On Monday, federal agents and police raided Sean “Diddy” Combs’ lavish Los Angeles and Miami homes, the latest development in an ongoing investigation of the rapper and music producer. Diddy, 54, is considered to be one of the most influential figures in American music history, which is why all eyes have been on the five lawsuits filed against him in the last four months, alleging physical abuse, sexual violence, and sex trafficking.
The accusations against the music mogul (and other celebrities) span nearly his entire career, going back to the 1990s. Two of the five lawsuits include allegations that Diddy raped the plaintiffs in the early ’90s when he was with Uptown Records. Through his lawyer, Diddy has denied the allegations.
Diddy has been in the business since 1990, when he started as an intern at New York’s Uptown Records before founding his own record label, Bad Boy Records. But while Diddy is undoubtedly most recognized and acclaimed for his music career (he’s credited with discovering musical greats including the Notorious B.I.G, Mary J. Blige, and Usher), music is far from the only, or even the major, contributor to his wealth. He has several business ventures and properties that add up to an estimated $1 billion net worth, as Forbes reported in 2022. Of course, Diddy stands to lose a chunk of change if any of the lawsuits proceed.
Diddy has long been considered one of the wealthiest rappers of all time. In fact, Fortune named Diddy as one of America’s Richest 40 Under 40 in 2002 when he was the founder and CEO of Bad Boy Entertainment and was worth $293.7 million.
So where exactly did Diddy’s fortune come from? It’s a combination of his record deals, properties, a clothing brand, alcohol brand partnerships, acting—and even cannabis.
Music and record labels
During his music career, Diddy released five studio albums, two collaborative albums, one remix album and 72 singles. Diddy’s record label brought in about $130 million annually in its prime, according to a Business Insider report.
His own music—including albums and singles—generates $100 million in royalties, according to fashion and lifestyle magazine Highsnobiety. His first rap album, No Way Out, reached number one on the Billboard 200 in its first week of release, selling 561,000 copies, and received five Grammy Award nominations in 1998. Diddy won the Grammy Award for Best Rap Album that year, and by September 2000 No Way Out was certified as a septuple-platinum album by the Recording Industry Association of America for sales of over 7 million copies.
His subsequent albums also met with success. Throughout his musical career, he partnered with other famous artists including Rick Ross, DJ Khaled, Fat Joe, Busta Rhymes, Red Café, and Fabolous.
Clothing, alcohol, and cannabis
Around the time Diddy’s first rap album came out, he also launched his own clothing brand, Sean John. In 1998, the brand made its debut at Bloomingdale’s in New York City. Sean John’s annual revenues now exceed $525 million, according to Macy’s.
In 2004, Sean John invested in high-end label Zac Posen, and in 2008 acquired streetwear brand Enyce from Liz Claiborne for $20 million. Two years later, Sean John landed a distribution agreement with Macy’s, making the department store the sole distributor of its sportswear.
In 2016, Diddy sold a 90% stake in Sean John to Global Brands Group, but bought it back in 2021 for $7.5 million.
Meanwhile, Diddy also had several alcohol- and cannabis-related investments and partnerships. In 2007, Diddy and alcoholic beverage company Diageo formed a partnership with a goal to increase exposure and sales for Cîroc vodka and DeLeón tequila’s exposure and sales. At the time, the agreement included a 50/50 split with the company, but now Diageo owns 100% of Ciroc and DeLeón. It’s estimated that Diddy made about $60 million annually from the deal, according to reports.
With a former stage name of Puff Daddy, it should come as no surprise that Diddy has also been invested in the cannabis industry. In November 2022, he inked a $185 million deal to buy cannabis retail stores and production facilities in several U.S. states—including New York, Illinois, and Massachusetts—from Cresco Labs and Columbia Care, two of the nation’s top cannabis brands.
Properties
Diddy has two homes: one in Miami and one in Los Angeles. But he also has an “extensive property portfolio” of multimillion-dollar homes, according to Realtor.com.
In 2021, he bought a $35 million waterfront property from Gloria and Emilio Estefan in Miami. But that’s not the first home he’s bought in the Star Island neighborhood. In 2003, he bought the home next door to the Estefan estate for $14.5 million, which makes Diddy “well on his way to constructing a compound,” according to Realtor.com.
Diddy also owns a $2.7 million condo in Miami and a $39 million mansion in Los Angeles, and previously owned properties in New York City, New Jersey, and Georgia.
Acting and investing
In the early 2010s, Diddy expanded into acting. He costarred in comedy film Get Him to the Greek and appeared on television shows including Entourage, Hawaii Five-0, and It’s Always Sunny in Philadelphia. While there aren’t reports that show how much Diddy made on each of these deals, Get Him to the Greek made $95.5 million in box office sales.
In 2023, Diddy announced a new online marketplace called Empower Global to highlight Black-owned businesses, calling it “Black Wall Street.”
“My dreams have always been to be successful in music, being obsessed with fashion, and the greatest Black serial entrepreneur to ever live,” he said. Time will tell whether he’ll get to keep the spoils of that success.
This story was originally featured on Fortune.com