Fight Freaks Unite

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35 years after Douglas' historic upset of Tyson, a story and show and tell

35 years after Douglas' historic upset of Tyson, a story and show and tell

It's the anniversary of boxing's biggest upset and a great fight

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Dan Rafael
Feb 11, 2025
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Fight Freaks Unite
Fight Freaks Unite
35 years after Douglas' historic upset of Tyson, a story and show and tell
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A note to Fight Freaks Unite readers: I created Fight Freaks Unite in January 2021 and eight months later it also became available for paid subscriptions for additional content — and as a way to help keep this newsletter going and for readers to support independent journalism. If you haven’t upgraded to a paid subscription please consider it. If you have already, I truly appreciate it! Also, consider a gift subscription for the Fight Freak in your life.

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Those who saw it won’t ever forget it. And even if you weren’t watching live, it was the kind of event that you remember where you were and exactly what you were doing when you heard that 42-to-1 underdog James “Buster” Douglas, who wasn’t expected to last even a few rounds, had done the impossible: He knocked out the supposedly indestructible Mike Tyson in the 10th round to win the undisputed heavyweight championship.

Decades later it remains the biggest upset in boxing history, a simply unfathomable result, and one of the biggest upsets in sports history. It took place 35 years ago Tuesday — Feb. 11, 1990 — on an early afternoon in Tokyo in order to accommodate the live prime time telecast on HBO in the United States (where it was still Feb. 10).

Truth be told, I did not watch it live and was not happy about that. I was a sophomore in college and got quite ill a couple of days before the fight, which I had planned to watch at a friend’s apartment off campus as there was no HBO in the dorms. We were lucky there was even basic cable in the dorm lounge.

Here’s what happened and then a look and explanation of several fight-related items in my collection:


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