From Hip-Hop Icon to Convicted Criminal: The Complete Timeline of Sean 'Diddy' Combs' Rise and Fall

Sean "Diddy" Combs received a prison sentence of four years and two months following his conviction.

For over twenty years, Sean "Diddy" Combs established himself as one of hip-hop's most versatile entrepreneurs, transforming his music production talents into a comprehensive business empire encompassing a record label, fashion brand, television network, partnerships with spirits companies, and a prominent role in reality television.

His career trajectory dramatically shifted when he faced charges of coercing, threatening, and manipulating two former girlfriends into participating in drug-influenced sexual activities with assistance from his associates.

Despite Combs' firm denial of these allegations and his decision to stand trial, the jury ultimately acquitted him of racketeering and sex trafficking charges but found him guilty of transporting individuals across state boundaries for prostitution purposes.

On Friday, he was sentenced to over four years of imprisonment. Below is a chronological overview of significant events throughout his life:

1990: While studying at Howard University, Combs began his music industry journey with an internship at Uptown Records in New York.

December 28, 1991: A tragic incident occurred at a celebrity basketball event organized by Combs and rapper Heavy D, resulting in nine fatalities when thousands of fans attempted to enter a gymnasium at the City College of New York. A subsequent mayoral investigation partially attributed the tragedy to inadequate planning by Combs.

1992: Combs served as one of the executive producers for Mary J. Blige's debut album, "What's the 411?"

1993: Following his dismissal from Uptown, Combs established his own label, Bad Boy, which quickly secured a profitable agreement with Arista Records.

1994: Bad Boy released Notorious B.I.G.'s album "Ready to Die." Two months later, Tupac Shakur survived a shooting in New York and alleged that Combs and Biggie had prior knowledge of the attack, which they denied. Shakur was later fatally shot in Las Vegas in 1996.

1996: Combs was convicted of criminal mischief after allegedly threatening a photographer with a firearm.

1997: Biggie was murdered in Los Angeles. Combs, then known as Puff Daddy, released "I'll Be Missing You" in tribute to his deceased artist.

1998: Combs won two Grammy Awards—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. That same year, his Sean John fashion line was established.

April 16, 1999: Combs and his security personnel were charged with assaulting Interscope Records executive Steve Stoute in his New York office over a dispute regarding a music video. Combs was required to complete an anger management course.

December 27, 1999: Combs was arrested on weapons possession charges after he and his girlfriend at the time, Jennifer Lopez, fled from a nightclub shooting in New York City that left three people wounded. Some witnesses claimed Combs was among those firing weapons in the club. He was subsequently charged with offering his driver $50,000 to claim ownership of the handgun discovered in his vehicle.

March 17, 2001: Combs was acquitted of all charges related to the nightclub incident. His rap protégé, Jamal "Shyne" Barrow, was convicted in connection with the shooting and served nearly nine years in prison. Two weeks following the trial, Combs announced his desire to be known as P. Diddy.

2002: Combs became the producer and star of "Making the Band," a televised talent search program.

February 1, 2004: Combs performed at the Super Bowl halftime show alongside Janet Jackson, Justin Timberlake, and others. One week later, Combs, Nelly, and Murphy Lee received a Grammy for Best Rap Performance by a Duo or Group for "Shake Ya Tailfeather."

April 2004: Combs made his Broadway acting debut in "A Raisin in the Sun."

2005: Combs announced he was changing his stage name to simply Diddy, removing the "P."

March 2008: Combs settled a lawsuit filed by a man who alleged Combs punched him following a post-Oscar celebration outside a Hollywood hotel the previous year. In May, Combs was honored with a star on the Hollywood Walk of Fame.

2015: Combs was arrested after an altercation on UCLA's campus, where one of his sons played football. The assault charges were subsequently dropped.

2016: Combs launched the Capital Preparatory School, a charter school in Harlem. That same year, he announced a $1 million donation to Howard University.

2017: Combs was named the highest earner on Forbes' list of the 100 highest-paid celebrities, reportedly generating $130 million in a single year.

2018: Kim Porter, Combs' former girlfriend and mother of three of his children, died from pneumonia at age 47.

2022: Combs received a lifetime achievement recognition at the BET Awards.

September 15, 2023: Combs released "The Love Album - Off the Grid," his first solo studio project since his chart-topping 2006 album "Press Play."

November 16, 2023: R&B singer Cassie filed a lawsuit against Combs, alleging that during their relationship of more than ten years, he subjected her to abuse, including beatings and rape. The lawsuit was settled under undisclosed terms the following day. Combs denied the accusations.

November 23, 2023: Two additional women accused Combs of sexual abuse in lawsuits. Combs' legal representatives characterized these allegations as false. Dozens of additional lawsuits followed from women and men accusing Combs of rape, sexual assault, and other attacks. Among the plaintiffs was singer Dawn Richard, a contestant from "Making the Band" who alleged years of psychological and physical abuse. Combs denied all allegations.

March 25, 2024: Federal agents conducted searches of Combs' residences in Los Angeles and Miami Beach, Florida.

May 17, 2024: CNN broadcast footage showing Combs attacking and beating Cassie in a Los Angeles hotel hallway in 2016. Two days later, Combs posted videos on social media apologizing for the assault.

September 16, 2024: Combs was arrested at his Manhattan hotel. A federal sex trafficking and racketeering indictment unsealed the next day accused him of utilizing his business empire to coerce women into participating in sexual performances. Combs denied these allegations. His attorney described it as an unjust prosecution of an "imperfect person."

May 5, 2025: Jury selection commenced for Combs' trial.

May 12, 2025: Testimony began in Combs' trial.

June 30, 2025: Jury deliberations started in Combs' trial.

July 2, 2025: The jury convicted Combs of two counts of a prostitution-related offense but acquitted him of more serious charges of racketeering and sex trafficking.

October 3, 2025: A judge sentenced Combs to four years and two months in prison.