Sean “Diddy” Combs has never been a squeaky clean celebrity. The rapper/producer has often found himself dealing with controversy or legal trouble. However, the sexual assault allegations recently aimed at the mogul have led to a new level of scrutiny into his past. As we discuss what these accusations mean for the billionaire, we’re exploring his history of controversy and legal trouble.
In the mid ‘90s, rap music was dominated by the ongoing feud between East Coast and West Coast artists; specifically, Bad Boy and Death Row. Insults and diss tracks went back and forth as the tension rose to a dangerous level. Unfortunately, it reached a tragic peak with the murders of Tupac Shakur and Notorious B.I.G., two of the most influential artists in music history. Diddy has never been arrested, charged or credibly connected to either attack, but that hasn’t stopped conspiracy theories from continuing to suggest he was somehow involved.
While attending a New York nightclub with then girlfriend Jennifer Lopez, a shooting at the club caused chaos. Later that night, the couple and two other passengers were stopped by police and ended up charged with “charged with criminal possession of a weapon and possession of stolen property.” J.Lo, whose movie career was just taking off, found herself connected to Combs’ highly-publicized criminal trial and the couple eventually broke up. Puff Daddy was found not guilty and changed his name to P. Diddy.
In 2003, a report revealed that Sean John workers in a Honduras factory were essentially dealing with sweatshop conditions. Sean John executives, including Combs, said they didn’t know about the problems, but would work to fix them.
When P. Diddy became Diddy he forgot to ask around. As it turns out, Richard “Diddy” Dearlove, a producer in the United Kingdom, was already using the name. After a legal battle, there was a “£100,000 settlement in September 2006” and he must remain P. Diddy in the UK.
Detroit talk show host Rogelio Mills alleged that Diddy and his entourage assaulted him in 1999 after he asked about the producer’s role in Biggie’s death. The jury ruled in favor of Combs, a decision upheld on appeal.
The LOX got into it with Diddy about his mistreatment of artists and refusal to return their publishing rights. This moment went down on New York’s Hot 97, cementing the claims that he didn’t fairly compensate Bad Boy artists. Even though they eventually settled the dispute, the reputation for being a predatory record executive follows Diddy to this day.
A nightclub promoter sued the “Coming Home” rapper for $4 million, claiming Diddy had his bodyguard “forcibly remove” the promoter. He alleged his was “punched, kicked and chased around the club.”
In light of Cassie’s allegations, this is particularly disturbing. In November 2012, the two rappers reportedly got into a fight over the singer in a Hollywood club. Rumors say they “exchanged some heated words to the point where the entire club was watching – creating a huge scene.”
After he thought a football coach at UCLA was too hard on his son Justin, Combs allegedly assaulted the man with a kettlebell, leading to the Bad Boy founder’s arrest for assault with a deadly weapon. In the end, the Los Angeles District Attorney’s Office didn’t pursue felony assault charges.
A woman who worked as a former private chef for the music producer filed a sexual harassment lawsuit alleging that she was forced to serve him “post-sex meals while he was naked.” She also accused him of not paying her for long overtime hours. In 2019, the suit was settled, though no details were released.
At Clive Davis’ 2021 Pre-GRAMMY Gala, Diddy decided to call out The Recording Academy for its lack of acknowledgement and appreciation for rap and R&B categories. He portrayed himself as just another artist trying to represent for his people, but former Bad Boy star Ma$e took exception with his speech. He responded on Instagram, writing, “Your past business practices knowingly has continued purposely starved your artist and been extremely unfair to the very same artist that helped u obtain that Icon Award on the iconic Badboy label,” Their long standing beef recently made news again when Combs declared he was returning publishing rights to former Bad Boy artists, producers and songwriters. Some of those former artists have questioned his motives for this “act of kindness.”
After building the extremely successful Ciroc vodka and DeLeon tequila brands, Diddy accused distributor Diageo of racism, alleging they didn’t offer the same resources to Black-owned brands that they did others. In response, Diageo ended its business partnership with Combs. As this dispute has dragged on, Diddy has used social media to throw shade by complimenting other spirit brands.
Cassie Ventura shocked the world when she filed a bombshell lawsuit accusing the mogul of “years of physical abuse,” rape, sexual assault and sexual battery. The details behind their 11 year relationship are extremely disturbing. Combs’ lawyers claim the lawsuit is about money, but these may be the allegations the billionaire can’t make go away.
A day after Cassie filed her lawsuit, Combs settled with his ex. Details of the suit were not disclosed, but Cassie said in a statement, “I have decided to resolve this matter amicably on terms that I have some level of control. I want to thank my family, fans and lawyers for their unwavering support.”
“We have decided to resolve this matter amicably. I wish Cassie and her family all the best,” Combs said in a statement.
With his reputation damaged by these accusations, Diddy is now dealing with the fallout of the allegations. He recently stepped down as chairman of Revolt TV, while Capital Preparatory Schools has ended its partnership with the Bad Boy founder. It remains to be seen what other corporations or entities will cut ties with Combs.