"He Pretty Much Sent Me to Prison" — Shyne Says His and Diddy's Relationship Has Never Fully Recovered

As many of Sean "Diddy" Combs's celebrity friends have been criticized for their silence on his September 2024 arrest, his former artist, Shyne , has plenty to say.

Shyne, real name Moses Michael Levi Barrow (and born as Jamal Michael), clarified in a recent interview that he has no sympathy for Diddy, given their history.

What happened between Shyne and Diddy?

Shyne and Diddy's professional relationship began when the Bad Boys CEO when Shyne signed onto the music label in 1998. He had hits like his first single, "Bad Boyz," and was about to release his first album when his and Diddy's troubles began.

On Dec. 27, 1999, the former collaborators celebrated the album's debut at a New York nightclub. Diddy's then-girlfriend Jennifer Lopez also attended the event.

During the outing, Diddy and another club attendee argued when Diddy knocked a drink out of the other man's hand. Gunshots were soon fired, leaving three bystanders injured. Diddy, J.Lo, and Shyne were arrested, but Shyne was the only one who served prison time. In June 2001, he was convicted of assault and was sentenced to 10 years in prison. Diddy and his bodyguard were acquitted of the charges.

Shyne continued working on his music career in prison, with his debut album still being a success. He was released from prison in 2009 and moved to Jerusalem and later his home country of Belize. He and Diddy reconnected and the artist forgave his former mentor. However, Shyne told a Channel 5 reported in Belize in September 2024 that he never forgot Diddy's betrayal.

"I was defending him, and he turned around and called witnesses to testify against me,” Shyne said.

“He pretty much sent me to prison. That is the context by which you must always describe that relationship. Yes, I forgave. I moved on. But let us not pretend as if I was in Miami for Thanksgiving and Christmas.”