The year is 1999. Sean “Diddy” Combs’ “White Parties” are already the talk of the town, despite having started just a year prior. Sitting down with Entertainment Tonight, the rap mogul in the making can’t help but hype up his now-infamous gatherings.
“You’re gonna hear about my parties. They’re going to be shutting them down. They’re probably going to be arresting me doing all types of crazy things just because we want to have a good time, you know?” he declared.
Fast forward to 2024, and that’s exactly what happened — word for word.
Combs — also known as Puffy, Love, and Diddy — is now behind bars, awaiting trial for sex trafficking and racketeering conspiracy charges, among others. With over a 100 sexual assault lawsuits against him and more emerging each day, his once-exclusive parties, which featured alleged “freak-offs,” are now at the centre of a sprawling legal and moral reckoning.
If found guilty in his trial set for May 2025, the man who once ruled the music industry could face anywhere from 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 at the rise — and fall — of Sean “Diddy” Combs.
The Rise of Sean “Diddy” Combs
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. Melvin had ties to convicted drug dealer Frank Lucas.
Raised by his mother, Janice, Combs grew up Roman Catholic and even served as an altar boy. By high school, he’d 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 chase his music dreams.
In 2014, he returned to Howard for an honorary doctorate, but that degree was revoked in 2024 amidst mounting scandals.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 he first showcased his talent for spotting and shaping stars, working closely with Jodeci and Mary J. Blige to refine their styles. This knack for artist development would soon become a cornerstone of his career — and his rise to fame.
Bad Boy Records (1993)
Combs didn’t last long at Uptown Records, getting fired just three years later. He later admitted it was due to his cockiness and oversized ego.
But he didn’t waste time — by 1993, he’d launched Bad Boy Records and secured a deal with Arista Records. One of his first moves was signing a then-unknown rapper named Christopher Wallace — who would soon rise to fame as Notorious B.I.G AKA Biggie Smalls.
“Pretty Wild” Party Lifestyle
By 1994, the release of Biggie’s Ready to Die had 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,” 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 Stern, Usher — who lived with Combs for a year at age 13 — called the early ’90s “pretty wild” and declared that he would never let his own kids around that lifestyle.
East Coast-West Coast Rivalry
By the mid-’90s, the hip-hop world was divided. The East Coast-West Coast rivalry was in full swing, with Tupac Shakur and Suge Knight of Death Row Records taking public shots at Bad Boy Records, Diddy, and Biggie.
What started 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 Las Vegas drive-by on September 7, 1996, followed just months later by Biggie Smalls in a similar shooting in Los Angeles on March 9, 1997.
Both cases remain unsolved, fuelling conspiracy theories that implicate figures like Suge Knight and even Diddy. Notably, the ongoing trial of Tupac’s suspected killer, Duane “Keefe D” Davis — arrested in late 2023 — only points more fingers at Diddy, whom Keefe D accused of ordering a million-dollar hit on Pac.
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 Shyne faced weapons charges, but while Combs was acquitted, Shyne served ten years in prison.
The incident ended Combs’ relationship with Lopez, and years later, Shyne — now a politician — claimed he was made the “fall guy” for his former mentor.
The Fall of Diddy
For over two decades, Diddy remained a cultural force. He managed artists under Bad Boy Records, acted in TV shows, and released music like The Saga Continues and The Love Album: Off the Grid. Along the way, he cycled through stage names, from “Puff Daddy” to “Love.”
But by November 2023, his once-untouchable legacy began to unravel when ex-girlfriend Cassie filed a shocking sexual assault lawsuit. What followed was a cascade of allegations and legal troubles that marked the beginning of his dramatic fall from grace.
Cassie’s Sexual Assault Lawsuit (November 2023)
In November 2023, singer Cassandra “Cassie” Ventura shook the world with a lawsuit against Combs. Their decade-long, on-and-off relationship, which ended in 2018, seemed amicable on the surface — until Cassie accused him of rape, sex trafficking, and years of emotional and physical abuse.
The case was settled within a single day, leading many to wonder what Combs might be hiding behind a massive payout.
Cassie’s claims sparked a wave of similar sexual assault lawsuits, but Combs denied them all, as his once-glittering 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 vacationing at the time, had not addressed any of the lawsuits against him, nor the raid.
Cassie Assault Video Leaked (May 2024)
In May 2024, CNN released shocking footage of Combs physically assaulting his then-girlfriend Cassie in 2016. The grainy hotel surveillance video showed Combs grabbing Cassie 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 address the Cassie situation publicly for the first time, apologising for his actions in a since-deleted Instagram video.
Later, his legal team claimed the Department of Homeland Security leaked sensitive grand jury materials to smear him, but a judge rejected the argument.
SA Lawsuits Keep Pouring In
As the fallout continued, sexual assault lawsuits against Combs kept piling up. New claims seemed to surface every week, with men and women accusing him of assaults going back to the early 2000s. Many alleged they were drugged before being attacked, adding a disturbing pattern to the accusations.
The lawsuits also put a spotlight 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 come to light.
Diddy Arrested (September 2024)
On September 16, 2024, Combs was arrested in New York on charges including racketeering conspiracy and sex trafficking.
100-Plus SA Cases Come In (October 2024)
Even while he was behind bars, the sexual assault lawsuits against Combs kept piling up.On October 1, 2024, over 100 victims came forward with accusations of sexual abuse and exploitation against Combs.
Shockingly, one of the alleged victims was just nine years old when the assault occurred.
Diddy Denied Bail
Combs walked into his bail hearings confident he’d walk out — only to have his request denied not once, not twice, but three times. Now, he’ll be spending the coming months behind bars as he awaits his trial.
