Diddy’s Crazy Rap Sheet: From Attacking a Record Exec to His Alleged Kettlebell Assault

The Bad Boy rapper-entrepreneur has a long, storied history of run-ins with the law, including his tussle with Drake, confrontations with fans, and that infamous nightclub shooting.

Mario Anzuoni / Reuters

Groundbreaking hip-hop mogul Sean “Diddy” Combs has added the title of “#1 Dad” to his lengthy resume, following a post-Father’s Day altercation on Monday at his son’s university, UCLA. According to TMZ, sources say the incident involved an argument between Diddy and one of his son’s football coaches. The rapper’s son Justin Combs is a defensive back who has seen little action on the field during his three years at UCLA. While officials have yet to comment on the identity of the victim or the motives behind the attack, we do know that Diddy was booked on three counts of assault with a deadly weapon, one count of making terrorist threats, and one count of battery. And the alleged deadly weapon? A kettlebell weight—a particularly unwieldy choice. No one was seriously injured in the attack, and Combs was released late Monday night.

So not cool, Dad.

In addition to a degree from the Stannis Baratheon School of violent parenting, Diddy has earned a reputation for serious crimes committed with hilarious objects. In fact, the artist formerly known as Puff Daddy or P. Diddy has more assault charges than pseudonyms. In 1999, Combs pleaded guilty to second-degree harassment after he allegedly beat down record executive Steve Stoute. Stoute accused the rapper of charging into his office with two buddies and hitting him with a chair and a champagne bottle. According to Stoute, Combs then threw “my desk over and they just walk out like nothing happened.” Let’s all take a moment to picture Diddy and two cohorts casually sauntering through a maze of corporate cubicles, dripping blood and Dom.

Combs adamantly denied breaking Stoute’s jaw and arm, although he did admit that “I let my emotions get the best of me and I just made a mistake.” Stoute and Combs both verified that the dispute stemmed from Nas’ video for “Hate Me Now,” which depicted both of the rappers nailed to the cross. Stoute, who managed Nas, knew that Combs was having crucifixion cold feet. So when the original video went public in spite of Combs’s removal request, the rapper made Stoute a sacrificial lamb for the sacrilegious blunder. Miraculously, Combs’s guilty plea to a lesser charge resulted in only one day of court-ordered anger management. These days, Stoute and Combs share bottles of champagne instead of beating each other up with them.

Unfortunately, Combs’s most serious crime of 1999 didn’t end similarly happily ever after. The infamous December Times Square shootout took place at a club that was actually called Club New York—and while some of the details are still under wraps, the extraordinary facts that we know have rightfully raised this incident to mythic status. The altercation began when Combs bumped into a fellow club-goer, spilling the man’s drink. Instead of respectfully requesting a selfie and then going on his merry way, the man became hip-hop history’s most idiotic John Doe by insulting and taunting Combs. The verbal sparring culminated in someone throwing cash at Combs in a derogatory manner, as one does. While Club New Yorkers dove for the dough, fellow rapper and Combs associate Jamal “Shyne” Barrow drew a semi-automatic and opened fire, wounding three bystanders. Before someone could diffuse the tension with a “that escalated quickly” joke, Combs had shot his own gun, just once, at the ceiling.

Combs and then-girlfriend Jennifer Lopez fled the scene in a Lincoln Navigator. After they were stopped by police and hauled to the station, Combs allegedly tried to bribe his driver to claim the gun as his own, offering a $40,000 diamond pinky ring as collateral. This story couldn’t be more ’90s if Combs had attempted to bribe his driver with an actual Ring Pop.

