30 years before Sean ‘Diddy’ Combs was charged with sex trafficking, he organized a charity event where 9 people were crushed to death. Combs’s long-forgotten past includes three arrests—including for assault and gun possession—two guilty verdicts, and at least 24 lawsuits alleging wrongful death, violence, or property damage. Combs denied wrongdoing in most lawsuits. Fortune’s investigation of Combs’ past included hundreds of document pages and contacted more than 28 individuals.

The minutes ticked by at the “1st Annual Heavy D & Puff Daddy Celebrity Charity Basketball Game.” Attendees who had taken their seats at the City College of New York’s Nat Holman Gymnasium were expecting a jubilant emcee to introduce 50 other celebrities—including some of the biggest names in hip-hop, like Boyz II Men and Run DMC.

But tip-off time came and went. The game never started.

Unbeknownst to those who had arrived early, outside the doors of the arena hundreds of panicked students were being crushed into the bottom of a steep, two-flight stairwell leading down to the gym, a 1992 report by New York deputy mayor of public safety Milton Mollen recounted. Flyers advertising the event littered the steps, leaving them slick and unstable. Hundreds of other fans on the floor above — unaware of the lethal crush below — were still pouring into the building’s lobby from entrances on either side, heaping pressure onto the people trapped on the stairs underneath.

The bottom of the stairwell — only 12 feet by 7 feet wide — was blocked by four metal fire doors. They only opened outward, and were thus held shut by the weight of the crowd in front of them. The crush was so intense that it squeezed the air from the lungs of those inside, Mollen’s report said. Some bodies were pushed upwards, their feet dangling off the ground, one plaintiff in a case against Combs testified in court.

The New York Police Department received its first 911 call at 7:04 p.m. from Benjamin Andrews, one of the attendees, Mollen said. Andrews had just regained consciousness after losing air and becoming overheated in a wave of what he estimated to be 150 people crammed in the stairwell. His message to police over the phone was clear: “People are dying inside of City College.”

According to Mollen’s report, Andrews’ cousin and two of his friends — among nine in total — died from injuries in the stampede that night, December 28, 1991.

A narrow stairway leading to sets of closed doors is littered with flyers. — Hundreds of students and visitors in the Nat Holman Gymnasium for the Dec. 28, 1991, celebrity basketball game were crushed in this stairwell, some slipping on flyers that littered the floor.

When police arrived they found one of the organizers of the event — a little-known 22-year-old hip-hop producer named Sean “Puff Daddy” Combs — “standing there with two women, and all three had money in their hands,” officer Sean Harris testified later in the Manhattan Claims Court.

See also: A timeline of Sean ‘Diddy’ Combs’ long-forgotten legal track record.

Combs said in multiple testimonies, including as a witness in a 1998 trial, that he was immersed in the melee trying to help pull individuals from the stairwell.

But Mollen’s report named Combs as one of the people responsible for the deaths, due to his failure to provide enough security personnel on the day. The surviving families of the victims sued Combs and others for $500 million. A court later held Combs — and Heavy D — 50% liable for the stampede. Combs settled eight of nine wrongful death suits, paying about $600,000 in settlements.

Now 55, Combs has been held in a Brooklyn jail since September, where he awaits trial on federal charges of racketeering, sex trafficking, and transportation to engage in prostitution. Combs has pleaded not guilty. He was named as a defendant in 30 additional civil suits. One of them, filed in December by a “Jane Doe,” alleges that on the night of the stampede Combs gave her what she was told was Coca-Cola, which made her feel woozy. Combs sexually assaulted her in his dressing room minutes before the event began, she alleges.

Combs has denied the allegations of sexual assault and trafficking. His legal team did not respond to Fortune’s specific inquiries about the City College stampede or previous litigation against Combs, but they did offer a statement regarding the sexual assault allegation the night of the stampede.

“Mr. Combs cannot respond to every new publicity stunt, even in response to claims that are facially ridiculous or demonstrably false,” they said. “Mr. Combs and his legal team have full confidence in the facts and the integrity of the judicial process. In court, the truth will prevail that Mr. Combs never sexually assaulted or trafficked anyone—man or woman, adult or minor.”

Tony Buzbee, a personal injury lawyer representing the anonymous plaintiff and dozens of others alleging Combs sexually assaulted them, predicts up to 300 civil cases could be filed against Combs based on 3,000 calls he said he and his team received from prospective clients.

But decades before he would face these mounting lawsuits, Combs was no stranger to sitting in courtrooms. The aftermath of the City College stampede would mark the beginning of Combs’s now long-forgotten past, which includes three arrests—including for assault and gun possession—two guilty verdicts, and at least 24 lawsuits alleging wrongful death, violence, threats, or damage to personal property. Combs denied wrongdoing in most of these lawsuits and settled at least 11 of them.

