It was the 10th round of the boxing match. When Buster Douglas landed an uppercut on Mike Tyson – arguably the most powerful boxer the world had seen. Douglas followed it up with a combination of four punches. And for the first time in his career, Mike Tyson was knocked out!

Tyson had never lost before this match. In fact, he had won 33 of his 37 matches with knockouts! Before the match, Tyson was given 42 to 1 odds that he would win. The bout came to be known as the biggest upset in boxing history!

So what went wrong? How did the undefeated Mike Tyson lose against a much weaker opponent?

The genesis story of the big bad Mike Tyson

Tyson had been arrested 38 times by the time he was just 13 years old. He lived in a crime ridden neighbourhood in extreme poverty. 

Fortunately for Tyson, a juvenile detention counsellor saw something in his fighting and introduced him to boxing manager Cus D’Amato. It was D’Amato who straightened Tyson out.

D’Amato gave Tyson discipline. Taught him boxing. And his partner Camille Ewald became a mother figure for Tyson. Tyson’s real mother passed away when he was 16 years old, when D’Amato and Ewald adopted Tyson! It was a life straight out of a movie.

D’Amato hired Kevin Rooney to be Tyson’s trainer. And built a whole team to help Tyson become the best boxer out there. Under D’Amato and Rooney, Tyson won the gold at Junior Olympics. And won the first 35 matches of his professional career. Tyson won 26 of his first 28 matches by KO or TKO!

Unfortunately, D’Amato passed away when Tyson was just 19 years old. Before Tyson became the youngest world heavyweight champion at the age of 20!

It felt like no one could stop Tyson. Except Tyson himself.

The derailing of Tyson

After the death of D’Amato, Tyson started giving in to his childhood instincts. His life sped up. He kept on winning. Kept on earning. Kept on spending.

The legendary Don King who had promoted everyone from Ali to Frazier took an interest in Tyson and got him better deals and more money. King was a problem fixer and made himself indispensable to Tyson by keeping minor legal issues at bay.

Tyson went on a crazy spree. Bought 7 mansions. And 200 cars. And partied hard every night.

And on advice of Don King, Tyson fired Kevin Rooney and everyone else in the team D’Amato had built for him.

Tyson forgot the basics

A boxer needs to train. And rest. Tyson forgot to focus on both. Rest and sleep were replaced by hard partying. But even his training went downhill.

Tyson was surrounded by yes men who didn’t challenge him. He stopped keeping his hands near his face for defence. His head movement declined. He had a nasty punch, and he started relying only on offence. He traded in all the defensive skills he had learned under D’Amato and Rooney for the whirlwind rapid assault.

And while Tyson was partying, Douglas was training and resting, training and resting.

Every boxing analyst credits Tyson’s loss to Buster Douglas to the absence of Kevin Rooney in his corner. Or to the death of Cus D’Amato – someone who could have kept Tyson disciplined.

The merits of good guidance

“Trees that grow up in their mothers’ shade grow slowly, because their moms block most of the sun. Slow growth leads to dense wood, which leads to a strong tree. Trees that instead grow in the open sun, without their mom’s shade, grow very fast, gorging on all the light they can absorb. But fast growth leads to soft wood, which is susceptible to rot and fungus.” – Morgan Housel

By giving up the shade of D’Amato and Rooney, and opting for the speed of Don King, Mike Tyson ruined his potential. His success derailed him. Surrounding himself with weak men made him weak. And his failures made him more vicious. His wife left him for abuse, and he was soon convicted of rape and imprisoned. 

Could Tyson have avoided it all?

How to find the right mentor?

If only Tyson would have avoided the fast life his success bought. If only he had remained disciplined. If only, he had retained the people who had raised him.

How could Tyson have known Don King was not the best manager for him?

Don King was a great schmoozer. He had cultivated a relationship with Tyson’s wife to get in Tyson’s good books. He paid a lot of attention to Tyson. But he was known to not have his clients best interests at heart.

After all, even Muhammad Ali had sued Don King. 

King’s words and actions were not consistent. And that is the biggest red flag.

You want a mentor who is not transactional. Who does not look for their own gains over yours. Who prioritises your long term growth over short term gains. 

If Tyson had reflected on the roots of his initial success, he would have been in a better place. If he would have steered clear of smooth talkers and the allure of glitz, he would have won more bouts. Today, he would be known as the greatest boxer of our times, and not just one of the greatest.

Action Summary:

• Don’t let the appeal of fast growth derail you. Put in the effort. Focus on the long term.

• Surround yourself with people who challenge you and make you better. Judge people on their history. And on their follow through. Not on their sweet words, but on their right actions.