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

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Here's a look at Diddy's rise and fall from music industry A-lister to criminal defendant

Sean “Diddy” Combs, the hip-hop mogul who discovered the Notorious B.I.G. and ran one of the genre’s most iconic record labels, is set to stand trial in New York on Monday in a case accusing the one-time industry kingmaker of running a multi-decade racketeering and sex-trafficking conspiracy.

Combs, 55, has pleaded not guilty and denied wrongdoing.

Here is a timeline of his rise and fall from music industry A-lister to criminal defendant:

1993

Combs establishes his record label Bad Boy Records, bringing along rapper Christopher Wallace (the Notorious B.I.G.) from their former label.

1996

Under the name “Puff Daddy,” Combs releases his first solo album, titled No Way Out, which later wins a Grammy Award for best rap album.

1999

Combs pleads guilty in New York state court to harassment for attacking another rapper’s manager and is sentenced to one day of anger management class. Several months later, Combs is charged with weapons offenses over a shooting at a club in New York’s Times Square, but is acquitted at trial.

2001

A Detroit radio host sues Combs for assault, claiming the rap mogul’s associates roughed him up and destroyed an interview tape. Combs denies wrongdoing and is ultimately cleared by a jury.

2003

A former business partner sues Combs for allegedly threatening him with a baseball bat. Combs denies the allegations, and the case is dismissed after an appeals court finds the statute of limitations had expired.

2008

Combs privately settles a lawsuit by a man who claimed the mogul punched him outside a Hollywood nightclub.

2015

Combs is arrested for aggravated assault after an argument with his son’s football coach in Los Angeles. The charges are later dropped.

2017

Combs’ former personal chef sues the mogul for sexual harassment and retaliation. The case is settled for an undisclosed amount two years later.

November 16, 2023

Combs’ former girlfriend Cassie Ventura sues Combs in New York federal court for rape, sex trafficking and physical abuse. Combs and Venturasettle the case for an undisclosed sum days later.

November 23, 2023

A California woman named Joi Dickerson-Neal files a lawsuit accusing Combs of drugging and raping her when she was a university student in 1991, one of dozens of sexual abuse lawsuits Combs would ultimately face.

May 17, 2024

CNN releases footage purporting to show Combs violently assaulting Ventura at a hotel in Los Angeles on March 5, 2016.

May 19, 2024

Combs posts an apology video for the Ventura incident, saying he is “truly sorry” for his “inexcusable” actions.

October 14, 2024

Combs is accused of assault in six new civil lawsuits filed by an attorney who said he was representing 120 people who accused Combs of abuse.

September 16, 2024

Combs is arrested in New York and charged with racketeering, sex trafficking by force and transportation for purposes of prostitution. He pleads not guilty the following day, and a judge denies him bail.

April 4, 2025

Federal prosecutors in Manhattan file an expanded indictment charging Combs with five criminal counts. Combs pleads not guilty two weeks later.

May 5, 2025

Combs’ trial begins with jury selection before US District Judge Arun Subramanian in Manhattan federal court. – Rappler.com