Fortune examined hundreds of document pages, visited the Nat Holman Gymnasium, and reached out to more than 28 individuals involved in the stampede or its aftermath, and within Combs’ orbit to chart the still-rippling wake Combs left on his way to become one of hip-hop’s most celebrated producers and an entrepreneur at one point worth $1 billion.

“We are disappointed with the decision to pursue what we believe is an unjust prosecution of Mr. Combs by the U.S. Attorney’s Office. Sean ‘Diddy’ Combs is a music icon, self-made entrepreneur, loving family man, and proven philanthropist who has spent the last 30 years building an empire, adoring his children, and working to uplift the Black community. He is an imperfect person, but he is not a criminal,” Sean Combs’ attorney Marc Agnifilo said in September following Combs’ arrest on the three felony charges. Combs’ legal team offered the same statement to Fortune for a related story in December 2024.

“To his credit Mr. Combs has been nothing but cooperative with this investigation and he voluntarily relocated to New York last week in anticipation of these charges,” Agnifilo said. “Please reserve your judgment until you have all the facts. These are the acts of an innocent man with nothing to hide, and he looks forward to clearing his name in court.”

The ‘kingmaker’

In the last week of December 1991, “Forever My Lady” by the heartthrob R&B group Jodeci was spending its 10th week on the Billboard Hot 100. Combs was working at the label that produced the record—Andre Harrell’s Uptown Records. He had been hired as an intern the year before, having dropped out of Howard University, where he studied business, that same year.

Hip-hop was still only at the beginning of its journey into the heart of mainstream music in the 1990s. Combs was there to cash in on the burgeoning genre and usher in the era of hip-hop that dominates music sales today. In 1992, Mary J. Blige’s debut album “What’s the 411?”, which was produced by Combs at Uptown, reached triple-platinum status, selling 3.5 million records.

“I do remember his energy always being that of, ‘We’re gonna win,’” Blige said in the 2017 documentary Can’t Stop Won’t Stop: A Bad Boy Story.

akua naru, assistant professor of music at the University of California Santa Cruz (whose name is intentionally stylized in all lower-case letters), called Combs a “kingmaker” in an interview with Fortune, crediting him for a decades-spanning lineage of R&B and hip-hop superstars from Usher, who lived with Combs in the 1990s shortly after signing with LaFace records; to Justin Bieber, whom Usher helped bring to the spotlight in 2008.

Combs’ tough upbringing was baked into his street-cred backstory. He was born in Harlem and raised by a single mother after his father was murdered. He became known as “Puffy” at 14 and “Puff Daddy” by age 17 due to his demeanor on the football field. “It was a joke,” Combs said in a 1997 deposition as part of a case regarding the City College stampede. “Just about us playing a football game, and when I made a tackle, he said I ‘puffed up.’”

“Whenever I got mad as a kid, I used to always huff and puff,” Combs said in a 1998 edition of Jet magazine. “I had a temper.”

The “Puffy” persona was both a blessing and a curse for the young entrepreneur. Combs was famously fired from Uptown Records in July 1993 over mounting tensions between him and Uptown founder Harrell. Combs told Oprah Winfrey in a 2006 interview he was “passionate” at the time and “didn’t understand workplace protocol or workplace politics.”

Andre Harrell and Sean Combs sitting at a table with a gingham tablecloth, looking at the camera. — Uptown Records founder Andre Harrell (left) and Sean Combs at Lifebeat’s Urban Aid benefit concert at Madison Square Garden on Oct. 5, 1995. Harrell would serve as a mentor to Combs, but fired him from the label in 1993.

A former employee remembered events differently. “He was always in a hurry, and you knew when he came in, it was like, all the fun would end,” Pam Lewis-Rudden, Combs’ first assistant at Uptown Records, told Fortune. “He was always really pissed off about something, and he’d blow in, get everybody all riled up, and leave. A couple months in, he started calling everybody a ‘bitch.’ ‘All bitches to the meeting room …’”

Harrell, who served as a mentor to Combs and died in 2020, said his decision to fire Combs came from a desire to maximize the young producer’s potential. Harrell continued to keep Combs on Uptown’s payroll even after firing him and planned to do so until Combs landed on his feet elsewhere, he told the Wall Street Journal in 2014.

“I didn’t do it to hurt him,” Harrell said. “But I knew it was time for him to grow.”

Later that year, Combs founded Bad Boy Records and signed Mary J. Blige and the Notorious B.I.G. By the late 1990s, Bad Boy was bringing in $130 million in annual revenue.

