This week in 1990, Mike Tyson took the first loss of his professional career to James “Buster” Douglas via knockout. It is still considered the biggest upset in boxing history and one of the biggest upsets in sports history.

Tyson was considered unbeatable at that time. Going into the fight against Buster Douglas, Tyson was 37-0 with 33 wins by knockout. Several of those knockouts were in the early rounds of those bouts.

The Brooklyn, New York native was running through the heavyweight division and everyone expected that to continue against Douglas. Douglas was 28-4-1 going into the bout. Buster was a 42-1 underdog from a betting perspective.

The Path to an Upset

There have been rumors that Tyson didn’t take the fight seriously, didn’t train properly, and this was part of the reason he suffered his first defeat. The main reason was that Douglas fought the best fight of his life.

Tyson was able to beat his previous opponents mentally before they entered the ring. He had this aura about him that scared most human beings. Buster Douglas is not most human beings. He went into that fight with no fear.

Douglas’ mother died during the training camp for this fight, which gave Buster even more motivation. If he was going to go out, he was going to go out with a bang. Douglas started the fight off by being the aggressor and making Tyson fight off of his back foot.

Tyson was not used to this and struggled to get into a rhythm early in the bout. Douglas won six of the first seven rounds on the scorecards. Then in the eighth round, Tyson unloaded on Douglas with a signature uppercut.

Tyson and his camp complained that it was a long count but Douglas beat the referee’s 10 count, which is all that matters. This is where everyone expected Tyson to take over but that did not happen. Douglas was able to take control of the fight in the next round, winning the ninth round on all the judges’ scorecards.

Then in the 10th round, Douglas landed a lethal combination that ended with Tyson down on the canvas. Tyson was able to get up but was still on dream street and the referee called it off.

The Impact of the Upset

Evander Holyfield was awaiting the winner of Tyson, Douglas, which everyone assumed would be Tyson. Holyfield has gone on record stating that he was set to make at least 12 million dollars guaranteed against Tyson if they fought in 1990.

Instead Holyfield took on Douglas and got paid 8 million while Douglas made 24 million dollars. Holyfield outclassed Douglas, knocking him out in the third round and Douglas’ win over Tyson was seen as a fluke.

If Mike Tyson would have defeated Buster Douglas, he would have fought Evander Holyfield in 1990. Holyfield at that time was 24-0 and in his physical prime at 27 years old. This is prior to the wars with Riddick Bowe, the heart condition, and the wear and tear of being in his mid-30s like he was when he finally fought Tyson in 1996.

The best version of Holyfield was in the late 80s and early 90s. If Tyson fights Holyfield in 1990, I believe that Tyson gets beat and there is no excuse for Tyson. Now, of course there is no way to prove this but when watching Holyfield’s fights, the difference in quickness and power is apparent from his late-20s to mid-30s.

Since they didn’t get to fight until 1996, Tyson fans, make excuses like, “Tyson was passed his prime.” Even though Holyfield is four years older than Tyson and was in more brutal fights than Tyson was.

The boxing fans who love Tyson are able to point to a “reason” for each loss of his career. He was dealing with splitting ways with his long time manager, Bill Cayton and trainer, Kevin Rooney prior to his loss against Buster Douglas, they say.

Some fans will say, “Tyson was not the same after spending time and in jail and was passed his prime against Holyfield in the first fight.” Tyson was coming off of four straight wins and was a huge betting favorite over Holyfield going into the bout.

The biggest Tyson apologist will say, “In the second fight against Holyfield, Tyson was frustrated by Holyfield’s headbutts and that’s what led to him biting a piece of Holyfield’s ear off.”

Making excuses for Tyson biting off of a piece of Holyfield’s ear and getting disqualified is beyond wild!

“Against Lennox Lewis, Tyson was washed up,” some fans will say. Even with Tyson and Lewis being the same age.

All of these excuses start with the loss to Buster Douglas. If that loss doesn’t happen, history is completely different. Tyson’s legacy would be one of someone who loss to the greats of his era instead of this mythical legacy that has been built around four years of dominance, early in his career.

Douglas’ win being viewed as a fluke allows fans of Tyson to dismiss it and say he would of never loss during his “prime” if he stayed focus.

When the truth is, Tyson was a great talent but was not the best of his era. The aura of Tyson is greater than the reality of Tyson and this anniversary is a big reminder of that.