The year is 1999. Sean “Daddy” Coombs’ “White Parties” are already the talk of the town despite starting a year ago. sitting with Fun tonightthe rap mogul can’t help but fuel his now infamous collectives.
“You’re going to hear about my parties. They’re going to shut them down. They’re probably going to arrest me doing all kinds of crazy things. Because we want to have a good time, you know?
Fast forward to 2024, and that’s exactly what happened – word for word.
Combs — also known as Puffy, Leo, and Daddy — is now behind bars, awaiting trial on sex trafficking and racketeering conspiracy charges, among others. With more than 100 sexual assault cases against him and more emerging every day, his once-exclusive parties, which allegedly featured “freak-offs,” are now at the center of a wider legal and moral reckoning.
If convicted at his trial in May 2025, the man who once ruled the music industry could face 15 years to life in prison.
But how did Diddy go from hip-hop royalty to facing a mountain of criminal charges? Let’s take a look back at the rise – and fall – of Sean “Daddy” Coombs.
The rise of Sean “Daddy” Coombs
Childhood, Family, and Education
Sean Combs was born on November 4, 1969 in Harlem but grew up in Mount Vernon, New York. Tragedy struck early – his father, Melvin Combs, was killed in a shooting when Sean was just two years old. Malone had a relationship with drug dealer Frank Lucas.
Raised by his mother, Janice, Coombs grew up Roman Catholic and even served as an altar boy. By high school, he had earned the nickname “Puff” for his habit of “huffing and puffing” when frustrated. After graduating from Mount Saint Michael Academy in 1987, he enrolled at Howard University to study business but dropped out after two years to pursue his musical dreams.
In 2014, he returned to Howard for an honorary doctorate, but the degree was revoked in 2024 amid mounting scandals.
Internship at Uptown Records (1990)
In 1990, Combs landed an internship at Uptown Records in New York, where he was mentored by Andre Harrell. It was here that he first demonstrated his talent for finding and modeling stars, working with Giudicki and Mary J. Blige to refine their style. This knack for developing artists would soon become the cornerstone of his career – and his rise to fame.
Bad Boy Records (1993)
Combs didn’t last long at Uptown Records, being fired after just three years. He later admitted that it was because of his indolence and big ego.
But he wasted no time – by 1993, he had launched Bad Boy Records and signed with Arista Records. One of his first moves was to sign a then-unknown rapper named Christopher Wallace – who would soon rise to fame as the infamous BIG AKA Biggie Smalls.
“Pretty wild” party lifestyle
By 1994, the release of Biggie ready to die Made Bad Boy Records a household name. With chart-topping artists like Faith Evans, Total, and Father MC on its roster, the label was unstoppable. Diddy’s production crew, “The Hitmen,” has collaborated with some of the biggest names in music, including Usher, Lil’ Kim, and Mary J. Blige.
But behind the music, Diddy’s party lifestyle was already infamous. In an eyebrow-raising 2016 interview with Howard SternUsher – who lived with Combs for a year when she was 13 – called the early ’90s “pretty wild” and declared that he would never let his children live that lifestyle.
East Coast-West Coast Rivalry.
By the mid-’90s, the hip-hop world was divided. The East Coast and West Coast rivalry was in full swing, with Tupac Shakur and Suge Knight of Death Row Records taking public shots at Bad Boy Records, Daddy and Biggie.
What began as a clash of egos and labels quickly escalated, setting the stage for one of the most infamous and tragic chapters in rap history.
Tupac and Biggie Shooting (1996, 1997)
The late 90s saw hip-hop rocked by tragedy. Tupac Shakur was killed in a drive-by shooting in Las Vegas on September 7, 1996, just months after Biggie Smalls was killed in a similar shooting in Los Angeles on March 9, 1997.
Both cases remain unsolved, fueling conspiracy theories that implicate figures like Suge Knight and even Diddy. Notably, the ongoing trial of Tupac’s suspected killer, Duane “Keefe D” Davis — who was arrested in late 2023 — only points more fingers at Diddy, with Keefe D suing Pac for a million dollars. He was accused of ordering hits.
Jennifer Lopez Club Shooting (1999)
In 1999, Combs and then-girlfriend Jennifer Lopez were enjoying a night out at a Times Square club when shots were fired. Combs and his protégé Shine faced weapons charges, but while Combs was acquitted, Shine spent ten years in prison.
The incident ended Combs’ relationship with Lopez, and years later, Shine – now a politician – claimed he had been made a “fall man” for his former mentor.
The Fall of Daddy
For more than two decades, Diddy remained a cultural force. He managed artists under Bad Boy Records, starred in TV shows, and released music as well. The saga continues. And The Love Album: Off the Grid. Along the way, he cycled through stage names ranging from “Puff Daddy” to “Love.”
But by November 2023, his once-untouchable legacy began to unravel when ex-girlfriend Casey filed a shocking sexual assault lawsuit. What followed was a flurry of accusations and legal troubles that marked his dramatic fall from grace.
Casey’s sexual assault case (November 2023)
In November 2023, singer Cassandra “Casey” Ventura shocked the world by suing Combs. Their decade-long, on-and-off relationship, which ended in 2018, seemed happy on the surface — until Casey accused him of rape, sex trafficking, and years of emotional and physical abuse.
The case was settled in a single day, leading many to wonder what Coombs was hiding behind the massive payout.
Casey’s claims sparked a wave of similar sexual assault lawsuits, but Combs denied them all, as her once-shining reputation began to crumble.
FBI Raid (March 2024)
In March 2024, the FBI raided Combs’ homes in Miami, Los Angeles, and New York as part of a sex-trafficking investigation. Combs, who was on vacation at the time, did not settle any of the charges against him or the raid.
Casey Attack Video Leaked (May 2024)
In May 2024, CNN Combs released shocking footage of himself physically assaulting his then-girlfriend Casey in 2016. Hotel surveillance video shows Combs grabbing Casey by the neck, throwing her to the ground, kicking her, dragging her down a hallway, and throwing a vase at her.
The leak forced Combs to publicly address Casey’s situation for the first time, apologizing for her actions in a since-deleted Instagram video.
Later, his legal team claimed that the Department of Homeland Security leaked sensitive grand jury material to discredit him, but a judge rejected that argument.
SA cases continue.
As the fallout continued, sexual assault lawsuits piled up against Combs. New claims emerge every week, with men and women accusing him of assaults dating back to the early 2000s. Many alleged that they had been drugged before being attacked, adding to a disturbing pattern of allegations.
The litigation also shed light on Combs’ inner circle. So far, R&B singer Aaron Hall and rapper Jay-Z have been mentioned, but fans believe more big names could be on the way.
Diddy Arrested (September 2024)
On September 16, 2024, Combs was arrested in New York on charges of conspiracy to defraud and sex trafficking.
100 plus SA cases reported (October 2024)
Even while he was behind bars, sexual assault charges continued to pile up against Combs. On October 1, 2024, more than 100 victims came forward with allegations of sexual assault and exploitation against Combs.
Shockingly, one of the alleged victims was only nine years old at the time of the attack.
Daddy refused bail.
Combs went into his bail hearings confident he would get out — only to have his request denied not once, not twice, but three times. Now, he will spend the coming months behind bars as he awaits his trial.