Long before he was accused of sexual misconduct in a series of lawsuits, and long before federal agents in military gear raided his homes in Miami and Los Angeles, Sean Combs was unforgivable.
That was the name he had selected for his first fragrance, which he sold through a partnership with Estée Lauder.
It was promoted as a scent that “exudes the energy, sexiness and elegance of Sean Combs,” and he was supposed to give it a publicity boost in April 2006 by ringing the opening bell of the New York Stock Exchange alongside William Lauder, the Estée Lauder chief executive, and Terry Lundgren, the head of Federated Department Stores.
But Mr. Combs didn’t arrive in time for the opening of the market, saying he had been stuck in traffic. So his fellow business titans did the honors without him.
By then, Mr. Combs had successfully made the transition from Puff Daddy to the world’s most successful hip-hop mogul.
As the founder and chief executive officer of the thriving Bad Boy Entertainment, he made himself into a Jay Gatsby for the hip-hop generation, complete with “White Parties” in the Hamptons.
Vanity Fair noted his platinum sales, his Grammys, his fashion line, his turn on Broadway in “A Raisin in the Sun” and his “Vote or Die” get-out-the-vote campaign, adding that he “has had his hands in almost every thinkable aspect of popular culture and left his mark on each.”
Mr. Combs, 54, was someone who realized, before almost anyone else, that music could serve as the foundation of the mansion he was building for himself.
“He really did set the template for a certain kind of hip-hop entrepreneurism,” said Michael Hirschorn, the founder and chief executive of Ish Entertainment, a New York production company, and the former head of programming at VH1. “He was really the first guy, along with Russell Simmons, who understood the value of taking your name and putting it on literally everything.”
And yet some former colleagues and business associates said in interviews for this article that they found it hard to read the recent coverage of Mr. Combs without seeing his apparently sudden downfall as part of a slow decline.
The very qualities that enabled him to see across different landscapes might have been his Achilles’ heel, said Teri Agins, a former Wall Street Journal reporter and the author of “Hijacking the Runway: How Celebrities Are Stealing the Spotlight from Fashion Designers.” Mr. Combs bounced from one branding opportunity to another as he “checked off boxes,” Ms. Agins said, without seeming to realize that the real measure of a business mogul comes not with the ignition of liftoff but with the ability to maintain a mile-high altitude.
He grew up in Mount Vernon, N.Y., and was raised by his mother, Janice Combs. He attended Mount Saint Michael Academy, a Roman Catholic high school in the Bronx, and went on to major in business at Howard University. Things moved quickly after that. As an intern at Uptown Records, a label founded by Andre Harrell, he helped produce hit remixes and “Real Love” by Mary J. Blige, a song that introduced the rapper the Notorious B.I.G.
Mr. Combs wasn’t cut out for the life of an employee, and he started Bad Boy in 1992. It was a time when the hard polemics of Public Enemy and the earthy ethos of De La Soul and A Tribe Called Quest gave way to a culture of flash, with Mr. Combs as its avatar.
In 1998, he branched out into fashion with his men’s wear label, Sean John.
“He knew that, when your name also signals a lifestyle, he could market that in many ways and forms,” said Samantha N. Sheppard, an associate professor and chair of the department of performing and media arts at Cornell University.
He was photographed by Annie Leibovitz for a 1999 Vogue feature headlined “Puffy Takes Paris,” in which he is seen in the company of the model Kate Moss and the industry heavyweights Oscar de la Renta, John Galliano, Jean Paul Gaultier and Karl Lagerfeld. “It became all about rap culture and high fashion and the meeting of the two worlds,” Ms. Leibovitz said of the shoot in a later interview.
In December of that year, he arrived, dressed in white, with his then-girlfriend, Jennifer Lopez, at the annual Met Gala. He performed during the dinner and chatted with Henry Kissinger, who was heard asking the socialite Pat Buckley, “Why does he call himself Fluffy?” Lil’ Kim was also present, signaling that a party once reserved for New York’s old aristocracy was changing with the times, a shift ushered in to a great extent by Mr. Combs.
A few weeks later, he and Ms. Lopez made tabloid front pages after they fled a nightclub where shots were fired, leaving three people injured. Mr. Combs was arrested, but later acquitted; his latest hip-hop protégé, Jamal “Shyne” Barrow, was convicted and sentenced to 10 years in prison.
