A timeline of the rise of Sean ‘Diddy' Combs and his legal troubles

Winnipeg Free Press

03-07-2025

For more than two decades, Sean 'Diddy' Combs was one of hip-hop's most nimble entrepreneurs, spinning his hitmaking talents into a broad business empire that included a record label, a fashion brand, a TV network, deals with liquor companies and a key role in a reality TV show.
Then he was charged with forcing, threatening and manipulating two ex-girlfriends into drug-fueled sex marathons, with assistance from a network of associates.
Combs denied the allegations and went to trial in a high-stakes federal sex crimes and racketeering case. The trial ended Wednesday with a verdict that his attorneys called a victory: Combs was convicted of prostitution-related offenses but acquitted of higher-level charges of racketeering and sex trafficking.
Here is a timeline of major events in his life story:
1990-1999
1990: Combs, then a student at Howard University, gets his start in the music business with an internship at Uptown Records in New York.
Dec. 28, 1991: Nine people die at a celebrity basketball game promoted by Combs and the rapper Heavy D when thousands of fans try to get into a gym at the City College of New York. A mayoral report lays part of the blame for the catastrophe on poor planning by Combs.
1992: Combs is one of the executive producers on Mary J. Blige's debut album, 'What's the 411?'
1993: After being fired by Uptown, Combs establishes his own label, Bad Boy, which quickly cuts a lucrative deal with Arista Records.
1994: Bad Boy releases Notorious B.I.G.'s album 'Ready to Die.' Two months later, Tupac Shakur survives a shooting in New York and accuses Combs and Biggie of having prior knowledge of the attack, which they deny. Shakur was later killed in a 1996 shooting in Las Vegas.
1996: Combs is convicted of criminal mischief after he allegedly threatened a photographer with a gun.
1997: Biggie is killed in Los Angeles. Combs, then known as Puff Daddy, releases 'I'll be Missing You' in honor of his dead star.
1998: Combs wins two Grammys, one for best rap album for his debut 'No Way Out' and another for best rap performance by a duo or group for 'I'll Be Missing You' with Faith Evans. Also that year, Combs' Sean John fashion line is founded.
April 16, 1999: Combs and his bodyguards are charged with attacking Interscope Records music executive Steve Stoute in his New York office in a dispute over a music video. Combs is sentenced to an anger management course.
Dec. 27, 1999: Combs is arrested on gun possession charges after he and his girlfriend at the time, Jennifer Lopez, fled a shooting that wounded three people at a New York City nightclub. Some witnesses tell police Combs was among the people shooting in the club. He is later charged with offering his driver $50,000 to claim ownership of the 9 mm handgun found in his car.
2001-2008
March 17, 2001: Combs is acquitted of all charges related to the nightclub shooting. One of his rap protégés, Jamal 'Shyne' Barrow, is convicted in the shooting and serves nearly nine years in prison. Two weeks after the trial, Combs announces he wants to be known as P. Diddy. (Barrow also later changed his name, to Moses Barrow, and became a parliamentarian in his native Belize).
2002: Combs becomes the producer and star of 'Making the Band,' a talent search TV show.
Feb. 1, 2004: Combs performs at the Super Bowl halftime show along with Janet Jackson, Justin Timberlake and others. A week later, Combs, Nelly and Murphy Lee win a Grammy for best rap performance by a duo or group for 'Shake Ya Tailfeather.'
April 2004: Combs makes his Broadway acting debut in 'A Raisin in the Sun.'
2005: Combs announces he is changing his stage name to Diddy, getting rid of the P.
March 2008: Combs settles a lawsuit brought by a man who claims Combs punched him after a post-Oscar party outside a Hollywood hotel the previous year. In May, Combs is honored with a star on the Hollywood Walk of Fame.
2015-2022
2015: Combs is arrested after a confrontation on the campus of UCLA, where one of his sons played football. Assault charges are later dropped.
2016: Combs launches a Harlem charter school, the Capital Preparatory School. Also that year, he announces he is donating $1 million to Howard University.
2017: Combs is named the top earner on Forbes' list of the 100 highest-paid celebrities, which says he brought in $130 million in a single year.
2018: Kim Porter, Combs' former girlfriend and the mother of three of his children, dies from pneumonia at age 47.
2022: Combs receives a lifetime honor at the BET Awards.
2023-2025
Sept. 15, 2023: Combs releases 'The Love Album — Off the Grid,' his first solo studio project since 2006's chart-topping 'Press Play.'
Nov. 16, 2023: R&B singer Cassie sues Combs, alleging that during their decade-plus as a couple, he subjected her to abuse, including beatings and rape. A day later, the lawsuit is settled under undisclosed terms. Combs, through his attorney, denies the accusations.
Nov. 23, 2023: Two more women accuse Combs of sexual abuse in lawsuits. Combs' attorneys call the allegations false. Dozens of additional lawsuits follow by women and men who accuse Combs of rape, sexual assault and other attacks. Plaintiffs include singer Dawn Richard, a 'Making the Band' contestant who alleged years of psychological and physical abuse. Combs denies all the allegations.
March 25, 2024: Federal agents search Combs' homes in Los Angeles and Miami Beach, Florida.
May 17, 2024: CNN airs video that shows Combs attacking and beating Cassie in a Los Angeles hotel hallway in 2016. Two days later, Combs posts videos on social media apologizing for the assault.
Sept. 16, 2024: Combs is arrested at his Manhattan hotel. A federal sex trafficking and racketeering indictment unsealed the next day accuses him of using his business empire to coerce women into participating in sexual performances. Combs denies the allegations. His attorney calls it an unjust prosecution of an 'imperfect person.'
May 5, 2025: Jury selection begins for Combs' trial.
May 12, 2025: A jury is selected and testimony begins in Combs' trial.
June 30, 2025: Jury deliberations begin in Combs' trial.
July 2, 2025: The jury convicts Combs of two counts of a prostitution-related offense but acquits him of higher-level charges of racketeering and sex trafficking. The outcome significantly reduces the rap mogul's potential prison sentence, which a judge will determine in the months to come. His lawyers unsuccessfully ask for him to be released on bond in the meantime. Combs is visibly relieved by the verdict, and his lead lawyer calls it 'a victory of all victories.'