‘I had blacked out from the pressure of the crowd’

Combs’ tenure at Uptown would forever be marred by the City College stampede. Combs said he became inspired to host a charity basketball game after Los Angeles Lakers point guard and five-time NBA champion Earvin “Magic” Johnson’s November 1991 announcement he was living with HIV, according to the 1997 testimony in a personal injury suit in which Combs was named a defendant. A portion of the event’s proceeds would go to an organization raising awareness and resources for HIV/AIDS, which at the time was an almost universally fatal disease.

Combs enlisted Tara Geter, a one-time member of R&B group the Gyrlz, which released a record with Uptown, to take care of the event’s logistics, according to the deputy mayor’s 1992 report. While Combs was on the phone in his office, Geter arrived to deliver the contract from one of City College’s student government bodies for Combs to sign. Geter left the contract in an envelope on Combs’ desk, which he apparently spent little time looking over.

“Mr. Combs stated that he read the contract in a cursory manner but that he never read the contract in detail prior to the event,” Mollen wrote in his report. “And he acknowledged that he never obtained insurance for the event.”

Infographic shows how the deadly crowd crush unfolded at the Nat Holman gymnasium in December, 1991

It was a sign of more inattentiveness to come. The event was advertised as a fundraiser for an HIV/AIDS resource organization, which would set up a table at the game to disperse condoms and educational materials. But the event organizers never successfully signed up a charity to do it, meaning the money they raised for the event had nowhere to go. Geter initially reached out to several HIV/AIDS advocacy groups ahead of the event, one of whom referred her to the New York City Health Department’s AIDS Education and Community Outreach Unit. The Health Department told Geter they did not accept donation money but could host a table at the event.

Geter was unable to close the loop with the Health Department, having left New York for a week to attend a family funeral ahead of the basketball game. She left a voicemail with the agency asking a staff member to confirm with her or Combs that a representative would be present at the event. Having assumed Geter had taken care of the charity component of the event, Combs had no further contact with the city’s health department office, according to Mollen’s report.

“Although Mr. Combs may have intended to provide a portion to an AIDS education organization, it was inappropriate to have the flyers for the game printed before specific and concrete arrangements were made in this regard,” Mollen said.

The $24,581 raised at the event, minus expenses, was given to the New York City Law Department, which put the funds in an escrow account.

The hip-hop producer was also contractually obligated to provide security for the event beyond what City College planned to provide, so he enlisted help from local security firm X-Men Security Inc. and suggested about 15 to 20 guards occupy the outside of the gym.

“I don’t remember how we got to the staircase, because it was so many people around me, it wasn’t like I was going with the crowd, I was being pushed.”
Michael Childs, plaintiff and witness at the City College stampede

Combs said it was the college’s responsibility to make sure all of the security measures were coordinated. Milton David, part of the City College Security Office, saw a flyer for the event the day before—and “panicked” upon seeing the list of guests, who would surely draw a huge crowd, per Mollen’s report. The morning of the event—and his day off—David came into the office and was able to put together an additional 17 guards to cover the event. David also left a message for the 26th precinct police before leaving for the day.

Combs had spent most of his energy promoting the event, telling the head of the CCNY student government there were 1,500 advanced tickets sold, and said he sold an additional 500 at the door, according to Mollen. However, on the day of the game, about 5,000 people attempted to enter the event, according to multiple reports at the time. As an experienced promoter, Combs should have put more effort into coordinating security and only allowing ticket-holders into a gymnasium with a 2,730 person capacity, Mollen said in his report.

The outside of a gymnasium building has people standing around outside and is blocked off with police barricades. — Police stood outside the City College of New York building housing the Nat Holman Gymnasium. The gym had a capacity of 2,370 people but reportedly had 5,000 try to enter the night of the stampede.

The line was orderly at 4:00 p.m. until the celebrity participants began to arrive 90 minutes later, at which point ticket holders began to get restless, toppling barricades in front of the building and pressing up against the gym’s glass windows. When non-ticket holders began pouring into the lobby, the advance ticket holders pushed forward, warping and cracking the glass windows. Security and police tried to hold the crowd back and called in reinforcements. But people had already started filling the stairwell leading to the gym on the floor below.

“I don’t remember how we got to the staircase, because it was so many people around me, it wasn’t like I was going with the crowd, I was being pushed,” plaintiff Michael Childs, who attended the event with his sister and her friend, said in a deposition. “So next thing I know we was going down some stairs.”

Childs recalls being separated from his friends and not seeing any police, security, or medical professionals as he was pushed into the stairwell. He said that as he stumbled down two flights of stairs, his feet weren’t touching the ground. It was one of the last things he remembered before passing out.

