cool of the early aughts.
For the personal assistants who followed Bentley, we now know more about what working for Combs entailed for them.
In recent weeks, the jury in Combs' federal criminal trial has heard from five former employees of Combs' who served as his assistant for all or some of their time working with him. Through their testimony, which in some cases was delivered under immunity agreements, prosecutors aim to prove Combs' used his businesses and staff in service of a criminal enterprise in which the government claims Combs engaged in sex trafficking, forced labor, kidnapping, arson, bribery and obstruction of justice between 2008 and 2024.
Combs has pleaded not guilty to charges of racketeering conspiracy, sex trafficking and transportation to engage in prostitution.
Derek Watkins, Bentley's given name, stopped working for Combs in 2004, four years prior to any allegations in the federal case. He has not been named in any civil litigation or the criminal case against Combs. But his role in Combs' life has not gone unmentioned by trial observers who have made a sport of dissecting Combs' old media appearances in search of clues that might answer the questions playing out in court: What exactly did Diddy do?
During a 2004 late-night TV conversation with Conan O'Brien, Combs raved about Watkins, a dapper gentleman who was famously once photographed holding an umbrella for Combs to shield him from the St. Tropaz sun. At the time of the interview, Watkins was no longer employed by the music mogul.
'He's an entrepreneur,' Combs said of Watkins. 'He's moved on to bigger and better things.'
But it was what Combs said later in the conversation that has some people wishing Watkins would say more about his time working for Combs.
O'Brien asked the music mogul about his practice of sending someone from his staff to hotels ahead of his stays to prepare his room.
'It's called 'preparing the sexy,'' Combs explained. 'I definitely take pride in being the originator of the preparation of the sexy.'
Combs said that entailed having candles, flowers and a specific scent in his rooms.
Prosecutors have painted a different picture about alleged incidents years later.
Details around so-called 'Freak-Offs' and 'hotel nights' between 2008 and 2024 have been central to the prosecution's case against Combs in testimony from his former assistants, the alleged victims and male entertainers paid to participate in some of the alleged drug-fueled sexual encounters.
The first time Combs' former executive assistant George Kaplan was tasked with setting up a hotel room for Combs, he was given a bag and told to unpack it, he testified last month. The bag had clothes, a speaker, candles, liquor, baby oil and Astroglide, said Kaplan, who testified under an immunity order. After that first time, he said he would often buy the same supplies with his corporate credit card.
Kaplan testified that after Combs would leave a hotel room, he'd go in and pack up Combs' belongings and tidy up. On one occasion, he cleaned up a 'brown crystallized powder' off a countertop, though he said he didn't know what it was.
Asked why he didn't let the hotel staff clean up, Kaplan said he came to understand part of his role was protecting Combs' image.
'Protecting him and protecting his public image was very important and that was something I was very keen on doing,' he said.
Watkins has not spoken publicly about the allegations against Combs.
CNN reached out to Watkins and his former representatives for comment.
Watkins, like others once close to Combs, has seemingly moved on.
Watkins married and had kids. His infrequent social media presence is a collection of tributes to other entertainment artists, sponsored posts from brands like Lego and the occasional inspirational message.
'How your life feels is much more important than how it looks,' an Instagram post from Watkins, shared last year, reads.
Of course, Watkins' time in Combs' circle was, at least then, very important to him.
It was Watkins' distinct style - tailored three-piece suits and colorful ties - that sparked his introduction to Combs. During a 'Shade 45 Morning Show' conversation in 2009, Watkins recalled bumping into Combs at events around 2001 in New York City, where Watkins had moved from Atlanta and was then working at Ralph Lauren's flagship store.
The two would talk fashion and those interactions led to them exchanging numbers. Watkins decided to appeal to the entrepreneur's shared sense of ambition, he said. (Combs had clawed his way up himself by leaving Howard University to intern for Uptown Records).
'I just picked up the pager (and wrote), 'You remember that guy that traveled from Howard University to intern with (Uptown Records head) Andre Harrell? I'm that guy in 2001,'' Watkins told the radio show's host Angela Yee.
Combs told him to come to work and sent him an address, according to Watkins.
'I literally started training that day as his assistant,' he added. 'The rest is history.'
There may not be anyone more visibly linked to Combs at the height of his success and the tabloid culture of the early 2000s than Watkins. 'Fonzworth Bentley' was a nickname from Combs and one of his associates that became a public persona, as Watkins was photographed with Combs at events and appeared on the MTV reality show 'Making the Band 2.'
He was also deridingly compared in some press to a 'manservant,' a term Watkins disliked.
Critics of their professional dynamic believed seeing Watkins 'subservient' to the mogul was a painful reminder of a time when those types of positions were all that were available to African Americans.
In a 2004 interview with the New York Times, Watkins brushed off the criticism as handedly as he would lint on a lapel.
'A pioneer always looks crazy until he finds dry land,' he told the publication.
'He was never a manservant. He had a very respectable job, and when he held up an umbrella for me, that was his idea, because it's entertainment,' Combs said in a 2017 interview. 'And he knows I don't like to get hot.'
Watkins' post-assistant projects included hosting MTV's 'From G's to Gents,' a makeover series for aspiring gentlemen. He appeared in rap duo OutKast's 'The Way You Move' and 'Roses' music videos and had a small role in the 2006 film 'Idlewild.'
Watkins also had parts in the movies 'Honey' and 'Fat Albert.' He launched a line of high-end umbrellas and authored the etiquette book, 'Advance Your Swagger: How to Use Manners, Confidence and Style to Get Ahead.'
His former boss helped influence him getting into the music industry. Watkins rapped on Da Band's 2002 album 'Too Hot for TV' and in a skit on Outkast's famed album 'Speakerboxxx/The Love Below.'
He released his debut album 'C.O.L.O.U.R.S' in 2011, but it was Kanye West who gave him the most visibility in the music industry.
West featured Watkins on his album 'The College Dropout' and gave him a songwriting credit on the 2013 album 'Yeezus.' He has continued contributing to creative projects in the entertainment industry, more recently on shows like 'Black-ish.'
In a 2022 interview with Forbes, Watkins described how he works with fellow artists.
'It's really about listening and being aware, and being present, but also being able to understand that artist and understand their fears and insecurities,' Watkins said. 'It's also about being able to see something in them that they may not see in themselves that I help unearth.'
He also reflected on his time working for Combs two decades prior.
'How Sean Combs runs his life is like a consigliere,' Watkins said. 'He really does live like the 'Godfather, Part II.''
CNN's Eric Levenson, Lauren del Valle, Nicki Brown and Kara Scannell contributed to this report.