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Sean Combs - the rise and fall of a man called Diddy

Sean Combs faces life in prison if found guilty of federal charges
Sean Combs faces life in prison if found guilty of federal charges

For a man with so many aliases, it has always been difficult to know who the real Sean Combs really is.

The hugely successful music producer, rapper, and entrepreneur has long been a symbol of music industry wealth and bravado, but a fuller picture of who he is emerged during his seven-week trial for racketeering conspiracy, sex trafficking and transportation to engage in prostitution in New York.

Combs has now been convicted of transportation to engage in prostitution but acquitted of racketeering conspiracy and two counts of sex trafficking,

However, things are now very real for the man who built his name into a global brand, nurtured a reputation as an eccentric multi-millionaire and cultivated a public image of untouchability.

Once a music mogul at the height of global fame, Sean Combs now awaits trial in of the most closely watched celebrity cases in recent memory

Earlie this year, at a hearing in Manhattan federal court, Combs confirmed he had rejected the prosecutors' offer for a plea deal, choosing instead to face trial in a bid to clear his name.

Back then, dressed in a tan-coloured prison garb, the 55-year-old father of seven cut a lonely figure, stripped of the finery and ostentatious displays of bling that are the hallmarks of a certain breed of rappers and music kingpins.

Assuming names like Puff Daddy, P. Diddy and Love, Combs is famous for helping to bring hip-hop and rap crashing into mainstream global culture and making stars of artists like the late Notorious B.I.G. (Biggie Smalls) and Mary J. Blige.

Sean Combs has won numerous awards including three Grammys, two BET Awards and two MTV Video Music Awards

Prosecutors had alleged that Combs used his business enterprises to coerce women into non-consensual sexual encounters, often under the influence of drugs, described by the prosecutors as organised "Freak Offs" spanning over two decades.

The Bad Boy Records founder's defence lawyers had strongly disputed these claims, maintaining that any sexual activity was consensual and occurred in the context of his personal relationships and private lifestyle. They said the accusations were distorted and that Combs was eager to defend his name in court.

Sean Combs and Mary J. Blige, one of the many artists whose careers he helped shape during his rise to music industry dominance

The entrepreneur, rapper, fashion and drinks brand owner, who is most famous for sampling a Police song for his biggest hit, found himself under a different spotlight - not as a mogul but as a defendant.

His bulging Rolodex of nicknames and aliases, of course, have long been part of hip-hop showmanship, but unlike, say, Messrs Ice (T and Cube, not Vanilla), Combs was always a businessman first and rapper second. Critics and supporters alike acknowledge his relentless business focus as both a strength and now a source of scrutiny.

He was born Sean John Combs on November 4, 1969, in Harlem, New York City and was raised by his mother after his father was murdered in 1974.

The rapper and actor recieved a star on the Hollywood Walk of Fame in 2008

After attending a Catholic boys' school in the Bronx, he majored in business administration at Howard University. Signs of his hugely impressive gift for business began early - he held weekly dance parties and ran an airport shuttle service while attending classes.

However, he dropped out of college when he landed an internship at Uptown Records, the New York label founded in 1986 by former rapper Andre Harrell. The label specialised in the growing popularity of R&B and hip-hop.

In a talent management position, the young Diddy was immediately successful and rose to become vice president and had success producing several key artists for Uptown, but left the company in the early 1990s.

Sean Combs and Jennifer Lopes pictured together during thier high-profile relationship in the 1990s

He already had bigger plans and in 1993, he founded his own production company, Bad Boy Entertainment and began working with Mariah Carey, Babyface, TLC, Boyz II Men, Lil' Kim, Aretha Franklin, Mary J. Blige, and Biggie Smalls.

At the height of the West Coast v East Coast hip hop feud, Smalls was murdered in 1997, and it inspired Combs to record the tribute I’ll Be Missing You, which sampled Every Breath You Take by The Police and became his most famous and biggest-selling song.

His first album, No Way Out, followed in the same year, with his second album, Forever, released in 1999. By then, Combs’s own bad boy lifestyle was beginning to leak out into his personal life. In December 1999, he and his then-girlfriend, Jennifer Lopez, were allegedly present at a shooting incident at a New York City nightclub. Combs was later charged with four counts of illegal gun possession and one count of bribery, but was cleared of all charges in 2001.

Sean Combs with The Notorious B.I.G., the legendary rapper whose rise was closely tied to Combs' Bad Boy Records and whose death in 1997 deeply impacted the music world

Further albums followed, including Press Play, which featured Brandy, Mary J. Blige, and Timbaland. Combs has also appeared in numerous movies, often as himself, such as Monster's Ball (2001), Carlito’s Way: Rise to Power (2005), Get Him to the Greek (2010), Muppets Most Wanted (2014), and Girls Trip (2017). He has also appeared on shows such as CSI: Miami, Hawaii Five-O, and It’s Always Sunny in Philadelphia.

His business interests expanded into an empire. He founded his own clothing line, Sean John, and he has had interests in the drinks industry for many years, including a deal with the vodka brand Cîroc and a less successful venture with a tequila brand.

Combs, whose fortune was valued at $600 million by Forbes in 2024, is a father to seven children from four different relationships. His high-profile romances have included stylist Misa Hylton, Kim Porter, Jennifer Lopez and Cassie Ventura. He has also been romantically linked to Cameron Diaz and Naomi Campbell.

Sean Combs performing at the MTV Video Music Awards in 2023 were he was honoured with the Global Icon award

It was a recently released security video - showing an altercation between Combs and Ventura at a Los Angeles hotel in 2016 - that reignited public and legal scrutiny. Combs apologised for his behaviour, calling it "inexcusable", but the footage led to renewed attention on previous and new allegations.

The case became a flashpoint in discussions about accountability and power dynamics within the music industry, particularly in the era following the #MeToo movement.

Combs's convictions now throw a dark veil over certain aspects of the culture and politics of nineties and early noughties hip hop - a genre now increasingly shaped by women with strong voices and agency.

Sean Combs arriving at the 'Real' White Party in September 2007

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