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The Question: What’s The Most Memorable Upset?

By James Guttman, James Bullock, and Dan Crocker Nov 30, 2016 - 10:05 AM print

It's time for another edition of "The Question" - We Want Insanity's weekly answer to something we all have our own opinion on. See what we have to say and then share your own. That's what questions like this are for...

What’s The Most Memorable Upset?

James Guttman:

Before he was a meme that replaced the letter “s” with “th”, Mike Tyson was a monster. His fights were the stuff of legends. Every match he engaged in finished in record time. He barrelled through opponents and offered to fight the press at every turn. When questioned about his temperament, Iron Mike answered with such iconic lines as “I’ll f**k you until you love me, f*****t!”

His dominance was so impressive that it even inspired songs in the key of cornball care of Will Smith:

So needless to say, people were growing sick of waiting months for fights that lasted all of 90 seconds. To squash this problem, his camp decided to offer fans a new fight every month against lower level opponents. To this day, I’ll never forget the TV Plus insert from Newsday proudly declaring it “The Bum of the Month Club”.

One of the very first “bums” was ready to surprise the world as James “Buster” Douglas knocked Tyson out in round 10 – much farther than any other fighter had taken him. Not only had Mike never been knocked out. He’d never even been knocked down. It was insanity. At the time, Douglas was a 42-1 underdog and Tyson was superman. The atmosphere was unbelievable as no one saw this coming. No one.

To this day, I will never forget the feeling when Douglas landed that final shot. I jumped up and hopped around the house. I wasn’t sure what to do with myself. It was a feeling of pure adrenaline and shock that has yet to be recreated in my lifetime.

A few years ago, when I hit my ten year anniversary of Raw Insanity, Buster Douglas posted a congratulations message to me on Facebook and it was truly a highlight of my writing career. When someone tells a younger person that they’ll never understand witnessing the dominance of someone like Mike Tyson, they should also add that they’ll never experience an upset like Buster Douglas. It was a truly a moment in time that anyone who saw it happen will never forget.

James Bullock:

When presented this week’s question following what has to be one of the most surprising moments in recent wrestling history my mind moved past Brock Lesnar’s pale body resembling a pile of mashed potatoes sponsored by Jimmy John’s to some of the moments in boxing and MMA history that left me with my mouth gapped like some slack-jawed yokel. Fights like Matt Serra-Georges St. Pierre I, Anderson Silva-Chris Weidman I, Hasim Rahman-Lennox Lewis, and even old footage featuring a young Cassius Clay besting Sonny Liston when the future Muhammad Ali demanded the news press to, “Eat your words!” While one fight stood out more than any other initially, I can’t give it to Holly Holm vs. Ronda Rousey for shaking up the world because the original “Buster” his due. That’s right – there’s no greater upset in modern history than James Douglas vs. Mike Tyson.

In February 1990, James “Buster” Douglas entered the Tokyo Dome as a 42-1 underdog to battle one of the most brutal knockout artists in pugilistic history in hopes of winning the Heavyweight Championship. Undefeated and having slaughtered his last opponent in less than two minutes, Tyson came into the fight with the media claiming he’d do the same to Douglas in nothing short of a tune-up fight to get his mind off his personal and managerial problems. Douglas also wasn’t entering the fight mentally 100% or even physically well as his mother passed, his son’s mother was suffering from kidney ailments, and he himself contracted the flu only a day prior to the fight. When the bout began, Douglas didn’t let anything stop him from taking the fight to a man who struck fear in the hearts of almost everyone he fought prior by keeping the champ on the outside and avoiding dogfights that would’ve been detrimental. Then the eighth round came and Douglas walked into an uppercut that dropped him for nine controversial seconds (controversial because, according to everyone in Tyson’s camp claimed was a “long nine count”).

By the ninth round it seemed the end was nigh for Douglas as the champ turned up the output and was actually landing. Douglas, hurt but not out, took to engaging Tyson in slugging it out until the tenth round. “Buster” actually did a great amount of damage joining in a dogfight one round prior, landing a devastating uppercut topped by four more punches aimed at Mike’s head that left him on the canvas, fumbling with his mouthpiece and unable to fully get up in time to unexpectedly give way to a new World Heavyweight champion. Even as a kid without really any knowledge of boxing, I understood just how monumental the win for Douglas was as he gave honor to his mother for believing in him when no one else did.

Dan Crocker:

For people of a certain age, there's really only one answer to this question. Some of you young folks might remember the Red Sox coming back from 3-1 to beat the Yankees. You might remember the Giants beating the undefeated Patriots. But nothing, nothing, could have shocked you all as much as Buster Douglas knocking out Mike Tyson shocked Generation X.

Tyson was considered unbeatable. He didn't just beat opponents, some of them great boxers themselves, but he annihilated them—knocking them out one by one in a round or two. And who the hell was Buster Douglas? No one knew. It was just going to be a tune up match. HBO showed it at like four in the morning because they didn't think anyone would be that interested. So what if Tyson wasn't taking it seriously? So what if he was a little out of shape and having some personal problems? He was a killing machine.

Or so we thought:

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