The Shady Side Of Diddy

Sean Combs built a rap empire over the last three decades — one that could very well crumble if he is found guilty of the numerous allegations of sexual assault lodged against him in recent times. Combs, who is referred to by various monikers like Diddy, P. Diddy, and Puff Daddy, rose to fame in the 90s after starting his record label Bad Boy Entertainment. Not only did he launch his own successful solo career, but he kickstarted the careers of legends such as Notorious B.I.G., Mase, and Faith Evans, and worked with R&B superstars like Mary J. Blige and Usher throughout his lengthy career. 

But the man who liked to think of himself as "The King of New York" has a dark history hidden behind his flashy fortune. Diddy has been involved in various rap beefs (some that have turned deadly) since the start of his empire, but he has always managed to escape unscathed despite mounting evidence against him. The rapper's billion-dollar business now stands in a cloud of uncertainty as federal agents have already raided his mansions as part of a potential federal sex trafficking case. Combs' sketchy behavior is catching up to him — with the entrepreneur's whereabouts unknown amidst the investigation. We're breaking down the shady side of Diddy — from rap extraordinaire to man on the run.

Before Sean Combs became a household name, he was earning his way into the industry as a rap promoter. His initial rise to fame included an immense tragedy, however, when Combs was at the center of a celebrity basketball event that turned into a deadly stampede.

In late December of 1991, Diddy organized the charity game at City College in Harlem, New York which featured artists like Boyz II Men, Run-DMC, and Jodeci. Due to poor crowd management and a lack of security, the event ended in mayhem, with a massive crowd attempting to rush into the stadium. Up to 5,000 people showed up to the event with a capacity of 2,730, resulting in a crowd surge that killed nine individuals and left 29 more injured.

The tragedy resulted in a civil lawsuit against City College brought by several of the victims' families, with Diddy testifying on the stand. According to court documents published by the Associated Press (via The New York Times), the rapper remembered that he "started seeing different young ladies getting squished" adding, "You could see panic on everybody's face.” Combs eventually settled several lawsuits brought against him by families involved in the chaos. The memory haunts him, however, with the producer admitting on the stand in 1998, "City College is something I deal with every day of my life. But the things that I deal with can in no way measure up to the pain that the families deal with."

Death Row Records and Bad Boy Entertainment were once rivals in an East Coast vs. West Coast feud that holds a deadly place in rap history. The story began on good terms, as Sean Combs was previously friends with Death Row Records co-founder Marion 'Suge' Knight. A violent fight outside an Atlanta nightclub changed all that, however, when an argument with members of the Bad Boy label turned fatal and Knight's security guard, Jake Robles, was killed. 

Per the The Los Angeles Times, then-Fulton County deputy sheriff Chris Howard escorted members of Bad Boy outside the Platinum City Club and was attempting to escort Knight and his entourage to their cars when the shooting occurred. "[Knight's] partner was just about ready to get into the limo when all of a sudden Puffy's guys came from around the corner ... and one of them had a gun," Howard told the publication. He pursued the armed man, who handed the gun to his associate who then shot Robles several times. Robles was taken to an Atlanta hospital and succumbed to his injuries weeks later.

The shooter's weapon was never recovered from the scene, but an informant told authorities that the man responsible for Robles' death was Diddy's then-bodyguard Anthony 'Wolf' Jones. Jones' attorney denied his client's involvement in the incident at the time, as did an attorney for Combs. Despite Howards' claim that the shooter was from Diddy's label, Atlanta police never investigated the Bad Boy founder or his entourage about their involvement.

Sean Combs was involved in yet another media debacle in the 90s when he got into a violent fight with music executive Sean Stoutes. The issue was sparked after Stoutes, who was Nas' then-manager, accidentally sent the wrong version of Nas and Combs' "Hate Me Now" music video to premiere on MTV in 1999. In the first version, Combs was depicted as Jesus Christ on the cross, but he had ordered those scenes be cut out.

Stoute told MTV that upon discovering the mix-up, Combs and two of his business partners stormed into his office and beat him up, leaving him with a broken jaw and arm. The music executive was charged with second-degree assault and criminal mischief at the time. "One minute I'm in the middle of a meeting," he told the Los Angeles Times after the incident, "and the next minute I'm down on the floor and Puffy and his guys are kicking and pounding me. One of them picks up a chair and throws it at me. Then Puffy throws my desk over and they just walk out like nothing happened."

Combs later apologized for the fiasco, telling MTV, "I can say this, his jaw was never broken as was reported, his arm was never broken. I mean, I never hit him with a bottle or a chair or nothing like that ... But I can't get into the play-by-play details, but I can say this: I'm totally wrong, and I really feel sorry about it."

