Sean "Diddy" Combs, the famed multi-hyphenate rap artist, music producer, record label owner and fashion mogul, has lived a tumultuous life.
Born in New York City in 1969, Combs attended Howard University for two years before leaving to embark on a career in music, one that earned him 14 Grammy nominations, including three wins, for his gold- and platinum-selling solo studio albums. He parlayed his musical notoriety into a successful clothing line as well as other business ventures, at one time boasting an estimated net worth in excess of $1 billion.
Combs also enjoyed success as an actor, both on Broadway and in a number of roles on both the big and small screens, in the process cementing his position as a powerful figure in the music and entertainment industries.
But that life also included significant legal challenges on more than one occasion, including a deadly stampede that occurred at a music event that he promoted early in his career, a nightclub shooting, and sexual misconduct accusations from numerous people that preceded a criminal investigation and resulted in multiple indictments. Combs has denied all allegations.
With Combs now on trial for alleged racketeering, sex trafficking and transportation to engage in prostitution, here's a timeline of several of the ups and downs of Sean "Diddy" Combs.
Combs began his career in music in the early 1990s as an intern at Uptown Records, the legendary New York City R&B and hip-hop record label founded by Andre Harrell, who's widely credited with giving Diddy his start in music.
Combs was one of the co-promoters of a 1991 charity basketball game held at City College of New York. The event, which took place in the college's gymnasium, was oversold, resulting in a packed crowd that stampeded, with many patrons crushed in the throng. Nine people died and 29 were injured.
No criminal charges were ever filed for the stampede, but civil lawsuits from victims and their families went on for years against Diddy, co-promoter rapper Heavy D, the City College of New York and other defendants.
At the time, Combs’ lawyers argued that he was not responsible for security. A judge in one lawsuit filed by four victims found that Diddy, Heavy D, and the college were equally responsible for the injuries and deaths, according to the New York Times.
''City College is something I deal with every day of my life,'' Combs told The New York Times outside court in 1998, after testifying in one of the suits. ''But the things that I deal with can in no way measure up to the pain that the families deal with. I just pray for the families and pray for the children who lost their lives every day.'' All of the civil suits tied to the incident reached out-of-court settlements, according to CBS News.
''City College is something I deal with every day of my life,'' Combs told The New York Times outside court in 1998, after testifying in one of the suits. ''But the things that I deal with can in no way measure up to the pain that the families deal with. I just pray for the families and pray for the children who lost their lives every day.''
Jury selection continues in Sean ‘Diddy’ Combs trial
After being fired from Uptown Records in 1993, Combs founded his own record label, Bad Boy Records.
“Andre Harrell fired me and so that adversity kind of pushed me into my Bad Boy purpose,” Combs said in an interview clip posted to social media in 2023. “As Andre said, he didn’t fire me to hurt me – he fired me to make me rich.”
And rich Combs would become. The music mogul’s new label signed rapper Notorious B.I.G., then one of the most prominent names in hip-hop, and over the years would eventually sign several other topline acts like Faith Evans, Cassie Ventura, Machine Gun Kelly, Pitbull and, more recently, Janelle Monáe.
Combs, who then performed as Puff Daddy, released his 1997 debut album, “No Way Out,” on his Bad Boy Records label. According to Diddy, the album was heavily inspired by the March 9, 1997 shooting death of Diddy’s close confidant and Bad Boy artist Notorious B.I.G.
The album included 18 tracks and featured some of the biggest rap stars of the time, including Notorious B.I.G., posthumously, Jay-Z and Busta Rhymes.
"No Way Out" went on to win the Grammy for best rap album at the 40th annual Grammy Awards the following year. Combs also took home a Grammy for best rap performance by a duo or group for “I’ll Be Missing You,” another track off the album, featuring Faith Evans and 112.
In the spring of 1998, Combs expanded his business interests with the launch of his successful Sean John men's fashion brand focusing on sportswear.
Combs was arrested in 1999 for his alleged involvement in the beating of former Interscope record executive Steve Stoute in New York. Combs pleaded guilty to the lesser charge of harassment, and was ordered to attend a one day anger management class.
Combs, his then-girlfriend Jennifer Lopez and rapper Shyne were taken into police custody after a Dec. 27, 1999, shooting at a Manhattan nightclub. Lopez was never charged with a crime.
Diddy was acquitted of all charges in connection with the shooting. A jury cleared Combs of allegations he fired a weapon during the dispute that wounded three bystanders. Shyne was convicted of numerous related crimes and sentenced to prison.
2004 marked a momentous year in Combs' life. He began the year by performing at the Super Bowl XXXVIII halftime show as part of a star-studded group of headliners that included Nelly, Kid Rock and Jessica Simpson, as well as Janet Jackson and Justin Timberlake, whose duet performance resulted in the notorious "wardrobe malfunction" controversy.
