The controversial legacy of Sean ‘Diddy’ Combs. Here’s what we know
Sean ‘Diddy’ Combs faces federal sex crime charges. Here’s what we know about his controversial legacy.
NEW YORK – Screams erupted from Fifth Avenue: Sean “Diddy” Combs had arrived.
At around 8 p.m. on the first Monday in May, Diddy ascended the famed steps of the Met Gala red carpet, draped in a black puffer cape atop a black motorcycle suit jacket embroidered with black pearls. The custom Sean Jean cape, adorned with black camellias, was a nod to fellow controversial fashion figure Karl Lagerfeld, to whom the year’s event paid tribute.
He was arm-in-arm with then-girlfriend Yung Miami, excitedly saying “What’s up, yo?” to journalists at the top of the cream-colored carpet before heading inside the festivities, which celebrate and fund the Metropolitan Museum of Art’s Costume Institute and annual exhibit. The two exited fashion’s biggest night early as they prepared to host an afterparty.
This was in 2023, the same year he received lifetime achievement honors and the key to New York City. It’s also when his world – one defined by success and excess – began to crumble.
On Met Gala Monday, May 5, Combs will be five miles away from the glamorous festivities in a downtown Manhattan courtroom, where jury selection will begin on the first day of his sex-crimes trial. Instead of posing on the Met steps, as in years past, he’ll be transported from a jail cell at Brooklyn’s Metropolitan Detention Center to face five counts on charges of sex trafficking, racketeering and transportation to engage in prostitution.
It’s a stunning downfall for power player Combs, 55, who spent years surrounded by his entertainment and fashion industry peers, now reduced to being evaluated by a jury of his peers instead.
The trial’s timing with one of the most exclusive events in his hometown of New York City is jarring – especially considering 2025’s theme and dress code.
Diddy as a dandy: The 2025 Met Gala theme
Combs – also known by the monikers Puff Daddy, Puffy, P. Diddy and Diddy – regularly attended the annual event, benefiting the Met’s Costume Institute with a lavish fundraising gala that has only increased in scale over the years.
Combs’ rise alongside the Met Gala directly relates to the 2025 theme highlighting “the importance of style to the formation of Black identities.” With the Superfine: Tailoring Black Style exhibit, the “Black dandy” and the importance of Black styling to the cultural zeitgeist is on full display.
The rapper, producer and record executive’s Sean John clothing brand brought him international acclaim and industry accolades, and he was the first Black man to win a Council of Fashion Designers of America Award in 2004. “Who’s the original luxury street brand?” Combs asked Vogue in 2023. “It’s Sean John.”
Combs’ place in the fashion realm only grew as he continued elevating his ensembles, often switching between luxe street style with his own logo and impeccably tailored suiting, even touting his own umbrella-holding butler, stylist and certified aughts dandy Fonzworth Bentley. (“He had a very respectable job, and when he held up an umbrella for me, that was his idea, because it’s entertainment,” Combs once told New York Times Magazine of Bentley.)
At its core, the Black dandy figure prioritizes fashion and aesthetics to engage in power dynamics through personal style. This year’s Met Gala, and its “Tailored for You” dress code, would likely have been Diddy’s playground.
It’s not difficult to envision him as one of the co-chairs for the evening, helping to set the tone and curate one of the biggest nights in fashion and entertainment for the top-tier A-listers on the invite list. With co-chairs this year including rapper A$AP Rocky, actor Colman Domingo, race car driver Lewis Hamilton, producer and designer Pharrell – and honorary co-chair LeBron James – Combs before the fall might have tailored his presence to fit just so.
Now, Diddy’s courtroom fashion – a judge-approved mix of shirts, sweaters, slacks and laceless shoes – will be what onlookers assess as prosecutors charge that Combs ran a “criminal enterprise” in which he and associates engaged in kidnapping, arson, physical violence and sex trafficking.
Diddy’s Met Gala appearances with Cassie viewed through new lens
Diddy and ex-girlfriend Casandra “Cassie” Ventura Fine attended multiple Met Galas together in the years of their relationship. That was before her bombshell civil suit against Combs in November 2023, in which she alleged rape, physical abuse and sex trafficking at the hands of the music mogul.
Though the suit was quickly settled the day after it was filed, it’s been seen as the catalyst for dozens of other civil suits filed against Combs also alleging three decades of abuse and sexual misconduct.
Combs and Cassie began dating in 2007 and had an on-and-off relationship for more than a decade. In 2005, 19-year-old Cassie met Combs, then 37, when he expressed interest in signing her to his Bad Boy Records label.
What looked like a romantic relationship to the outside world is now being viewed from a new vantage point – including their multiple trips to the Met Ball.
They were arm in arm at the exclusive event in 2015 for China: Through the Looking Glass, 2017 for Rei Kawakubo/Comme des Garçons: Art of the In-Between and 2018 for Heavenly Bodies: Fashion and the Catholic Imagination, their last before splitting later that year. Cassie claimed in her lawsuit that Combs raped her in September 2018.
Their appearance at the 2015 fête, captured in a Vogue interview video clip with late Vogue creative director André Leon Talley, is notorious among Diddy trial onlookers. Internet sleuths have latched onto Diddy’s perceived demeanor when Talley greets Cassie first, with a flicker of anger in Combs’ eyes as he pulls her closer to him.
In 2018 for the Heavenly Bodies theme, he told The Hollywood Reporter: “This is how we would be dressed when we arrive at heaven’s gate.” Flanked by Cassie at the top of the Met steps, he later told Vogue on the red carpet, “I just wanted to keep it simple and plain. Angelic.” In perhaps a prescient moment, red carpet correspondent Liza Koshy asked Cassie if she had anything to confess; Combs stared intently. “I keep everything right here,” Cassie says as she lifts her hands to her heart in prayer, before quickly pointing to Diddy, “Or right here.”
Diddy’s final Met Gala appearance was that fateful day in 2023. He’s now graying, in a tan prison uniform and far from his kingdom at the top of the Met staircase. Where the first Monday in May will take him is anybody’s guess.
Contributing: Jay Stahl and Taijuan Moorman
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