Mike Tyson might be the best boxer in the world. But when managing his finances, he has loose hands in that department, and when he used to go on a wild spending spree, it usually ended in trouble. Who can forget that wild 15-year spending spree by Tyson that eventually ended in his filing for bankruptcy in 2003? The New York-born spent his entire $430 million fortune on cars, mansions, phone plans, rehabs, and whatnot.

He used to spend as fast as the money came, and no one could stop him. After learning the bad side of having money, Tyson rejected several deals that were worth millions. On the Jimmy Kimmel Show, Tyson revealed why he rejected an idea by Kimmel himself that would have earned the latter a whopping $20 million.

The deal in which Mike Tyson rejected $20 million

Kimmel wanted to know about the money that Tyson was making for his fight against Jake Paul. The talk show host was aware that both parties involved were making tons of money, but what he couldn’t wrap his head around the fact was that, 20 years ago, the former boxer rejected an idea by Kimmel that would have earned him at least $20 million. “I wanted to do a PPV roast and you would have made 20 million dollars. But you said, ‘No, I don’t want to do that because when I have too much money, bad things happen,'” stated Kimmel, wondering about the reason.

Tyson cheekily replied, “Well, I was a different person back then,” as the crowd erupted in laughter. The Nevada boxers accepted the fact that he did not know how to manage his money back in his younger days. He used to spend millions of dollars in a few days and was not even aware of the purchases most of the time.

Tyson remembered the time when he spent 5 million dollars in a week but did not buy anything. “Year, 5 million back in the day could go in 3-4 days. I am a heavy spender. Not now, when I was young, 5 million might go in a couple of days,” stated the boxer, mentioning the fact that he had changed now.

With age, he has attained wisdom and has finally learned to spend money wisely. He has helped so many people over the years so that they don’t make the same mistakes that the boxers made in the past. But given the number of times he has been in trouble because of money, Tyson must regret spending a little, right? Well, the boxer answered the question himself in the show.

Does Tyson have any semblance of regret over missing out on that deal?

After hearing about such audacious spending, Kimmel was curious to know whether there was a feeling of regret. Tyson didn’t waste a second as he replied, “Never, I had such a great time,” followed by a round of applause from the crowd.

At his peak, Tyson was such a free spender that no one was able to keep track. According to various reports over the years, in 2003, Tyson was almost $23 million in debt and owed $13.4 million to the IRS. This was just 2 years before his retirement, as at the time Tyson had several luxury mansions to his name, including the 52-room Connecticut mega-mansion. The 50-6 boxer had to sell that property to 50 Cent after declaring bankruptcy for $4.4 million.

He still boasts a brilliant car collection, and, as revealed by the man himself, he gifts those luxurious cars to anyone who needs them. The boxer also used to pet three ferocious illegal tigers in his early days, and who does not know about his large pigeon collection? There are almost 3,000 pigeons in his collection, and every bird used to cost around $3,000. All these expenses are just the tip of the iceberg when it comes to ‘Iron’. So, it might have been a correct decision to reject that $20 million once he was trying to improve his lifestyle.

What do you think about the boxing roast idea of Kimmel? Would it have been good? And was Mike Tyson right to reject the offer? Let us know your thoughts down below.