“I never did it, that’s my biggest regret”: Mike Tyson Regrets Not Doing One Thing With Tupac Shakur Before His Death

"I never did it, that's my biggest regret": Mike Tyson Regrets Not Doing One Thing With Tupac Shakur Before His Death

Boxer Mike Tyson and Rapper Tupac Shakur’s close friendship was famously known which is why Tyson, like many others, was profoundly saddened by Shakur’s untimely death in 1996. But there was one pastime Tyson never engaged in with Shakur prior to his passing. Since then, Tyson has said that it is his biggest regret.

Mike Tyson
Mike Tyson

One Night in Vegas: Tyson & Tupac, a documentary that aired on ESPN, explores Tyson’s friendship with Shakur. In a phone interview, Tyson claims how Shakur always wanted Tyson to smoke pot with him but he never did, and now the boxer wished he did.

Tyson claimed he declined because he was a closet and didn’t want his drug use to be discovered. He now expresses remorse about the missed chance, saying, “That’s my biggest regret.”

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Mike Tyson describes his time with Tupac Shakur as “explosive”

Mike Tyson
Mike Tyson

Mike Tyson was greatly affected by his friend Tupac Shakur’s demise. Recalling his deceased friend, Tyson describes his precious moments with Shakur as “explosive”. Tyson said,

“He didn’t last long, but the time he did last, every minute, every tenth of a moment was explosive. He’s going to last until the time this Earth comes to an end, I’m glad to be a part of his life and to have known him.”

Speaking about his regret of not smoking marijuana with Shakur, Tyson added,

“He always wanted me to smoke weed (marijuana) with him, and I never did it, and I wish I did.That’s my biggest regret,”

Hearing all of this, its almost impossible to imagine that Mike Tyson had no idea who Tupac Shakur was when they first met

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Not knowing who he was, Mike Tyson first met Tupac Shakur at a club

Mike Tyson
Boxer, Mike Tyson

When he first met Tupac in the 1990s, Tyson was at the pinnacle of his fame and influence. According to Tyson, the rapper and he first met in a posh club. But Tupac was only getting started at this point, whereas Tyson was already well-known. While Tyson was at the club, a random man approached the boxer and requested entrance. When Tyson agreed, the guy and his group of pals entered the club. Tupac just so happened to be one of them.

But their friendship only grew until after Tyson ended up in prison. Explaining it, Tyson said in an interview with Power 106

“I went to prison, and he wrote me a letter, Then he came and saw me. Then he explained to me who he was, I said, ‘I remember you.’….And that’s how we became friends. He kept coming, we talked on the phone, and we really cultivated our relationship.”

The 25-year-old rapper was shot after a Tyson fight in Las Vegas on Sept. 7, 1996; he died six days later.

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Source : Cheat Sheet







Written by Aastha Soni

A cinephile with immense love for words and everything art. I have an inclination towards understanding human pschology but I prefer dogs over humans any day. I have an affinity for all kinds of music, except techno. Kind of an old soul, trying to tolerate today's typical "Gen Z mindset".