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The Sean ‘Diddy’ Combs story, from recording studio to courtroom: A timeline

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The Sean ‘Diddy’ Combs story, from recording studio to courtroom: A timeline

Sean “Diddy” Combs, a dominant figure in hip-hop known for discovering the Notorious B.I.G. and founding the influential Bad Boy Records, now faces a pivotal moment in his career. The music mogul, currently 55 years old, is slated to begin trial in New York regarding serious allegations. He stands accused in a federal case of running a multi-decade conspiracy involving racketeering and sex trafficking.

Combs has maintained his innocence throughout the proceedings, entering a plea of not guilty to all charges. This legal battle marks a dramatic turn, tracing his trajectory from a celebrated music industry A-lister to a criminal defendant.

His rise in the music world began in 1993 when he established Bad Boy Records, notably bringing rapper Christopher Wallace, famously known as the Notorious B.I.G., aboard from their previous label connection. Operating under the name "Puff Daddy," Combs launched his debut solo album, "No Way Out," in 1996, which went on to earn a Grammy Award for best rap album.

However, legal troubles started appearing in the late 1990s. In 1999, he pleaded guilty to harassment in New York state court following an attack on another rapper’s manager, receiving a sentence of one day of anger management. Months later, he was charged with weapons offenses after a shooting at a Times Square club but was acquitted at trial. A Detroit radio host sued him for assault in 2001, alleging his associates caused harm and destroyed an interview tape; Combs denied the claims and was cleared by a jury. In 2003, a lawsuit from a former business partner claiming threats with a baseball bat was dismissed on appeal due to the statute of limitations.

Subsequent years brought further legal entanglements. In 2008, Combs privately settled a lawsuit brought by a man who alleged the mogul punched him outside a Hollywood nightclub. He was arrested for aggravated assault in 2015 following an argument with his son’s football coach in Los Angeles, though these charges were later dropped. A former personal chef filed a lawsuit against him in 2017 for sexual harassment and retaliation, which was settled for an undisclosed amount two years later.

A significant wave of lawsuits began in late 2023. On November 16, 2023, Combs' former girlfriend, Cassie Ventura, filed a lawsuit in New York federal court detailing allegations of rape, sex trafficking, and physical abuse. This case was settled privately just days later. Shortly after, on November 23, 2023, Joi Dickerson-Neal filed a lawsuit claiming Combs drugged and raped her in 1991 when she was a university student. This suit was reportedly one of dozens of sexual abuse lawsuits Combs would ultimately face.

More developments followed in 2024. On May 17, CNN released video footage that appeared to show Combs physically assaulting Ventura at a Los Angeles hotel in March 2016. Two days later, on May 19, Combs posted an apology video online addressing the incident with Ventura, stating his actions were "inexcusable" and expressing deep regret. By October 14, an attorney representing 120 individuals filed six new civil lawsuits accusing Combs of various forms of abuse.

The legal challenges escalated on September 16, 2024, when Combs was arrested in New York and charged with racketeering, sex trafficking by force, and transportation for purposes of prostitution. He pleaded not guilty the following day and was denied bail by a judge. Federal prosecutors in Manhattan filed an expanded indictment against him on April 4, 2025, adding five criminal counts. Combs again pleaded not guilty two weeks later.

Most recently, on May 5, 2025, the trial officially commenced with jury selection before US District Judge Arun Subramanian in Manhattan federal court.

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