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P. Diddy’s Legal Troubles: A Complete Timeline of Scandal and Controversy

By Bobbi Sands
Published May 9, 2025 
Updated 19th May 2025
P. Diddy’s Legal Troubles: A Complete Timeline of Scandal and Controversy

🎯 P. Diddy’s Legal Troubles: A Complete Timeline of Scandal and Controversy

Sean “Diddy” Combs has gone from hip-hop mogul to the center of one of the biggest celebrity legal cases of 2025. Here’s the full timeline of his brushes with the law and the shocking events leading to his current sex trafficking trial.


1999: The Club New York Shooting

  • December 27, 1999: Diddy and then-girlfriend Jennifer Lopez are involved in a nightclub shooting in Manhattan. Combs is arrested and charged with gun possession and bribery after a gun is found in his car.


2001: Cleared of All Charges

  • A New York jury acquits Diddy of all charges. He rebrands from “Puff Daddy” to “P. Diddy” and continues building his empire.


2003–2014: Civil Disputes and Lawsuits

  • Diddy faces multiple business-related lawsuits over contracts and royalties from former Bad Boy Records artists. Most cases are settled privately out of court.


2015: UCLA Kettlebell Incident

  • June 2015: Diddy is arrested at UCLA after allegedly swinging a kettlebell at a football coach during a dispute involving his son Justin.

  • No criminal charges are filed after an internal review.


2023: Cassie Ventura Civil Lawsuit

  • November 2023: Diddy’s former partner, singer Cassie Ventura, sues him, alleging years of physical and sexual abuse, coercion, and control.

  • The lawsuit settles within 24 hours, but triggers federal interest and wider investigations.


2024: Raids and Criminal Indictment

  • March 2024: Federal agents raid Diddy’s homes in Los Angeles and Miami as part of a sex trafficking investigation.

  • September 2024: A federal grand jury indicts Combs on five counts: sex trafficking, racketeering conspiracy, and transportation for prostitution.

  • Diddy is arrested and denied bail multiple times due to fears of witness tampering.


Late 2024: Business Fallout

  • Diddy steps down from Revolt TV and other business ventures amid mounting allegations and public pressure.


May 2025: Federal Trial Begins

  • May 5, 2025: The high-profile trial opens in Manhattan federal court.

  • A list of 190 celebrities—including Kanye West, Michael B. Jordan, Kid Cudi, and Mike Myers—is read to potential jurors to screen for possible bias.

  • Cassie Ventura is the star witness.

  • Federal prosecutors announce that a key accuser, “Victim-3,” has vanished ahead of testimony, raising fears of intimidation.

  • The trial is expected to last eight weeks with multiple accusers and extensive evidence.


May 2025: Returns Key to NYC

  • May 8, 2025: At the request of Mayor Eric Adams, Diddy voluntarily returns the symbolic Key to New York City following intense backlash and criticism.


What Happens Next?

  • Diddy remains held at the Metropolitan Detention Center in Brooklyn as the world awaits the trial’s outcome.

  • If convicted, the once-celebrated music mogul could face decades behind bars, marking a dramatic fall from grace.

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