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Diddy Paid His Friend Only $50,000 After 10 Years in Prison While Spending Half a Million Shopping For Cassie Ventura

When Moses ‘Shyne’ Barrow entered the spotlight in the late ‘90s, he was on top of the world—signed to Diddy’s Bad Boy Records, with big dreams. But as life often goes, things took a sharp turn. In December 1999, a nightclub altercation between Diddy and another man spiraled into gunfire. Caught in the crossfire, Barrow was sentenced to 10 years in prison for assault.

Diddy Paid His Friend Only ,000 After 10 Years in Prison While Spending Half a Million Shopping For Cassie Ventura
Diddy in a still from Black-ish | Credits: ABC

Now, as Barrow promotes his new documentary, The Honorable Shyne, he’s taking a closer look at the rocky relationship that once defined his career—specifically, the fallout with his former mentor, Sean ‘Diddy’ Combs.

Moses ‘Shyne’ Barrow Calls Out Diddy Over $50K After 10 Years in Prison

Moses ‘Shyne’ Barrow’s journey from rising star to incarcerated rapper-turned-politician has always been a tale of ups and downs. But it’s not just his music or his political career making headlines right now—it’s his relationship with Sean ‘Diddy’ Combs. After years of silence, Barrow is finally telling his side of the story, and it’s clear he’s still carrying a lot of hurt.

In a recent interview (via The Breakfast Club) promoting his documentary The Honorable Shyne, Barrow, 46, opened up about the bitter fallout from the 1999 nightclub shooting that landed him in prison. He and Diddy were close back then, but after a decade behind bars, the former found himself disappointed and betrayed.

There wasn’t an instant forgiveness. I got out in 2009. There wasn’t an attempt at reconciliation until 2012, when I went to Paris to meet him. That was the first attempt of forgiveness, but I was still in a place of, ‘He owe me. He owes me his life.’

He opened up about the fallout with Diddy after spending 10 years in prison.
Moses ‘Shyne’ Barrow | Credit: The Breakfast Club/YouTube

He felt he had more than earned his place in Diddy’s rise to superstardom. “He’s a billionaire. If it wasn’t for me, he wouldn’t have been a billionaire,” Barrow asserted, adding: 

If I would have cooperated with the district attorney, he’d have went to jail, and heaven knows what would have happened to his career. So that’s worth at least a couple million dollars out of the billion that you’re worth.

Yet, when Diddy finally made an attempt at reconciliation, it was more underwhelming than Barrow expected. After spending ten long years behind bars, he was given a mere $50,000:

He probably gave me, like, 50 racks, and I’m like, ‘You can’t be serious.’ That’s 10 years? Fifty racks?

This paltry sum, especially when compared to the lavish gifts Combs bought for his then-girlfriend, Cassie Ventura, left a sour taste in Barrow’s mouth.

Interestingly enough, one of the things that Cassie alleges in her lawsuit is that when Diddy would assault her, he would take her on shopping sprees. I saw that in Paris, he spent like a half a million dollars in one day shopping for her.

But Barrow didn’t stop there. 

Shyne Barrow Opens Up About Diddy, Prison, & His New Documentary

During the same chat on The Breakfast Club, Moses ‘Shyne’ Barrow also revealed that Diddy attempted a visit when he was locked up at Rikers Island. “He came to see me once, and I think I tried to spit in his face in Rikers Island,” Barrow recalled. 

Continuing, Barrow said:

I didn’t even want him to come see me. I didn’t even know he was coming to see me. They just brought me down in the lawyer’s office.

Shyne believes he played a key role in Diddy's rise.
Moses ‘Shyne’ Barrow | Credit: The Breakfast Club/YouTube

Recently, in an interview with CNN, Barrow didn’t mince words when it comes to the role Diddy played in his downfall. 

You know, there’s so many things that I said so long ago about Diddy. Nobody would listen, nobody would believe. And it makes the wounds that I’ve, by the grace of God, been able to heal, and the accomplishments that I’ve been able to achieve, even much more significant.

Barrow’s path to fame wasn’t easy. Now, in his new documentary, The Honorable Shyne, he takes viewers through his life, from his childhood in Belize to his rise in the rap game. 

The Honorable Shyne is now streaming on Hulu.

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