Diddy was involved in a highly controversial gun trial that led to a shocking acquittal at the turn of the century. In December of 1999, Sean Combs was partying with his then-girlfriend Jennifer Lopez at a nightclub in Manhattan celebrating new music by his former-signee Shyne, (real name Jamal Barrow). According to New York magazine, Puff Daddy accidentally bumped into a man named Matthew Allen, spilling the drink in his hand and leading to a scuffle. A man from Allen's entourage reportedly threw a stack of money in Combs' face, which led to all the men drawing their guns.

According to Rolling Stone, Shyne shot three times into the nightclub, striking three individuals. Diddy was charged with four weapons charges as well as for bribing his driver to say that he owned the guns. The case ultimately went to trial, but a convincing argument from lawyer Johnnie Cochran led to Combs being acquitted of all charges, despite witnessing testifying that they saw him fire his gun. Shyne, however, was sentenced to 10 years behind bars after being found guilty of five of eight charges against him. 

The king of scuffle was at it again in 2013 when tabloids got wind of yet another altercation in which Sean Combs was involved. Puff Daddy got to puffing his chest at the VMAs that year after hearing Kendrick Lamar's feature on Big Sean's track "Control." In the track, Lamar takes shots at various rappers and even dubs himself "The King of New York," a title Diddy had been known to call himself. 

As reported by Complex, a reportedly intoxicated Diddy allegedly confronted the rapper over the song, and may or may not have poured a drink on his head. An argument ensued, J. Cole reportedly intervened by putting his hands on Diddy, and a tussle broke out between Diddy and Lamar's entourages. The fight was ultimately broken up, and the rest is history. However history can be interpreted in different ways, and one witness told Page Six at the time that it was J. Cole who was hurling insults at Puff Daddy and his then-girlfriend Cassie. 

While we may never know the truth behind the VMA fracas, J. Cole has since released music re-hashing the incident. In his track "Let Go My Hand," he raps: "My last scrap was with Puff Daddy, who would've thought it?/I bought that n***a album in seventh grade and played it so much/You would've thought my favorite rapper was Puff/ Back then I ain't know sh*t, now I know too much."

Puff Daddy had some words for Drake in 2014 when the two stars got into a heated discussion in Miami. As per the Miami New Times, Drake and Sean Combs came to blows outside of LIV nightclub in Miami Beach after attending DJ Khaled's event for Art Basel. 

Witnesses claim the two had it out for each other over music rights, and were seen arguing over the profits. While the heated discussion reportedly ended up physical, there's no confirmation as to who threw the first punch. Bystanders did, however, hear the music mogul telling the "6 God" rapper: "You will not disrespect me."

Diddy spoke out amidst claims that he punched the rapper, telling Power 105.1's "The Breakfast Club" (via MTV) that he never touched Drake. He did confirm that the pair discussed Drake's "0 to 100" track, saying, "'0 to 100' was initially a record that was my record, and then somehow that became ... just a misunderstanding, because we were working with the same producers," he shared. "Honestly it was a misunderstanding."

Diddy has quite the rap sheet — and we're not talking about songs. The music executive was arrested in 2015 after a violent argument with a UCLA football coach ended with him in custody. According to TMZ, the "Bad Boy For Life" artist was watching his son Justin's football practice when he overheard the strength and conditioning coach Sal Alosi "riding Justin, screaming intensely at him." That's when Puff Daddy reportedly stepped in, having words with the coach in his office that resulted in the Bad Boy executive allegedly grabbing the man.

Alosi allegedly refused to speak with Diddy, resulting in the music mogul threatening to call the police. Sources told the publication that "Diddy insists he grabbed a kettlebell and held it up in a defensive position ... but did not attack with an intent to injure the coach." Combs was allegedly charged with three counts of assault with a deadly weapon, one count of terroristic threats, and one count of battery, according to UCLA Police.

A representative for Diddy released a statement to the Associated Press saying, "The various accounts of the event and charges that are being reported are wholly inaccurate. What we can say now is that any actions taken by Mr. Combs were solely defensive in nature to protect himself and his son." Following the incident, the L.A. District Attorney's Office decided not to file assault charges against the producer.

Sean Combs is facing some shocking allegations against him from his ex-girlfriend Gina Huynh. In a 2019 interview with Tasha K that has resurfaced, the model says she dated Combs for five years and was repeatedly abused by him. Huynh claims she and Diddy started dating while he was on a break from his long-time girlfriend, artist Cassie, but the relationship was riddled with physical abuse. 

