Once a hip-hop king, Sean ‘Diddy’ Combs faces trial that could send him to prison for life

Sean "Diddy" Combs, a pivotal force in elevating hip-hop's place in American culture and the architect behind a vast music and fashion empire that saw him reach billionaire status, is now facing a sex trafficking trial. Opening statements are set to begin on Monday for the 55-year-old mogul, a legal battle that could either solidify his severely damaged public image or, less likely, offer a path towards potential recovery.

Combs is among the most recognized and influential figures in entertainment to face serious sexual abuse allegations in the wake of the #MeToo movement, which empowered individuals to come forward. Similar to cases involving movie producer Harvey Weinstein and R&B singer R. Kelly, prosecutors allege that Combs leveraged his considerable influence and wealth to coerce women into unwanted sexual activity and then used intimidation tactics to keep them silent for years.

He has entered a plea of not guilty to five felony counts, including racketeering conspiracy and sex trafficking. The trial is taking place in Manhattan federal court and is anticipated to potentially span two months. His legal representatives did not provide a comment for this report.

Since his arrest in September, Combs has been held in Brooklyn, a considerable distance from the luxurious homes he maintained in Miami and Los Angeles, but roughly an hour via subway from the Harlem neighborhood where he was born and raised by a single mother after his father passed away when he was four.

Combs left Howard University after two years to pursue a career in the music industry, working at Uptown Records before co-founding Bad Boy Records in 1993. Known for his flair as both a hustler and showman, he was instrumental in launching the careers of artists like Mary J. Blige, Faith Evans, Notorious B.I.G., and Usher, significantly broadening hip-hop's mainstream appeal throughout the 1990s and 2000s.

His lifestyle was characterized by extravagance, including diamonds, yachts, and elaborate parties, attracting musicians, athletes, and actors eager to join his circle. In the late 90s, his relationship with singer Jennifer Lopez made them one of entertainment's prominent power couples. Author Mark Anthony Neal noted in the documentary "The Fall of Diddy" that Combs made hip-hop feel so vibrant and essential to American culture that everyone wanted a part of it.

Combs earned three Grammy awards, including one for "I'll Be Missing You," his 1997 tribute following Biggie's death. Building on his fame, he launched the successful Sean John clothing line and the Revolt TV cable network. In 2004, he even took to the Broadway stage, starring in "A Raisin in the Sun." While Combs has sold his interest in Revolt, a spokesperson did not comment on the current status of Sean John.

By 2022, Forbes estimated Combs' net worth had reached over $1 billion, positioning his journey from humble beginnings to immense wealth as an inspiring narrative, particularly for other Black men. That same year, he was presented with a lifetime achievement honor at the BET Awards, where he stated, "Anything I do is through love."

However, prosecutors present a starkly different picture. They assert that Combs, leveraging his extensive business network, compelled women to participate in disturbing sexual acts referred to as "Freak Offs" involving male sex workers between 2004 and 2024. They claim he facilitated these events by providing drugs like ketamine and ecstasy to the women, alongside promises of financial, career, or romantic support.

Prosecutors allege that Combs would observe these acts, sometimes record them, and masturbate. They further contend that he utilized these clandestine recordings of sexual encounters as "collateral" to ensure the women's silence and on occasion displayed weapons to further intimidate them.

Marc Agnifilo, a lawyer for Combs, has previously maintained that the sexual activity described by the prosecution was consensual.

Among the key witnesses expected to testify for the prosecution is Casandra Ventura, an R&B artist and Combs' former girlfriend, known professionally as Cassie. Ventura filed a lawsuit against Combs in November 2023, alleging rape and persistent physical abuse over their decade-long professional and romantic relationship. Combs denied these allegations, but the lawsuit was settled the day after it was filed; details of the settlement were not disclosed.

Subsequently, CNN broadcast hotel surveillance footage that appeared to show Combs assaulting and dragging Ventura, leading to a public apology from Combs. Dozens of other civil lawsuits alleging sexual abuse have also been filed against Combs by both women and men, all of which he denies. By 2024, Fortune magazine estimated Combs' net worth had dropped to approximately $400 million.