Diddy and Shyne Barrow’s History: 1999 Shooting and Beyond

In September 2024, Sean “Diddy” Combs was taken into federal custody on sex trafficking and racketeering charges and denied bail.

With a spotlight on the rapper's alleged years of criminal activity - Diddy pleaded not guilty to the charges - Moses "Shyne" Barrow reminded the world of another dark chapter of Diddy's history.

"This is someone who destroyed my life," Shyne said of Diddy during a September 2024 press conference in Belize.

Shyne spent more than eight years in prison after he, his then-mentor Diddy and Diddy's then-girlfriend, Jennifer Lopez, were involved in a shooting at a New York City nightclub in 1999. After an argument broke out, shots were fired and three bystanders were injured.

Shyne was accused of shooting the injured parties, though he has always maintained that he fired into the air. One injured witness, Natania Reuben, testified in 2001 that she saw Diddy fire a gun. Shyne was ultimately convicted on charges of first-degree assault, reckless endangerment and criminal possession of an illegal weapon, while Diddy was found not guilty of four weapons-related charges and bribing his driver to claim ownership of his gun.

"Everyone knew all along that I was the fall guy," Shyne said of the shooting during an April 2024 press conference. "Everyone knew, that was the story. … I maintain my innocence."

A Timeline of Diddy's Legal Troubles, Accusations and Arrests

Keep scrolling for a look at Shyne and Diddy's history over the years:

1998

Shyne got the attention of record producer DJ Clark Kent while freestyling in Brooklyn. Kent then introduced the young rapper to Diddy, who quickly signed Shyne to his label Bad Boy Records.

1999

Shyne's life was forever changed by the December 27 shooting at Manhattan's Club New York. Diddy, Shyne and Lopez were all initially arrested, detained and charged for their involvement, but the charges against Lopez were quickly dropped.

2001

After a weeks-long trial, Diddy was found not guilty of all charges related to the shooting while Shyne was sentenced to 10 years in prison without the eligibility for parole until 2009.

2009

Shyne was released from prison in October 2009.

“It’s a blessing that he’s coming home,” Diddy said in an interview on Hot 97 shortly before Shyne's release, per CBS News. “I spoke to him like a couple of weeks ago and he sounded like he was in good spirits.”

Four weeks after Shyne's release, he was deported to his home country of Belize despite spending much of his life in the United States. He moved to Brooklyn to live with his mother when he was 7 years old but continued to spend summers in Belize with his father.

After his deportation, Shyne went on to have a career in politics and is currently the Leader of the Opposition in the Belize House of Representatives and the leader of the Belize United Democratic Party.

Eyebrow-Raising Quotes About Diddy's Alleged Behavior Over the Years

March 2012

Shyne and Diddy were photographed sitting side by side at a Fashion Week show in Paris.

"You can’t overstate the cultural significance of what Shyne and Diddy reconciling means," Shyne told XXLMag in a statement at the time. "You know I’m about it when it comes to them hammers, thus unfortunately this could have ended like Tupac and B.I.G. But what if Tupac and B.I.G ended like this and reconciled? Let’s celebrate this moment as a historical event and a victory for hip-hop and Afro and Latin American men trained to exterminate each other. It’s a new day! L’chaim!!!"

April 2012

Shyne spoke out about his time in prison during an appearance on 7 News Belize.

“The entire process was devastating. Ten hours of incarceration is ten hours too much. So, for a human being to be animalized for ten years, there is no quick fix to that," he said. "When I came out I didn’t even realize how wounded and devastated I was because I numbed myself to the pain and destruction that I suffered.”

He also recalled how difficult it was when his mother came to visit him.

"My mother couldn’t look at me; she would start to shake, and she would go off the floor and go to the bathroom. I couldn’t process that because if I cried in front of her then that would make her life go to shambles," he explained. "If I cried in front of the prison guard, they would think that I was weak. So I go back to the yard and lift some weights, smoke a cigar and act like nothing happened. When you come out from that, how do you recover?"

August 2012

Despite seemingly mending fences, Shyne took aim at Diddy on his diss track "You're Welcome," addressing the events that led up to his incarceration.

"I need to know, how my co-d called witness to sacrifice me just so he can get away free? / This does not comply with the streets," Shyne rapped. "But he ain't from there, this is not a smear / This is what they fear, the whole truth, I swear."

November 2022

Shyne announced that Diddy had agreed to pay for one Belizean student's full scholarship to Howard University in the United States.

"Education has always been extremely important to my dear brother Diddy and I thus in that vein asked Diddy to make Belize a part of his philanthropic support for his alma mater, Howard University, so that at least one Belizean Student can get the benefit of attending one of the United States’ most prestigious HBC Universities," Shyne said in a statement at the time, per Loop Caribbean News. "I thank Diddy for always supporting my efforts to help Belize in every way possible."

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March 2024

The 1999 shooting made headlines once again, the same month that Diddy's Los Angeles and Miami homes were raided in connection to a sex trafficking investigation. Natania Reuben appeared on NewsNation to claim that Diddy, not Shyne, had shot her in the face that fateful night.

"I'm willing to have a doctor remove a part of the 9 mm bullet in my face so that they can use it as evidence if need be for this trial," she said. "Who better to tell you what happened than the person who got shot smack dab in between my eyes?"

April 2024

Shyne reacted to Reuben's new comments about the shooting in a press conference.

"It opens wounds when you hear the victim saying it was Diddy that shot her," he said. "I've done my best to put it behind me and to move forward, but it certainly reopens the wounds that I've been saying this all along. Everyone knew all along that I was the fall guy but my political enemies and detractors tried to make me into this criminal, but everyone knew that I was a young kid that took the fall. Everyone knew, that was the story. … I maintain my innocence. … I am relieved that people are saying what the truth is: that I did not shoot those people."

September 2024

Shortly after Diddy was taken into federal custody on charges of sex trafficking and racketeering, Shyne was asked about his history with the music mogul during a press conference in his native Belize. Shyne stated that he had "no business relationship" with Diddy despite their earlier collaboration on scholarships for Belizean students.

"Let us not lose sight of what the cold, hard facts are. This was not someone who I vacationed with and [with whom] I enjoyed this great, intimate relationship of brotherhood. This is someone who destroyed my life and who I forgave … for the better interest of Belize," Shyne said. "Because he was in a position at that time to give scholarships and maybe invest. I would not deny attempting to bring the investment to Belize."

Shyne also said that Diddy "testified against" him during his 2001 trial.

"I was defending him and he turned around and called witnesses to testify against me and he pretty much sent me to prison," he said. "That is the context by which you must also describe that relationship."

Despite their painful history, Shyne said he "absolutely [does] not" take "any joy or satisfaction" in Diddy's arrest as incarceration is something he wouldn't wish on his "worst enemy."

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This story was originally published September 20, 2024, 10:18 AM.