From Power to Prosecution: Timeline of Events in the Rise, Fall, and Reckoning of Diddy

Once hailed as a visionary mogul and a towering figure in hip-hop culture, Sean “Diddy” Combs now finds himself at the center of a high-stakes federal trial that could end his career — and possibly his freedom. Over the past year, a slow-burning storm of allegations and legal battles has erupted into a full-fledged courtroom saga in Manhattan, where Combs stands accused of racketeering, sex trafficking, and more. As the courtroom drama unfolds, we got you covered with a timeline breaking down the key events leading to one of the most significant legal reckonings in modern pop culture.

Let’s get to it …

Build up to a legal reckoning

November 16, 2023

Sean Combs’ longtime ex-girlfriend, Casandra “Cassie” Ventura, ignited the legal firestorm by filing a federal lawsuit accusing him of rape, physical abuse, and a disturbing level of emotional control. The suit detailed harrowing instances of alleged assault — including a 2016 hotel hallway incident — and accused Combs of running a system of coercion and exploitation masked behind fame and wealth. The timing was strategic, filed just days before the expiration of New York’s Adult Survivors Act, which allowed adult victims of sexual abuse to file claims outside of the statute of limitations.

November 17, 2023

In a surprising turn, Ventura and Combs settled the lawsuit less than 24 hours later. Both issued statements claiming the matter was resolved “amicably.” Combs’ legal team emphasized that the agreement was “in no way an admission of wrongdoing.”

November 23, 2023

Two additional women, Joi Dickerson-Neal and Liza Gardner, filed similar lawsuits under the Adult Survivors Act, adding to the mounting accusations. Combs denied all allegations.

December 6, 2023

In an Instagram post since deleted, Combs pushed back. “ENOUGH IS ENOUGH,” he wrote. “Sickening allegations have been made against me by individuals looking for a quick payday… I did not do any of the awful things being alleged.”

March 25, 2024

The investigation took a dramatic turn when federal agents executed coordinated raids on Combs’ residences in Los Angeles and Miami. Tactical units were deployed in a show of force rarely seen in celebrity investigations.

May 17, 2024

CNN released chilling surveillance footage from a 2016 hotel incident showing Combs physically assaulting Cassie Ventura. The footage depicted Combs grabbing her, dragging her across the floor, and kicking her. Ventura remained silent publicly, but her attorney commented: “The gut-wrenching video has only further confirmed the disturbing and predatory behavior of Mr. Combs.”

May 19, 2024

Combs issued a video apology: “My behavior on that video is inexcusable… I’m disgusted now. I went and sought out professional help… I’m truly sorry.”

May 29, 2024

CNN reported that federal investigators had begun preparing accusers to testify before a grand jury. Many civil plaintiffs also cooperated with authorities and submitted evidence.

June 10, 2024

Under public pressure, Combs returned his symbolic key to New York City after Mayor Eric Adams expressed being “deeply disturbed” by the CNN footage.

September 11, 2024

Singer Dawn Richard, formerly of Danity Kane, added her voice to the chorus of accusers, alleging she witnessed Combs “brutally beat” Ventura and also suffered abuse herself.

September 16–18, 2024

Combs was arrested in New York City following a grand jury indictment. The unsealed indictment painted a damning portrait of Combs as the head of a “criminal enterprise” accused of trafficking, forced labor, witness tampering, and obstruction of justice. Among the evidence seized were weapons, drugs, and over 1,000 bottles of lubricant — reportedly used in events described by victims as “Freak Offs.” He was denied bail and has remained in federal custody since.

Judge Andrew Carter, who initially oversaw his detention hearing, ruled against release due to fears of “obstruction of justice and the danger of witness tampering.”

January–April 2025: The Case Expands

Federal prosecutors filed two superseding indictments expanding the time frame and number of victims involved. New charges included additional sex trafficking counts and acts alleged to have taken place between 2004 and 2024. Combs pleaded not guilty at each stage.

April 25, 2025

A pivotal ruling allowed the infamous hotel surveillance video to be shown to the jury. Prosecutors also disclosed that Combs had turned down a plea offer — the terms of which were not revealed.

Trial in Motion: What’s Happening Now

May 5, 2025

Jury selection began in Manhattan’s Southern District Court, presided over by Judge Arun Subramanian. Jurors were questioned about their familiarity with Combs, the 2016 footage, and a surprising list of celebrity names including Kanye West, Kid Cudi, Michael B. Jordan, and Michelle Williams. Their connections to the case remain unclear.

May 12, 2025

Opening arguments laid the stakes bare. Prosecutors presented Combs as the mastermind of a criminal operation that commodified and controlled women. If convicted on all counts, Combs faces life in prison.

May 13, 2025

Cassie Ventura took the stand as the prosecution’s star witness. She recounted years of alleged manipulation and abuse, describing a life dominated by Combs’ orchestrated “freak-offs” — multi-day, drug-fueled encounters with sex workers. Her testimony painted a chilling albeit alleged portrait of control, fear, and psychological torment.

The saga continues … What’s next?

With the trial well underway and more compelling witnesses expected to testify, the next several weeks promise to reshape the legacy of one of hip-hop’s most iconic — and now most controversial — figures. Here’s what we know. Regardless of the outcome, the Combs trial represents a seismic moment in the ongoing reckoning with power, celebrity, and accountability in the entertainment industry.

Stay with The Source for continued coverage as the trial of the century unfolds.