"He stomped on my stomach really hard — like, took the wind out of my breath," she alleged in the interview. "I couldn't breathe. He kept hitting me. I was pleading to him, 'Can you just stop? I can't breathe."' Huynh alleged she fought back after the rapper grabbed her hair and began punching her in the back of the head. Much of her injuries often went unnoticed as her hair covered up the tell-tale signs. "He would always compare me to Cassie and tell me that I'm the bad one, she's a good one," she said. 

The model said that Puff Daddy's inner circle knew about the abuse and allowed it to continue for years. She also claimed that Combs tried to pay her $50,000 dollars to get an abortion, which she refused. "I turned [the money] down because I just loved him. I wanted to ... I was, like, trying to prove that," she shared. As of the time of writing, Diddy has yet to respond to the allegations.

Sean Combs is not on good terms with his ex-girlfriend Cassie, especially after she claims the music mogul blew up a car in a fit of rage. The pair dated for over a decade before ultimately calling it quits in 2018. According to Entertainment Weekly, the "Me & U" singer filed a federal complaint against Puff Daddy, and alleged that he "blew up a man's car after he learned that he was romantically interested in Ventura" (Cassie's real name is Cassandra Ventura). Cassie went on to explain that her ex-boyfriend "frequently reminded Ms. Ventura of his ability to cause serious harm."

That said musician has been revealed to be Kid Cudi, whose representative confirmed Cassie's complaint in a statement. "This is all true," read a statement from the artist's spokesperson to The New York Times. Cassie claimed she and Kid Cudi were romantically involved while she was on a break from Combs in 2011. Upon learning of a correspondence between Kid Cudi and Cassie, Diddy allegedly attacked the artist. The following year, the "Day 'n' Nite" singer's car was found exploded in his driveway. Combs' attorney denied the allegations, describing them as "riddled with baseless and outrageous lies, aiming to tarnish Mr. Combs' reputation and seeking a payday."

Usher and Sean Combs have had a relationship for decades, one that started when the "Hey Daddy" singer was just 14 years old. But being taken under the wing of a powerful music mogul such as Combs was a loaded commitment, one that the R&B singer looks back on through a different lens now. 

In a 2016 interview on The Howard Stern Show, Usher admitted that his mentor L.A. Reid had sent him to live with Combs in New York City when he was kickstarting his career. The singer called it a "curious" experience, and while he denied Stern's claim that the house was "filled with chicks and orgying," it did leave a lasting impact on him. "I got a chance to see some things," he shared, adding, "I went there to see the lifestyle. And I saw it. But I don't know if I could indulge and understand what I was even looking at. It was pretty wild. It was crazy."

When Robin Quivers asked if Usher had any interactions with any women at Combs' place, he quickly interjected, saying, "I didn't say that. I didn't say that. What I did say is that there were very curious things taking place and I didn't necessarily understand it." Usher revealed that he was up into the early hours of the morning alongside some of the rap industry's biggest stars at the time, but when asked if he would place his own under Diddy's wing, he responded "Hell no."

Cassie launched a shocking lawsuit against her ex-boyfriend Sean Combs in November 2023, alleging she suffered years of physical abuse and sexual assault at the hands of the music mogul. The artist states she started seeing the fashion designer when she was 19 years old, claiming he raped her, physically assaulted her, and forced her to have sex with male prostitutes during their decade-long relationship together.

According to the singer, she was reluctant to come forward with the accusations for years for fear of retaliation from the music executive. Cassie alleges that the Sean John founder once dangled her friend over a balcony, and forced her to carry a gun with her at all times to ensure her protection. The singer also claims that Puff Daddy once paid a hotel employee $50,000 dollars to delete footage of him throwing glass vases at the star during an altercation. 

Combs and Cassie came to a settlement out of court just one day after the damning accusations were filed in court. "We have decided to resolve this matter amicably," the music mogul said in a statement. "I wish Cassie and her family all the best. Love."

Federal investigators have searched Diddy's properties in Miami and Los Angeles amidst a sex trafficking investigation. TMZ caught footage of Puff Daddy pacing around the Miami-Opa Locka Executive Airport just hours after the raids began in his homes, where he was reportedly stopped by Customs. While he wasn't detained, it was reported that he and members of his entourage were questioned by federal agents after flying in on his private jet.

The investigation comes months after Diddy denied sex trafficking claims lodged against him by his former girlfriend Cassie. As of the time of writing, Puff Daddy's whereabouts remain unknown. Federal investigators prevented the music mogul from departing the Miami airport en route to the Bahamas prior to takeoff, according to NBC News. He continues to maintain his innocence in light of the accusations claiming he was involved in a sex trafficking scheme.