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Years After Losing His $430,000,000 Fortune, Mike Tyson Makes a Confession About His Gambling Nights With “Gangster” Rapper

Published 09/28/2023, 12:45 PM EDT

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In a world where sports icons and music legends seem larger than life, Mike Tyson’s recent confession left many stunned. On an episode of Hotboxin with Mike Tyson, the boxing champ revealed unexpected tales of gambling, dice, and… MC Hammer? Yes, the “U Can’t Touch This” rapper and Tyson once crossed paths, and not in the way you’d imagine. Forget the boxing ring or the music stage; the thrill of dice games, lost money, and unforeseen camaraderie defined this experience.

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A surprising chapter from Tyson’s tumultuous past is unfolding, providing a glimpse into nights of adrenaline, chance, and costly bets. As Tyson once reigned supreme with a $430 million fortune, these revelations give us a curious insight into where some of that money might have danced away.

Mike Tyson reveals high-stake dice games with ‘Gangster’ rapper


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MC Hammer, the iconic rapper who became a household name in the 90s with his hit “U Can’t Touch This,” wasn’t just known for his flashy pants and catchy tunes. Beyond the music scene, he shared an unexpected connection with none other than Mike Tyson, the boxing titan who once held the world’s attention with his formidable punches and fierce presence in the ring.

Transitioning from their individual realms of sports and music, the duo found common ground in the world of dice games. This surprising revelation came to light when Mike Tyson candidly reminisced about his gambling escapades with Hammer on his podcast.


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Mike Tyson began, “We did play dice all night talking sh*t.” Curiously, Symba inquired, “What’s the most you ever lost playing him?

Tyson’s response was both casual and revealing: “Me? I’m playing Hammer, that’s nothing I’m 30. But I wasn’t thinking about gambling, these guys just ripped me up. I was just High.” Undeterred, Symba delved deeper, “And they throw you in a dice game?” Mike confirmed, “Yeah, they did.”

Expanding on the narrative, Symba reflected, “They just be like let’s shoot Dice, that’s crazy.” DJ Whoo Kid, bringing a different perspective to the table, asked, “Did you enjoy hanging in the Bay Area?”

Tyson’s reply painted a broader picture of their interaction: “I never hung out in the Bay Area, only when he was on tour or something in different cities. One day he got me for 12,000 and another time again for 19k. He got a bunch of us playing but it’s just so awesome like the excitement’s worth the money.”

How Mike lost his fortune

Mike Tyson’s rise to fame and fortune was nothing short of meteoric. At the pinnacle of his career, his wealth soared to an astonishing $430 million. However, the tale of his financial unraveling is as captivating as his boxing prowess. His fall from financial grace was the result of an amalgam of unbridled spending, legal troubles, and poor financial management.

A significant chunk of Tyson’s fortune was squandered on a luxurious lifestyle filled with ostentatious purchases. He famously spent $2 million on a bathtub, $140,000 on two Bengal tigers, and a whopping $4.5 million on cars and motorcycles. His spending knew no bounds, with millions more frittered away on jewelry, parties, and a myriad of other extravagances.

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Moreover, Tyson’s legal entanglements further drained his wealth. His incarceration for rape in 1992 not only cost him lucrative fight opportunities but also led to hefty legal fees. The divorce settlements and subsequent child support payments further exacerbated his financial woes.


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Mismanagement was another critical factor in Tyson’s financial demise. Despite his substantial earnings, Tyson had a lack of financial acumen and relied heavily on an entourage that reportedly did little to curb his spending. His trust in unreliable financial advisors led to misguided investments, contributing to his economic downfall.

Tax woes were the final nail in the coffin. Tyson owed the IRS $13.4million, which played a significant role in driving him towards bankruptcy in 2003. By that time, the former boxing titan found himself $23 million in debt, a staggering figure considering the fortune he had once amassed.

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So, it begs the question: How much do we truly know about the lives of our icons beyond the limelight? And what other surprising tales remain untold?

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Written by:

Mrinal Mishra


One take at a time

Mrinal Mishra is a Boxing writer at EssentiallySports, who is dedicated to covering live events with a special emphasis on influencer boxing events. With a focus on storytelling, Mishra strives to bring to light the stories of fighters that often go untold. As a big fan of Mike Tyson, Mishra believes that boxing will remain relevant for eternity, and he is committed to covering the sport with the respect and admiration it deserves.
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Edited by:

Snigdhaa Jaiswal