30 Years of Career, Peek at 13 Controversies of Sean Diddy Combs That Caused a Stir - Always Escaping the Law

The heated rivalry between the West Coast and East Coast is said to be the cause of the deaths of Tupac and Biggie. In 1996, Tupac was attacked by a group of armed gangsters and ultimately died at the age of 25. The West Coast accused Biggie and the head of Bad Boy Records, Puff Daddy a.k.a Diddy, of being the masterminds behind Tupac's murder. Six months after Tupac's death, Biggie lost his life. The issue of revenge for Tupac's death was loudly echoed in the aftermath of Biggie's death. 

Steve Stoute, who once served as an executive at Interscope Records, claimed that Diddy and his bodyguard attacked him with champagne bottles, a phone, chairs, and punches in 1999, as a result of the controversial footage used in Nas's video titled 'Hate Me Now'. Diddy could face up to seven years in prison if found guilty of the assault, but Steve Stoute requested the Manhattan district attorney to drop the charges after he publicly apologized.

In December 1999, a fight occurred at a nightclub in Manhattan, where Diddy was spending the night with Jennifer Lopez, who was his girlfriend at the time. At least two people were injured due to gunfire. Several witnesses stated that Diddy had been holding a gun, which led to his charges of gun possession and bribery, but he was later acquitted. Instead, his former protégé, rapper Shyne, was sentenced to 10 years in prison for assault, gun possession, and recklessly endangering others.

A report in 2003 revealed that workers at Sean John, Diddy's fashion company, in a factory located in Honduras had to face poor working conditions. Sean John executives, including Diddy, responded to the report by saying that they were unaware of the issues but would strive to address them.

In 2005, Rogelio Mills, a talk show host, accused Diddy and his associates of assaulting him in 1999. It was said that the trigger for the incident was Rogelio Mills' question about Diddy's role in Biggie's death case. However, the jury decided to side with Diddy, a decision that was upheld on appeal.

The LOX was involved in a dispute with Diddy regarding his mistreatment of artists and his refusal to return their publishing rights in 2005. This moment occurred at Hot 97 in New York, reinforcing claims that Diddy did not provide fair compensation to Bad Boy artists. Although they eventually settled the dispute, Diddy's bad reputation as a record executive still lingers to this day.

In 2006, Diddy, who previously used the stage name P. Diddy, encountered problems when changing his name without prior research. Diddy was unaware that the name "Diddy" was already used by a producer in England, namely Richard "Diddy" Dearlove. After a legal battle, Diddy was required to pay a fine of 100,000 pounds (around 2 billion IDR) and continue using the name P. Diddy while working and creating in England.

In 2007, Diddy was sued for 4 million dollars (around 60.7 billion IDR) by a nightclub promoter who claimed that Diddy had ordered his bodyguard to forcibly "remove" the promoter. The promoter alleged that he was punched, kicked, and chased around the club.

In November 2012, Diddy and Kid Cudi were rumored to be involved in a fight. It was said that the two were competing over a female singer at a Hollywood club. Rumors also circulated that they exchanged heated words, drawing the attention of everyone in the club.

In 2015, Diddy thought a football coach at UCLA was coaching his son, Justin, too harshly. As a result, Diddy allegedly attacked the coach with a kettlebell, which led to his arrest on charges of assault with a deadly weapon. Ultimately, the Los Angeles District Attorney's Office did not file charges in the assault case.

A woman who previously worked as Diddy's personal chef filed a sexual harassment lawsuit in 2017. The woman claimed she was forced to serve food after Diddy had sex, with her former employer still naked. She also accused Diddy of not paying her overtime. In 2019, the lawsuit was settled, though no details were made public.

Diddy criticized the Recording Academy for its lack of recognition and appreciation for the rap and R&B categories at the 2021 Clive Davis Pre-GRAMMY Gala. He described himself as an artist trying to represent his community, but former Bad Boy star, Ma$e, disagreed with his speech. Ma$e responded on Instagram by writing, "Your past business practices continuously leave your artists starving and are very unfair to the same artists who helped you earn the Icon Award at the legendary Bad Boy label." Their past feud came back into the spotlight when Diddy stated that he would return publishing rights to former Bad Boy artists, producers, and songwriters. Several former artists questioned Diddy's motives behind this "kindness".

After building the highly successful Ciroc vodka and DeLeon tequila brands, Diddy accused distributor Diageo of racism by claiming that they did not offer the same resources for Black-owned brands as they did for other brands. In response, Diageo ended its business partnership with Diddy. The dispute has continued, with Diddy using social media to mock Diageo by praising other alcoholic beverage brands.