For more than two decades, Sean ‘Diddy’ Combs was one of hip-hop’s most opportunistic entrepreneurs! He turned 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. But U.S. prosecutors say behind the scenes, Combs was coercing and abusing women. He allegedly had assistance from a network of associates who helped silence victims through blackmail and violence.
Combs has pleaded not guilty and denied the allegations. After seven weeks of testimony and arguments from both sides, jury deliberations in his trial began on Monday, June 30. Jurors ended day one without a verdict and will return on Tuesday to continue.
In the meantime, here is a look at the last 20 years of legal troubles that have followed Diddy, including the one time he was acquitted of criminal charges, per the Associated Press.
1990s: Diddy Racked Up Multiple Charges & Convictions
1990: As a student at Howard University, Sean ‘Diddy’ Combs got his start in the music business with an internship at Uptown Records in New York.
Dec. 28, 1991: Diddy and rapper Heavy D were the promoters of a celebrity basketball game where nine people died. The deaths happened when thousands of fans tried to get into a gym at the City College of New York. A mayoral report partially blamed the fatal incident on poor planning by Sean Combs.
1992: Combs is one of the executive producers on ‘What’s the 411?,’ Mary J. Blige‘s debut album.
1993: Diddy starts his label, Bad Boy, and quickly cuts a lucrative deal with Arista Records. This went down after Uptown fired him.
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 Diddy and Biggie of having prior information about the attack. Both of them denied it. Shakur later died 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 dies in Los Angeles. Combs, who by then was Puff Daddy, released ‘I’ll Be Missing You’ in honor of his label’s star rapper.
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, Diddy launched his fashion brand Sean John.
April 16, 1999: Prosecutors charge Sean ‘Diddy’ Combs and his bodyguards 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 Diddy was one of the shooters 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.
#1
2001 — 2008: Sean Combs Acquitted, Sued & Claims Stardom
March 17, 2001: Combs is acquitted of all charges related to the nightclub shooting. One of his rap proteges, Jamal ‘Shyne’ Barrows, is convicted of the shooting and serves nearly nine years in prison. Two weeks after the trial, Combs announces he wants to be known as P. Diddy.
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 from a man who claims Combs punched him after a post-Oscar party outside a Hollywood hotel in 2007. Months later, Combs was honored with a star on the Hollywood Walk of Fame in May.
#2
2015 — 2022: Another Arrest & More Wins For Diddy
2015: Cops arrest Diddy after a confrontation on the campus of UCLA, where one of his sons played football. Assault charges were later dropped.
2016: Combs launched a Harlem charter school, the Capital Preparatory School. That year, he also announced he was 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.
#3
2023 — 2025: Diddy's Luck Runs Out?
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 he subjected her to years of 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 a 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 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 began for Combs’ trial.
May 12, 2025: A jury is selected and testimony begins in Combs’ trial.
June 2025: Testimony ends after seven weeks of testimony from 34 witnesses and arguments from both sides. Defense did not call witnesses, and Diddy did not take the stand. Deliberations in the trial began on June 30.
Associated Press staff contributed to this report.
