Sean Diddy Timeline: From building Bad Boy empire to facing lawsuit—how fate overturned music mogul’s destiny

Sean ‘Diddy’ Combs, the music mogul, is making headlines again after a US court on Thursday decided that he will go on trial for racketeering and sex trafficking next year on May 5.

Federal judge Arun Subramanian on October 10 said Diddy will remain incarcerated. This comes after the rapper's indictment last month on three criminal counts alleging he sexually abused women and pushed them into drug-fuelled sex parties using threats and violence.

The rapper made it to the Forbes list of billionaires in 2022 after spending decades in the music industry to build up his legacy through his Bad Boy empire and various side hustles. He is credited with a number of achievements, including five Number ones on the Billboard Hot 100 and 15 hits in the Top 10.

However, the twist of fate came last year when Combs’ ex-girlfriend Casandra Elizabeth Ventura filed a lawsuit against him on November 16, accusing him of sexual misconduct and abuse during their time together. 

The “Me & U” singer, popularly known as Cassie, began dating Diddy around 2007. They ultimately parted ways in 2018 following an 11-year-long on-and-off relationship. Charges that Cassie pressed against Diddy included egregious behaviour with years of abuse and one instance of rape.

The Manhattan federal court lawsuit notes that Cassie “endured over a decade of his violent behaviour and disturbed demands.” This included physical assault and forced "sex acts with male sex workers,” reported Billboard.

This development came just two months after Sean Diddy was honoured with the Global Icon Award at the 2023 MTV Video Music Awards. Within 24 hours of filing the lawsuit, the two reportedly settled the case for an undisclosed amount.

Later, in the same month two other lawsuits were filed against Sean ‘Diddy’ Combs by an anonymous plaintiff. The plaintiff claimed the music mogul sexually assaulted and beat her. The other plaintiff—a woman named Joi Dickerson-Neal—pressed sexual abuse charges and suggested that she had footage of the assault. She accused Diddy of drugging and sexually assaulting her while she was a college student in 1991, Billboard reported.

After three back-to-back sexual and physical abuse lawsuits were filed against Sean Combs, he decided to resign as chairman of the digital media company Revolt, which he helped launch in 2013. 

A fourth lawsuit surfaced in December. A woman named Jane Doe alleged that she was “sex trafficked” and “gang raped” in 2003 when she was 17 years old. She pressed charges against the music mogul, former Bad Boy Records president Harve Pierre and another individual.