From Mogul To Defendant: The Stunning Fall Of Sean "Diddy" Combs

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Sean “Diddy” Combs was riding high in 2023 — fresh off the release of The Love Album: Off the Grid and receiving a symbolic key to New York City — when explosive allegations from his ex-girlfriend, Cassie Ventura, changed everything.

Though Combs swiftly denied the accusations and settled the lawsuit just a day after it was filed, Ventura is now expected to be a crucial witness in his looming federal criminal trial. Since Ventura’s initial civil suit, the saga around Combs has only intensified: multiple new accusers have come forward, federal raids were conducted on his properties, damning surveillance footage surfaced, and Combs now faces serious criminal charges that could imprison him for life.

Here’s a detailed look at how the Bad Boy mogul’s glittering empire unraveled.

From Icon to Indictment: A Timeline of Diddy's Fall

September 15, 2023: Diddy released The Love Album: Off the Grid, featuring star collaborators like Justin Bieber, The Weeknd, and Mary J. Blige. To honor the moment, New York City Mayor Eric Adams presented him the key to the city, hailing him as the "Bad Boy of Entertainment."

November 16, 2023: Cassandra "Cassie" Ventura, Diddy’s former girlfriend, filed a federal lawsuit accusing him of rape, physical assault, emotional abuse, and manipulation. The shocking complaint alleged years of control and violence, including a brutal 2016 hotel altercation where Diddy allegedly beat her and threw glass vases at her.

November 17, 2023: Just 24 hours later, the lawsuit was settled. Both sides issued statements calling the resolution "amicable," and Combs’ legal team insisted the settlement was "in no way an admission of wrongdoing."

November 23, 2023: Two more women, Joi Dickerson-Neal and Liza Gardner, filed lawsuits accusing Diddy of sexual assault under New York’s Adult Survivors Act, which allowed historic claims to be brought forward.

December 6, 2023: In a since-deleted Instagram post, Diddy declared, "ENOUGH IS ENOUGH," denying all accusations and vowing to fight for his reputation.

March 25, 2024: Federal agents stormed Combs’ homes in Los Angeles and Miami, executing search warrants related to an ongoing sex trafficking investigation.

May 17, 2024: CNN published 2016 hotel surveillance footage showing Combs violently assaulting Ventura — dragging her by the neck, kicking her, and throwing objects at her.

May 19, 2024: Facing public backlash, Combs released an emotional apology video admitting his actions in the footage were "inexcusable." He acknowledged seeking therapy and rehabilitation, though the video was later deleted.

May 29, 2024: Reports emerged that federal prosecutors were preparing to present Combs' accusers to a grand jury.

June 10, 2024: Under pressure, Combs returned his key to New York City after Mayor Adams expressed being "deeply disturbed" by the assault footage.

September 11, 2024: Singer Dawn Richard, formerly of Danity Kane, filed her own lawsuit alleging sexual battery, harassment, false imprisonment — and claimed she witnessed Diddy physically abusing Ventura in the 2000s.

Arrest and Federal Indictment

September 16, 2024: Combs was arrested in New York City following a grand jury indictment charging him with racketeering conspiracy, sex trafficking, and transporting individuals for prostitution — offenses allegedly spanning back to 2008.

September 17, 2024: A sweeping federal indictment accused Diddy of orchestrating a "criminal enterprise" involving sex trafficking, forced labor, bribery, obstruction, and more. Authorities claimed he organized "Freak Offs" — prolonged drug-fueled sex sessions between victims and sex workers — and found weapons, narcotics, and over 1,000 bottles of lubricant during the March raids.

September 18, 2024: Denied bail, Combs remained in federal custody amid concerns over potential witness tampering. Attempts to appeal the decision were unsuccessful.

January 30, 2025: Prosecutors filed a superseding indictment, expanding the racketeering allegations to include two additional female victims, pushing the alleged criminal conduct back to 2004.

March 14, 2025: An aging, gray-haired Combs pleaded not guilty to the expanded charges in court.

April 4, 2025: Another superseding indictment introduced two additional counts of sex trafficking tied to incidents occurring between 2021 and 2024.

April 14, 2025: Combs once again pleaded not guilty.

April 25, 2025: A federal judge ruled that the violent hotel video showing Combs assaulting Ventura would be presented to the jury. It was also revealed that Combs had rejected a plea deal, though details remain under wraps.

May 5, 2025: Jury selection for Diddy's high-profile federal trial began in Manhattan, with proceedings expected to span several weeks.

The Road Ahead

Once celebrated as a visionary music mogul, Diddy now faces the fight of his life in a courtroom. With Ventura and others set to testify and damning evidence mounting, his future hangs precariously in the balance.

If convicted on all counts, the once-untouchable king of Bad Boy Records could spend the rest of his life behind bars.

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