Mike Tyson may be regarded as one of the greatest boxers of all time, but when it comes to managing his finances, he has often been reckless. His notorious spending sprees led to significant trouble, culminating in his bankruptcy filing in 2003 after squandering an astounding $430 million on lavish cars, extravagant mansions, extravagant phone plans, rehab sessions, and various other indulgences.

Tyson had a reputation for spending as quickly as he earned, leaving no one capable of stopping him. After experiencing the pitfalls of sudden wealth, he turned down several lucrative deals. One notable instance occurred on The Jimmy Kimmel Show, where Tyson shared a surprising moment from his past: he declined a lucrative idea from Kimmel that could have earned him a staggering $20 million.

Kimmel questioned Tyson about his earnings from a recent fight against Jake Paul, acknowledging the financial success both fighters enjoyed. However, he was astonished to recall that two decades earlier, Tyson had rejected a proposal that would have netted him at least $20 million. “I wanted to do a PPV roast, and you would have made $20 million. But you said, ‘No, I don’t want to do that because when I have too much money, bad things happen,’” Kimmel explained, seeking clarity on Tyson’s decision.

In response, Tyson humorously noted, “Well, I was a different person back then,” eliciting laughter from the audience. Reflecting on his past, Tyson admitted he lacked financial wisdom during his younger years, recalling times when he would spend millions in just days, often without awareness of his purchases.

He reminisced about a week where he spent $5 million but didn’t actually buy anything. “Back then, $5 million could disappear in just 3 or 4 days. I was a heavy spender,” Tyson confessed, indicating that he has changed his ways as he matured.

With age has come wisdom, and Tyson has learned to manage his money more prudently. Over the years, he has also supported many individuals, helping them avoid the financial mistakes he made in his own life. Despite the numerous financial troubles he encountered, Tyson surprisingly expressed no regrets about his past spending habits during the show.

When Kimmel probed whether Tyson felt any regret over the missed opportunity, Tyson responded instantly, “Never, I had such a great time,” which was met with applause from the audience.

At the height of his career, Tyson’s spending habits were so excessive that it was nearly impossible to keep track of his finances. Reports indicate that by 2003, he was approximately $23 million in debt, including $13.4 million owed to the IRS. This was just two years before his retirement, during which he owned multiple luxury mansions, including a sprawling 52-room estate in Connecticut. After declaring bankruptcy, he sold that mansion to rapper 50 Cent for $4.4 million.

Despite his past financial issues, Tyson still has an impressive car collection and revealed that he often gifts his luxurious vehicles to those in need. He is also known for having owned three exotic and illegal tigers during his early years, not to mention his extensive collection of nearly 3,000 pigeons, each valued around $3,000. These extravagant expenses are just a glimpse into the lavish lifestyle he once led. In hindsight, rejecting that $20 million deal might have been a wise decision as he sought to improve his financial habits.

What are your thoughts on Kimmel’s idea for a boxing roast? Would it have been a good opportunity for Tyson? Was he justified in turning it down? Share your opinions below!