In 2002, Mr. Combs beat another world-famous tabloid showman to the punch of reality TV as the host of “Making the Band,” MTV’s precursor to “The Apprentice.” The show is probably best remembered for Mr. Combs’s demand that the contestants walk the five miles on foot from Midtown Manhattan to Junior’s in Brooklyn to fetch him a slice of cheesecake. When his charges protested, he told them they would be dismissed if they failed the mission.
In 2001, he offered a live broadcast of a Sean John fashion show on E!, making the runway more accessible to a wide audience. Two years later, the Yucaipa Companies, a private equity fund operated by the California billionaire Ron Burkle, poured a reported $100 million into Mr. Combs’s clothing label. The next year, the first Sean John store opened on Fifth Avenue, across from the New York Public Library.
Maxwell Osborne, the head of the fashion brand An Only Child, started his career as an intern at Sean John at around that time. In an interview, he said he had no doubt that there were people who had “horrible” experiences working for Mr. Combs. Yet he was not among them.
He recalled Mr. Combs as someone who saw no hierarchies, who considered Mr. Osborne a member of the design team from the beginning. Mr. Combs nicknamed Mr. Osborne “One Dread” and invited him to his parties in the Hamptons.
“He saw tension as part of how you make diamonds,” Mr. Osborne said, adding that Mr. Combs didn’t hold it against employees who pushed back on him.
In 2004, Diddy was named the year’s best men’s wear designer at the Council of Fashion Designers of America’s annual awards ceremony, beating out Ralph Lauren and Michael Kors. He was the first Black person to win the honor. In his acceptance speech, he gave a shout-out to Mr. Lauren and announced: “I am living the American dream.”
He used his newfound status and understanding of power-sharing to invest in other brands, including that of Zac Posen, then an up-and-coming designer favored by the Vogue editor Anna Wintour. In those days Mr. Combs was often seated in the front row of Mr. Posen’s shows, next to Ms. Wintour, as the models traipsed by. And he hosted high-octane fashion shows of his own at Cipriani in Manhattan.
He also appeared then in the successful 2004 revival of Lorraine Hansberry’s “A Raisin in the Sun” that, according to the theater publicist Rick Miramontez, set a new template for how to market a play.
Rather than trying to reel in white tourists, the producers courted a Black audience with a campaign that included ads on urban radio. The influence on producers was “seismic,” Mr. Miramontez said, and the strategy was later used in hits like “Slave Play.”
“He knew how to launch both people and products,” Ms. Sheppard, the Cornell professor, said. “Diddy really knew and knows how to market Black cool — the idea that fashion, specifically streetwear, could aesthetically signal a kind of cultural relevance and cultural capital, to both Black people and wider and whiter audiences.”
In 2006, the New York Post reported that Unforgivable was bringing in $1.5 million in sales per week. That was more than new fragrances from Calvin Klein, Vera Wang and Juicy Couture, according to the NPD Group, a market research firm, which reported that Mr. Combs’s cologne outsold every other new fragrance that year.
Mr. Combs announced his sequel cologne, “I Am King,” in 2008 with a Times Square advertisement — showing him in a white tux — that was reported to be the tallest billboard in Manhattan up to that point. But “I Am King” didn’t match the sales of his original scent, former colleagues said. And Mr. Combs’ habit of showing up hours late to meetings and berating Estée Lauder executives became a source of consternation, said one person who was granted anonymity to describe internal business meetings.
In 2009, Estée Lauder opted not to renew Mr. Combs’s contract. That was when things seemed to take a turn.
Mr. Combs’ venture into women’s wear did not meet with the success of his men’s line. He “got blinded by the headlights of superstardom,” said Jeffrey Banks, a CFDA board member who worked for Ralph Lauren and Calvin Klein before starting his own brand in the 1970s.
Restless and ambitious, Mr. Combs explored the idea of starting a cable network with Mr. Burkle and Bob and Harvey Weinstein. “For a minute, I was going to be the fifth partner on it,” Mr. Hirschorn said. “Then the whole thing kind of collapsed for reasons that weren’t super clear. But I think he imagined, ‘I’m going to take over the means of production and not only be a star.’”
