Photo Credit: Giorgio Trovato

Sean ‘Diddy’ Combs has watched his net worth skyrocket over 30-plus years, but that may rapidly dwindle in the face of legal trepidation and federal raids on his properties.

Just weeks after the latest lawsuit emerged accusing Sean “Diddy” Combs of sexual misconduct and trafficking, Homeland Security raided the music industry mogul’s homes in Miami and Los Angeles. Details of that investigation are sparse, but they stem from allegations found in the many lawsuits filed against him in recent months, beginning with charges from Combs’ former partner, singer Cassie Ventura.

Combs and his attorney have disputed each of the allegations raised against him, but even before the raids on his properties, it seemed the damage to his reputation was already done. In 2022, Forbes estimated Combs’ net worth at $1 billion, but the end of his highly lucrative partnership with spirits giant Diageo in January of this year had already brought that estimate down to $800 million.

Since Adidas ended their partnership with disgraced rapper Kanye West, Combs was the second richest man in hip-hop in October 2022, behind Jay-Z — and similar to Jay-Z, Diddy’s wealth is largely attributed to business ventures beyond music.

Combs had early success as a producer, beginning as an intern at New York’s Uptown Records in 1990, where he helped develop acts like Mary J. Blige. After a significant career setback in 1991 — an AIDS fundraiser he promoted at Harlem’s City College majorly oversold, resulting in a crowd crush event that killed nine people, leading to Uptown Records firing him — he started his own company, Bad Boy Records, in 1993. Bringing fellow Uptown signee the Notorious B.I.G. with him, Combs’ Bad Boy production crew was soon working with artists like Aretha Franklin, Boyz II Men, Lil Kim, and Usher.

As an artist, Combs’ most successful release remains his debut studio album, No Way Out, released in 1997 following the murder of the Notorious B.I.G. It peaked at No. 1 on the Billboard 200 and saw five nominations at the 40th Grammy Awards, winning Best Rap Album.

Though Combs continued releasing music, his wealth grew significantly as he diversified his portfolio with many business opportunities. In 1998, he founded his Sean John clothing line, of which he sold a 90% stake to Global Brands Group in 2016, but reacquired in 2021 for $7.5 million. In 2008, he acquired the Enyce clothing line from Liz Claiborne in a $20 million deal.

He began a particularly lucrative partnership with British spirits company Diageo in 2007, with whom he collaborated to promote their Cîroc Vodka brand and became joint owner of their DeLeón Tequila brand. At the peak of his success in the alcohol business, he founded Combs Wines and Spirits in 2013. However, his partnership with Diageo came to a close in January 2024, ending an intense several-month legal battle stemming from racial accusations Combs levied against the company.

Combs also dipped his toe into the acting pool, appearing in films like 2010’s Get Him to the Greek, and TV shows such as Hawaii Five-O and It’s Always Sunny in Philadelphia. He also co-founded the Black culture-focused television network, Revolt, which he recently divested to an unknown buyer.

Recently, most of Combs’ time spent in the spotlight has been fighting several legal battles, many of which accuse him of sexual assault and trafficking. The first such lawsuit, filed by singer and Combs’ ex-girlfriend Cassie Ventura, was quickly settled — but like Hercules cutting off the Hydra’s head, several more popped up in its place.

In February, a lawsuit filed by music producer Rodney Jones contains perhaps the most damning accusations, asserting to the existence of hours of audio and video footage of Combs and his team engaging in illicit activity. Jones’ lawsuit alleges that he was sexually harassed, coerced into soliciting sex workers, drugged, and threatened, for more than a year during his time working with Combs on his recent Love Album.

Combs’ attorney has disputed the allegations, calling them “lies,” and asserting Diddy’s innocence. But the recent raids on his property and involvement of Homeland Security implies that things are far from over, and Combs’ net worth may yet continue to take a dive.