Combs was charged with gun possession and bribery, and faced 15 years in prison if convicted. Diddy’s kick-ass defense team included infamous O.J. Simpson lawyer Johnnie Cochran, who was doubtlessly thrilled to be representing a client who couldn’t aim. While Combs eventually walked free, rapper Shyne spent 10 years in prison. Over a decade after the shooting, Diddy was still dealing with repercussions, finally reaching settlements with all three victims in 2011. Natania Reuben, who was shot in the nose and reportedly has “seven bullet fragments still lodged in her face,” was awarded $1.8 million. As recently as 2010, Shyne was reportedly living in Jerusalem as a practicing orthodox Jew. He and Diddy have reconciled, while Diddy and J. Lo’s relationship couldn’t survive the shooting—a bitter victory for the awful adage “bro’s before hoes.”

Rounding out Diddy’s ’99 true crime trilogy was radio host Roger Mills’s accusation that he was roughed up by the rapper’s bodyguards. Mills alleged that he was attacked after an interview in which he asked if Combs had any part in Notorious B.I.G.’s murder. In 2004 Diddy denied the charges, testifying that he didn’t give any violent orders to his handlers. The courts ruled in favor of Combs, citing insufficient evidence.

The aughts brought little legal respite for the rapper turned businessman, who easily has more pending legal suits than actual suits. In 2004, promoter James Waldon filed a $5 million lawsuit against Diddy. Apparently, Waldon approached the rapper at Lower East Side hotspot The Box and invited him to see a hip-hop show he was promoting. According to court papers, “Combs gestured at (a bodyguard) to forcibly remove Mr. Waldon from close proximity to Combs,” unleashing three violent handlers who proceeded to hit and kick the promoter repeatedly.

In 2011, Diddy took brand loyalty to the next level when he shouted obscenities at a fan for drinking an alcoholic beverage that wasn’t the Diddy-endorsed Ciroc. The rapper was hosting a BET Awards after party with T.I. when he began meting out abuse on an unsuspecting crowd member. Despite the ice cubes that Diddy reportedly hurled from the stage, the club quickly got heated. While T.I. attempted to calm the crowd by chastising Combs for his Ciroc tyranny, unconfirmed gunfire later that night was attributed to Diddy’s aggressive antagonism. Clearly, post-recession Puff Daddy was a little too reliant on his novelty liquor-related revenue; too bad Ciroc sucks.

The year 2014 brought Diddy a relatively nonviolent beef with fellow rapper Drake. Sure, Drake went to the ER after Diddy punched him in the shoulder—but at least there wasn’t a gun (or a champagne bottle) involved. Apparently it was a classic case of stolen beat; Diddy alleged that Drake stole one of his tracks and played it as his own.

One year later, disgruntled Diddy fan Steven Donaldson claimed he was also punched by the rapper. In a TMZ video, Donaldson berated Diddy for arriving late to his scheduled appearance at a Super Bowl party. Donaldson, who probably wasn’t even drinking Ciroc, allegedly goaded the Diddy until one of his goons punched him in the face—and then he hit the rapper with a battery report.

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While Diddy’s rap sheet is arguably more impressive than his rap skills, his most famous alleged crimes never made it to court. In 2008, Los Angeles Times reporter Chuck Philips penned a now-retracted article alleging that Combs and the Notorious B.I.G. both knew in advance that Tupac Shakur would be attacked at New York’s Quad Recording Studios on November 30, 1994. Citing a combination of FBI informants and unnamed sources, Philips contended that the setup was partly motivated by Shakur’s refusal to join Diddy’s Bad Boy label. The 1994 incident infamously led to the Biggie/Tupac falling out that invigorated the East Coast/West Coast rivalry and eventually left both rappers dead. Diddy released a statement denying the story’s accusations, insisting, “It is a complete lie to suggest that there was any involvement by Biggie or myself.”

In 2011, former LAPD homicide detective Greg Kading published Murder Rap, which claims that Diddy ordered a deadly $1 million hit on Tupac. Kading, who participated in Tupac’s murder investigation but was eventually pulled from the case, insists that he has a taped confession from Diddy’s hitman. Combs called the book “pure fiction.” While Combs has somehow managed to dodge more charges than his football-playing son, we’re eagerly awaiting more reveals about the rapper’s criminal past—along with Justin Combs’s inevitable tell-all memoir.