Sean Combs, also known by various monikers such as Puffy and Diddy, rose from a troubled childhood in Harlem and Mount Vernon to become a towering figure in the hip-hop industry, despite being embroiled in numerous controversies. His first major controversy was the tragic 1991 City College basketball game incident, where nine people died due to overcrowding, for which he faced wrongful death suits but never fully accepted responsibility. Over the years, Combs has repeatedly faced allegations of violence and misconduct, including high-profile incidents in nightclubs and altercations with rival executives, which often resulted in settlements or acquittals. Currently, he is facing his most serious legal challenges with federal charges of sex trafficking and racketeering, alongside more than 50 civil suits for sexual abuse, which could lead to life imprisonment if convicted. Despite his legal troubles, Combs maintained a flamboyant lifestyle and immense influence in the music and fashion industries, although recent revelations and publicized incidents have dramatically shifted public perception against him.

Sean Combs's ascent to fame began in the 1990s, marked by his involvement in the development of hip-hop soul and the launch of his own label, Bad Boy Records, where he promoted artists like Mary J. Blige and the Notorious B.I.G., merging hip-hop with R&B to create a commercially successful sound.

The City College tragedy in 1991, where nine people died in a stampede at an event he promoted, was a significant early controversy; although he contributed to a settlement, Combs never fully accepted responsibility, attributing the chaos to broader community issues rather than his planning failures.

Throughout his career, Combs has faced multiple allegations of violence, including assaults on rival executives, incidents involving firearms, and threats against colleagues, which have been largely settled out of court or dismissed, allowing him to maintain a high-profile public image.

In recent years, Combs has been indicted on federal charges of sex trafficking, racketeering, and related crimes, accused of running a criminal enterprise involving coerced sexual encounters; these charges, along with numerous civil lawsuits, represent the most severe legal challenges he has faced.

Combs's personal brand, characterized by extravagant parties and a lavish lifestyle, has been severely tarnished by the release of video evidence showing violent behavior towards his former girlfriend, Cassie, shifting public and legal scrutiny heavily against him as he awaits trial.