Sean “Diddy” Combs once stood at the pinnacle of global music and business but today, the 55-year-old rap mogul begins a prison sentence of more than four years, a stunning downfall for a man whose name was once synonymous with wealth, celebrity, and influence.

In the 1990s, Combs—then known as Puff Daddy—helped redefine hip-hop culture.

As founder of Bad Boy Records, he launched the careers of stars including Notorious B.I.G., Mase and Faith Evans, shaping the sound of a generation.

His 1997 tribute “I’ll Be Missing You,” recorded after Biggie’s death, topped charts worldwide and cemented his reputation as both artist and impresario.

Beyond music, Combs expanded into fashion with his Sean John clothing line, winning a Council of Fashion Designers of America award.

He invested in beverages, media and lifestyle ventures, building an empire that Forbes once valued at hundreds of millions of dollars.

His flamboyant persona—complete with luxury parties, mansions and high-profile relationships—made him one of the most recognisable figures in entertainment.

But in recent years, cracks began to show with Combs faced a series of lawsuits alleging sexual abuse and misconduct, alongside investigations into his business dealings.

His arrest in September 2024 marked the sharpest turn: federal prosecutors accused him of running a web of coercion and exploitation.

Though he was acquitted of racketeering and sex trafficking, his July 2025 conviction on charges of transporting people for prostitution sealed his fate.

This week, a New York judge, Arun Subramanian, sentenced him to 50 months in prison, with a hefty fine and five years of supervised release.

After sentencing in court, Combs apologised tearfully, describing his behaviour as “shameful and sick”, but for many, the damage was already done.

His once-glittering empire lies in ruins, endorsements have vanished, and his legacy is overshadowed by scandal.

From many platinum records and designer runways to a federal prison cell, Sean Diddy Combs’ story is now a cautionary tale of power, excess, and accountability.