Sean “Diddy” Combs casts a long shadow over the history of hip hop. One of the industry’s first moguls, his work as an A&R executive, label boss, rapper and producer made him both extravagantly wealthy and internationally famous.

Follow live updates on the investigation into Combs here

While Combs, 54, may have spent over thirty years at the top of the industry, the news this week of Homeland Security raids on his homes in Los Angeles and Miami puts his legacy in a different light. He is now facing multiple civil lawsuits accusing him of sex trafficking, sexual abuse and rape. He strongly denies all of the allegations against him, while his attorneys have branded the lawsuits and their accusations as money grabs, “baseless” or “sickening.”

Still, with Combs back in the headlines for all the wrong reasons, old rivalries are resurfacing. Earlier this week, his longtime West Coast sparring partner Suge Knight, who is currently serving a 28-year sentence for manslaughter, tweeted from jail: “Justice for 2Pac is coming Keefe D and now Diddy!!!”

The feud between Combs and Knight was at the heart of the East Coast–West Coast hip hop rivalry of the mid-Nineties. They were at that point each the respective heads of the most influential rap labels on either coast of America. In 1991, Knight co-founded Death Row Records in Los Angeles alongside producers Dr Dre, Dick Griffey and The D.O.C, and with acts like NWA and Snoop Dogg on their roster it seemed to some fans that rap had upped sticks from its historic home in New York and relocated to sun-kissed California.

Two years later, in 1993, Combs was fired from his role as an A&R executive at Uptown Records and decided to start his own label, Bad Boy Records. They quickly had a massive hit with the very first album they released, The Notorious B.I.G.’s Ready to Die, and the focal point of the rap universe seemed to swing back towards the Empire State.

Before long Biggie had established himself as the face of East Coast rap, but he had a rival for the national crown: Tupac Shakur. By the time Biggie released Ready to Die, New York-born Shakur had already relocated to the West Coast and released two acclaimed albums and starred in three films.

Sean ‘Puffy’ Combs at the MTV Europe Music Awards in 1999

(Getty Images)

However, he was also involved in a sexual abuse trial in New York. On 30 November 1994, Shakur arrived at Quad Studios in Manhattan where he was scheduled to record with rapper Little Shawn to help pay his legal fees. When he stepped inside the building two gunmen robbed him, shooting him five times. In the aftermath, Shakur implied in an interview that he believed Biggie and Combs may have been involved in the attack as they saw him as a competitor. Shakur was convicted of the abuse charges and spent time in jail at Rikers Island, where Combs visited him to assure him that Bad Boy Records had not been involved in the shooting.

Things came to a head at the Source Awards in New York the following year, on 3 August 1995. There, Knight famously and publicly took a shot at Combs, needling him for his fondness for appearing in his artists’ music videos and rapping on their songs. “Any artist out there that want to be an artist and want to stay a star, and don’t want to have to worry about the executive producer trying to be all in the videos… All on the records… dancing, come to Death Row!” proclaimed Knight from the stage.

When Combs took the stage later to present another award, he spoke up for unity. “All this East and West – that needs to stop,” he told the audience. “So give it up for everybody from the East and the West that won tonight. One love.”

Amazon Music logo

Enjoy unlimited access to 70 million ad-free songs and podcasts with Amazon Music

Sign up now for a 30-day free trial

Sign up

Amazon Music logo

Enjoy unlimited access to 70 million ad-free songs and podcasts with Amazon Music

Sign up now for a 30-day free trial

Sign up

The Notorious B.I.G. with Combs

(Erik Pendzich/REX)

The rivalry rumbled on throughout the following year, reaching a bloody climax when Shakur was shot in Las Vegas in September 1996, succumbing to his injuries in the following days. Six months later, in March 1997, Biggie was shot and killed in Los Angeles in what was widely seen as retalitation for Shakur’s death.

Both murders went unsolved for many decades, and without a culprit rumours circulated once again that Combs and Bad Boy Records could have been behind Shakur’s shooting. This rumour has refused to go away despite evidence to the contrary, with the likes of Eminem keeping the theory alive when he rapped on his 2018 song “Killshot”, a diss track largely aimed at Machine Gun Kelly: “But, Kells, the day you put out a hit’s the day Diddy admits/That he put the hit out that got Pac killed, ah!” Granted, Eminem does add at the end of the track: “And I’m just playin’, Diddy / You know I love you.” Shakur’s murder may have moved a step closer to being solved last year, when Duane “Keffe D” Davis, 60, was finally arrested and charged with the crime.

If Knight and Combs still didn’t see eye-to-eye, their paths diverged in the aftermath of the death of their two biggest stars. Knight filed for bankruptcy in 2006, bringing Death Row Records as it was to a close (the brand name has since been bought by Snoop Dogg). In 2017, he was convicted of voluntary manslaughter for killing music executive Terry Carter by driving his car into him. He will not be eligible for parole until 2034.

Combs, for a time, seemed to flourish. He had a string of hits in the late Nineties, including his Biggie tribute “I’ll Be Missing You”. He parlayed his rap success into a Hollywood acting career and made serious money from developing the Cîroc vodka brand with beverage company Diageo (splitting profits 50-50) and television network Revolt TV. In 2022, Forbes estimated that with his musical accomplishments and his business ventures, Combs’ net worth totted up to a cool billion dollars.

As of 2024 however, he is no longer involved with either Cîroc or Revolt and his future looks entirely uncertain.