By then, the Sean John label had crested. Mr. Combs obtained what industry colleagues said was a lucrative deal as a spokesman for Diageo, the alcoholic beverage company behind Johnnie Walker, Tanqueray, Guinness and other brands — only to be outdone in that field by a fellow celebrity turned business mogul, George Clooney, who started a tequila brand with two partners and ended up selling it to Diageo for roughly $1 billion.
As Mr. Combs’s interests splintered, his fellow hip-hop impresarios caught up. Among other business pursuits, Jay-Z had Rocawear, a clothing line he named after the management company he headed and whose roster included Rihanna and J. Cole. Kanye West achieved scale on his fashion brand largely through a partnership with Adidas. That provided Mr. West with an infrastructure that Mr. Combs lacked, according to Ms. Agins.
Pharrell Williams, the super producer who had worked with Justin Timberlake and Gwen Stefani, moved into fashion with a store called the Billionaire Boys Club. And with the music executive Jimmy Iovine, Dr. Dre started Beats Electronics, a company that would be sold to Apple for $3 billion. Even the famously laid-back Snoop Dogg found himself in The Wall Street Journal.
Ultimately, Ms. Sheppard said, Mr. Combs “was able to see the connection from artistry to industry and aesthetics, but he was also limited by his artistry, which never quite developed enough to get him to the next level.”
In 2013, Mr. Combs finally started his own cable network, Revolt, a would-be competitor to MTV and BET, in partnership with Comcast. At the time of its launch, he opened up about his father, Melvin Earl Combs, in a video titled “Confessions” that was posted on Revolt’s social media channels: “My father was killed when I was 3 years old,” Mr. Combs said, adding, “He was a drug dealer. He was a hustler.”
Mr. Hirschorn said that Mr. Combs “almost pulled it off” when he went into the TV business. “He was right about figuring out a niche low-cost cable channel,” he said. “He was wrong about the decline of cable in general, and it never really did anything that became part of the cultural conversation.”
In 2016, Mr. Combs led a nationwide Bad Boy reunion tour. Lil’ Kim and Faith Evans were among the artists who performed with him. Four New York-area shows sold out, but dates in the Midwest and the South were canceled. Organizers blamed “scheduling conflicts,” while industry people whispered of low ticket sales.
That same year, he sold Sean John to Global Brands Group for an undisclosed sum — only to buy it back five years later for $7.5 million, a seeming reflection of its diminished standing.
Even as he seemed to be settling into the role of elder statesman — a lifetime achievement honor at the BET Awards in 2022; a Global Icon Award at the MTV Video Music Awards in 2023 — Mr. Combs made an attempt to recapture the zeitgeist.
He teased a Sean John couture collection at the Met Gala, when he arrived in a black cape of his own design festooned with camellias. Afterward, he hosted a party at Box, a downtown burlesque club. Guests included Paris Hilton, Marc Jacobs and Ms. Blige.
Later that month, Mr. Combs filed a lawsuit against Diageo in New York State Supreme Court, alleging that he had been subjected to racist treatment by the company. The suit was ultimately settled, without admission of fault on the part of Diageo. Whoever was in the right, what seemed not to be in dispute was that, like many of Mr. Combs’s ventures, his association with the spirits company had fizzled.
In the fall of 2023, Mr. Combs released his first solo album since 2006, “The Love Album: Off the Grid.” Weeks after it was nominated for a Grammy, the singer Cassie, a onetime Bad Boy artist, filed suit against Mr. Combs, accusing him of rape and repeated physical abuse over about a decade.
It was the first in a series of lawsuits filed against Mr. Combs. It is unclear whether they are related to the investigation into his affairs by federal prosecutors in the Southern District of New York and by federal agents with Homeland Security Investigations. Through a lawyer, Mr. Combs has vehemently denied all the claims made against him.
The most recent lawsuit was filed by Rodney Jones Jr., a music producer known as Lil Rod. He accused Mr. Combs of making unwanted sexual contact and of forcing him to hire prostitutes and participate in sex acts during the making of “The Love Album.”
If Mr. Combs thought that, after his more than two-decade foray into various businesses, he would find a safe haven in music, he was mistaken. It seemed that he had gone from “I Am King” to cautionary tale.
Alain Delaquérière contributed research.
