The Sean “Diddy” Combs trial begins tomorrow, and the timeline behind his legal downfall reads like a true-crime saga. From explosive lawsuits to a five-count federal indictment, here’s a full breakdown of Diddy’s legal timeline and how it all led to a courtroom showdown that could change his life forever.
The wave began in late 2023 and has intensified into a full-scale federal case heading to trial in May 2025. Here’s a full timeline of key events, from the first major civil suit by Cassie Ventura to the current five-count federal indictment against Diddy, as he gets ready for trial.
Diddy Trial Timeline: Every Major Lawsuit and Federal Charge Explained
November 16, 2023
Cassie Ventura, Combs’s ex-girlfriend, filed a bombshell civil lawsuit in federal court. She accused Combs of a decade-long pattern of physical, sexual, and emotional abuse – alleging he beat her, raped her, and forced her into sex with male workers while he watched and filmed. The claims were graphic and disturbing, describing cycles of coercion and trafficking. Combs denied all allegations, calling them blackmail. Within 24 hours, the case was settled privately and dismissed with no admission of guilt.
November 23, 2023
Two more lawsuits dropped the same day. Joi Dickerson-Neal sued under New York’s Adult Survivors Act, claiming Combs drugged and raped her back in 1991 while she was in college. She alleged he videotaped the assault and shared it. That same day, Liza Gardner filed another civil suit, saying Combs and a singer–songwriter gang-raped her in the 1990s and later stalked and attacked her again. Both women’s claims were called “fabricated” by Combs’s legal team. Both cases remain pending.
December 6, 2023
An anonymous woman filed a suit as “Jane Doe,” claiming that in 2003, when she was just 17, she was sex trafficked and gang-raped by Combs and two associates. She alleged she was drugged and flown to New York on a private jet, where the abuse occurred. Combs took to Instagram to call the accusations “sickening lies” and insisted he never did “any of the awful things being alleged.” The case is still in progress.
February 26, 2024
Music producer Rodney “Lil Rod” Jones filed a $30 million civil suit, alleging Combs sexually harassed and drugged him during their work on a 2022–2023 album. He claimed Combs groped him and tried to “groom” him for sex with another man, saying such behavior was “normal” in the industry. Combs’s attorneys moved to dismiss, calling the suit a “shameless” attention grab. In September 2024, a judge threw out some claims, but others are still active.
March 25, 2024
Federal agents raided Combs’s homes in Los Angeles and Miami Beach as part of a Homeland Security-led investigation into sex trafficking. They seized electronics and interviewed past accusers, signaling the feds were closing in. The Department of Justice had begun to connect the dots between the civil suits and a broader criminal pattern.
September 16, 2024
Combs was arrested in New York and indicted on three federal charges – racketeering conspiracy, sex trafficking, and transporting individuals for prostitution. The DOJ described a criminal enterprise dating back to 2008, accusing Combs of using intimidation, coercion, drugs, and abuse to exploit women and men. They said his Bad Boy empire was a front for trafficking, arson, and more. He pleaded not guilty and has been jailed without bail since.
October 1, 2024
Reports emerged that a legal team was preparing to file over 120 additional civil lawsuits against Combs, involving both women and men and spanning the 2000s and 2010s. At least 25 of the alleged victims say they were minors when the abuse happened. The legal pressure on Combs continued to build.
October 10, 2024
A judge set Combs’s criminal trial to begin May 5, 2025, with opening statements due May 12. Prosecutors revealed that part of their case involves so-called “Freak Offs” – events where Combs allegedly flew in people across state lines for drug-fueled sex shows, which were filmed. His attorneys maintain all encounters were consensual.
April 14, 2025
The government expanded the indictment to five counts. Combs again pleaded not guilty. His lawyers called the new charges “recycled” versions of old claims made by the same accusers.
May 1, 2025
At a pre-trial hearing, Combs officially rejected a plea deal. Prosecutors said that decision could now expose him to significantly harsher penalties if convicted. With jury selection imminent, Combs reaffirmed his not-guilty plea.
Throughout all of this, Diddy has denied every accusation. His legal team insists the claims are false, financially motivated, or orchestrated for publicity. In March 2024, attorney Ben Brafman called the federal probe “offensive and outrageous.”
Combs himself declared, “I did not do any of the awful things being alleged.”
Still, prosecutors allege a consistent pattern – dozens of civil suits and a sweeping federal indictment paint a picture of coercion and abuse tied to Combs’s fame and power. Whether he walks free or faces years behind bars will be determined in court this May.