Shortly afterward, Combs continued his hot streak with a Grammy win for best rap performance by a duo or group for “Shake Ya Tailfeather” with Nelly and Murphy Lee, from the soundtrack to the film "Bad Boys II."
Combs also made his Broadway acting debut in April of the same year in the revival of Lorraine Hansberry’s classic drama “A Raisin in the Sun,” starring alongside Phylicia Rashad and Audra McDonald. The trio later starred in a 2008 television adaptation of the play.
Combs was sued for assault and battery and general negligence in March of 2007 after an alleged fight that broke out at the Roosevelt Hotel in Los Angeles. According to the lawsuit, Combs "intentionally, willfully, knowingly and unlawfully battered" the plaintiff, pushed the plaintiff's girlfriend and spit on another female involved. Combs denied the allegation and the case was ultimately dismissed after a settlement was reached in May of 2008.
In 2015, Combs was arrested on felony charges after he allegedly assaulted and threatened a coach for the UCLA football team, for which Combs’ son was a defensive back, with a kettlebell weight.
After an investigation, the Los Angeles County District Attorney's Office announced they were dropping all charges against Combs.
Diddy trial: This is everything you need to knowCombs gave back to his birth city in 2016 when he helped launch the Capital Preparatory Harlem Charter School.
The school, which had an inaugural class of 160 students in grades six and seven, was opened to “provide historically disadvantaged students with the college and career readiness skills needed to become responsible and engaged citizens for social justice,” according to the school’s mission statement.
On November 16, 2023, Combs’ ex-girlfriend Cassie Ventura filed a lawsuit accusing Combs of physical, sexual and emotional abuse during their relationship. Combs denied the allegations. The very next day after the suit was filed, Combs and Ventura settled the lawsuit, with Combs admitting no wrongdoing and both parties saying the matter had been resolved “amicably.”
Since Combs' and Ventura's settlement, the rapper has faced a series of civil lawsuits from multiple people, alleging behavior including several instances of drugging, raping and sexually assaulting alleged victims at parties and social gatherings. Combs has denied all allegations and said he never sexually assaulted anyone and that any sexual relations were consensual. Several suits have been withdrawn or dismissed while others are still proceeding.
In March 2024, four months after the Ventura lawsuit was settled, federal agents with Homeland Security Investigations raided Combs’ homes in Los Angeles and Miami as part of an "ongoing investigation."
"Earlier today, Homeland Security Investigations (HSI) New York executed law enforcement actions as part of an ongoing investigation, with assistance from HSI Los Angeles, HSI Miami, and our local law enforcement partners," a spokesperson for Homeland Security Investigations said in a statement. "We will provide further information as it becomes available."
Law enforcement sources familiar with the matter said at the time that the searches were being conducted as part of a federal investigation led by the Southern District of New York into alleged human trafficking.
On September 12, 2024, a federal indictment was unsealed charging Combs with multiple counts of racketeering, sex trafficking and transportation to engage prostitution.
Federal prosecutors said at the time that Combs "abused, threatened, and coerced women and others around him to fulfill his sexual desires, protect his reputation, and conceal his conduct" from 2008 to the time of the indictment. Some of the charges echoed many allegations contained in multiple civil complaints filed against Combs since 2023.
Combs was arrested four days later in New York City and pleaded not guilty in court on Sept. 17. He was denied bail and held in federal custody.
In January 2025, prosecutors filed a superseding indictment that alleged Combs "abused, threatened and coerced women and others around him to fulfill his sexual desires" over a longer period of time than alleged in the initial indictment.
The new indictment did not include additional charges against Combs, but added additional details and two new alleged sex trafficking victims. Combs pleaded not guilty to the new charges.
Yet another superseding indictment was filed in March 2025 that added an allegation that Combs forced employees to work long hours under threat of physical and reputational harm. Combs again pleaded not guilty to the additional charges.
Finally, in April 2025, a third superseding indictment added two additional charges to those Combs already faced: one charge of sex trafficking and another charge of transportation to engage in prostitution.
Federal prosecutors also updated the language of the racketeering conspiracy charge Combs faces, specifying that he " kidnapped and carried and displayed a firearm to female victim, and that the defendant dangled a female victim over an apartment balcony."
In a statement to ABC News in March, Combs' attorney Marc Agnifilo said, “Mr. Combs has said it before and will say it again: he vehemently denies the accusations made by the SDNY. He looks forward to his day in court when it will become clear that he has never forced anyone to engage in sexual acts against their will. Many former employees stand by his side, prepared to attest to the dedication, hard work, and inspiration they experienced while helping build groundbreaking, award-winning businesses.”
The trial is officially underway as jury selection and opening statements will come this week.
ABC News Aaron Katersky contributed to this report.