“I had blacked out from the pressure of the crowd and I woke up in the hospital,” he said.

Eight people died at the scene. A ninth died in hospital a few days after. Their names were Darren Anthony Brown, Yul Clayton Dargan, Laytesha Krishon Heard, Dawn Shantel McCaine, Leonard Anthony Nelson, Jr., Charise Ann Noel, Jabaal Rainey, Dirk Swain, and Sonya Michelle Williams.

According to chief medical examiner Dr. Charles Hirsh, all nine fatalities were a result of asphyxia and excessive compression of the chest, Mollen’s report said. Twenty-nine others suffered injuries.

Emergency officials carry a gurney into an ambulance. — The City College stampede ultimately claimed nine lives and resulted in at least two dozen people getting injured.

According to Mollen, Combs was in the lobby as the crowd swelled at 6:50 p.m., five minutes before the stampede. He and an associate, Jessica Rosenbaum, wanted to secure the money from the ticket table as people poured into the building. Rosenbaum cradled two cashier trays filled with cash and descended into the gym, followed by one of Combs’ bodyguards and four others working at the ticket table. Combs stayed in the lobby.

Combs testified in 1998 as a witness to the Manhattan Court of Claims he was at the bottom of the stairs as the stampede began, helping those at the gymnasium door pull unconscious bodies from the stairwell

But accounts from others of Combs grabbing the cash during the stampede cast doubt on that story, according to a ruling by Judge Louis Benza. “This revelation places a strain on the credibility of Combs’ testimony that he was caught up in the melee and attempted to help the people who were trapped in the stairwell,” he wrote.

30 years of violence and litigation

The lawsuits Combs faced as a result of the stampede would mark the beginning of a slew of litigation against him spanning more than 30 years.

In 1995, Combs was ordered to pay $2.45 million in damages to Cedrick Bobby Lemon, who claims he attended a Mary J. Blige concert and was assaulted by two of Blige’s bodyguards, hired by Combs. Lemon, 25, was hospitalized and sustained fractures to his right ankle, which required three surgeries inserting seven permanent screws there. A judge initially ruled Lemon would be awarded damages by default after Combs did not show up to court, but the court also found Lemon did not submit the necessary documents to receive a default judgement, and the lawsuit was overturned.

Four years later, Combs was arrested and charged with second-degree assault and criminal mischief for beating record executive Steven Stoute. Stoute said Combs and two bodyguards hit him with a bottle of champagne, a chair, and a telephone. The charges were reduced to harassment following Combs’ public apology, and the two reportedly reached a $500,000 settlement. Combs took a one-day court-ordered anger management class.

In 2004, Damien Vazquez, a former driver for Bad Boy Records, alleged Combs accused him of stealing a Grammy award and enlisting a police officer to arrest Vazquez on charges of larceny and possession of stolen property. Vazquez, who is diabetic, allegedly passed out in his jail cell after being refused food and was sent to the emergency room. The case was dismissed after a judge found insufficient evidence, and Vazquez chose not to refile the case.

One of Combs’ most high-profile run-ins with the law involved then-girlfriend Jennifer Lopez, his bodyguard Anthony “Wolf” Jones, and Jamal “Shyne” Barrow, an up-and-coming rapper and Combs’ protege, at Club New York in 1999. An argument in the club resulted in a shooting that injured three people. Combs, Lopez, and Jones left the club in Combs’ Lincoln Navigator, in which New York police later found a stolen gun. Combs was indicted on gun possession charges and allegedly bribed his chauffeur Wardel Fenderson to take responsibility for the firearm. Prosecutors alleged the occupants of Combs’ car tried to open a secret compartment to hide two firearms as police chased the vehicle. Combs faced 15 years in prison if found guilty, but he was acquitted. Instead, Barrow was convicted of first-degree assault, reckless endangerment, and weapons possession, and served a nearly nine-year prison sentence.

“Gangsters like Al Capone and even the fictional gangsters are all things that, as a culture, we consume with delight. We root for these kinds of characters.”
A.D. Carson, associate professor of hip-hop at the University of Virginia

The cases extended beyond clubs and parking lots. Combs signed a book deal with Random House in 1998, receiving a $300,000 advance to write a memoir. In a 2005 lawsuit, Random House alleged Combs did not turn in a manuscript or pay back the advance. Writer Mikal Gilmore, who was hired to assist Combs with the book, said he had little interaction with the producer after the contract was inked. Combs settled the case with Random House, which scrapped Combs’ book.

In 2011, Combs settled an age discrimination lawsuit filed by former Bad Boy senior vice president Francesca Spero, who alleged Combs fired her after she underwent major hip surgery and disclosed to another executive she had undergone treatment for drug dependency.

‘Bad Boy 4 life’

In 2001, Combs owned his reputation with a hit song titled “Bad Boy 4 Life.” The “Bad Boy” brand and the lawsuits became part of the Combs’ mythology, according to A.D. Carson, rapper and associate professor of hip-hop at the University of Virginia. Combs’ “Bad Boy” Record and “Puff Daddy” moniker indicated a level of self-awareness, Carson said. His cruelness—well-documented on MTV’s “Making the Band” reality TV show, where he famously asked members of Da Band to walk three hours from Manhattan to Brooklyn to retrieve a slice of cheesecake—was seen as a form of authenticity that American audiences celebrated.

“Gangsters like Al Capone and even the fictional gangsters are all things that, as a culture, we consume with delight,” Carson said. “We root for these kinds of characters.”

Though Combs’ proclivity for violence and manipulation was well-known, his reputation has been laundered in the years since. Even Fortune polished Combs’s legacy by casting him as a shrewd entrepreneur, in a 2014 profile on his venture with alcohol conglomerate Diageo.

“With Ciroc, people may have thought that [the vodka] was for African Americans,” Combs told Fortune at the time. “People wanted to put it in a box. So the biggest lesson I learned is that I had to work harder to overcome those perceptions and create a wonderful product regardless of my color, regardless of my celebrity. The reality is I have to work harder than other brands to do that.”

These two halves of Combs—the temperamental producer and the savvy businessman—are not diametrically opposed, Carson argued. Instead, they contribute to a narrative that Combs was willing to bend the rules and step on others in order to advance professionally.

“The thing that is happening in music, particularly in what folks call or understand to be Black music, follows the same kind of trajectory that people associate with the so-called American Dream—that rags-to-riches, ‘I worked really hard’, or ‘I literally started as an intern, and now I own the building’ kind of story,” Carson said.

“Diddy became synonymous with the kind of mythos of great American men that this country loves to produce and reproduce,” he added.

‘To the City College deceased, may you rest in peace’

In the week following the stampede, Combs faced reporters with a bowed head and shaking voice, The New York Times reported in January 1992. “In addition to sponsoring a profitable event,” Combs told a bombardment of press in the salon room of the Plaza Hotel in Midtown, “my dream for this evening was to bring a positive program to my people, to people of my age and to people of my community.”

But as time went on, Combs’ relationship with the stampede became ambivalent. In 1997, Combs’ album No Way Out debuted at No. 1 on the Billboard 100, selling 561,000 copies in its first week. Deep into the album on the song “Pain,” Combs appears to both acknowledge the harm of the City College tragedy while shirking responsibility for it.

“To the City College deceased, may you rest in peace / To the families, I never meant to cause no pain / I know the truth, but if you want, then I shoulder the blame,” Combs says.

The following year, Judge Benza would rule that indeed Combs—and Heavy D—were 50% liable for the stampede and the lack of coordinated security. Also held liable was City University of New York, the defendant in the Court of Claims case and the university system of which CCNY is a part.

Sean Combs sits with his head in his hand as Heavy D stands at a podium with his head down. — Sean Combs and Dwight “Heavy D” Myers at a news conference five days after the City College stampede. New York Court of Claims Judge Louis Benza would ultimately rule the two of them 50% responsible for the tragedy.

Though Combs said “City College is something I deal with every day of my life” after a 1998 court appearance, his career flourished. He would earn five Grammy nominations for No Way Out, and the album would nab the award for best rap album. But if Combs was grappling with his fame and his costly mistakes, so, too, were the stampede victims’ families.

“The Grammys? He deserves them. The people love him. He’s talented. I don’t have any malice in my heart for Sean,” plaintiff Barbara Swain, who lost her son in the stampede, told the New York Daily News in 1998. “Sean’s era is now. He is just a young man who could have been my son.”

Combs’ dominance of hip-hop appears to be at an end. His $300 million net worth is diminishing in real time. Music professor naru warned of trying to decipher what the indictment and mounting lawsuits mean for Combs’ legacy. “Who cares at this point?” she said. “What matters, really, for me, is that victims are getting the support—that those who are violated whether sexually or physically, otherwise get the support that they need. You know, that’s the most important.”

Even as Swain praised Combs in one breath more than 25 years ago, in another, she wished he would take more accountability: “I want Sean to step up to the plate and say, ‘I made a mistake. I shouldn’t have done this.’”

30 years before Sean ‘Diddy’ Combs faced sex trafficking charges, he organized a celebrity basketball game where 9 people were killed in a stampede