A lot of answers here are saying Holyfield beat Tyson by simply not being afraid of him. This is nonsense. While not being afraid of Tyson certainly helped Holyfield enact his game plan, it wasn’t the kryptonite that defeated Tyson. You don’t get to be at the elite level that Tyson was by being completely dependent on your intimidation factor.
A lot of answers here also claim that Holyfield defeated Tyson by outfighting him from the inside. Again, this is not quite correct, as I will explain in a bit.
The correct answer, is that Holyfield outfought Tyson from the clinch:
So what’s the difference between infighting and clinch fighting? In-fighting is staying close to your opponent, usually at a close enough distance where uppercuts to the face can easily be executed but sometimes so close that you’re already leaning on each other, then staying in that pocket while you try to cleanly box with your opponent. Keyword here is cleanly box. Because once you start trying to grapple with your opponent and wrapping them up, that’s now considered clinch-fighting, and trying to fight from inside a clinch is a completely different ballgame from simply boxing on the inside. This kind of fighting uses an entirely different skillset.
Holyfield didn’t defeat Tyson by cleanly boxing with him from a close distance… which is what in-fighting would have been. Rather, Holyfield would try to catch Tyson a few times as Tyson charged in but as soon as Tyson started throwing his own punches, Holyfield would clinch Tyson and break his rhythm. From there, Holyfield would wrestle Tyson, lean on him, smother him, throw a few punches here and there while he keeps Tyson wrapped up, even sneak in a few headbutts, then once they break he’d use the opportunity to hit Tyson with a few power shots then clinch again as soon as Tyson starts to gain momentum.
You’ll see in that clip above how Holyfield breaks off to deliver a few shots, then as soon as Tyson starts retaliating Holyfield bulls into him (usually leading with his head) then wraps him up. He did this repeatedly throughout both of their matches, enough that he would get warned every now and then by the referee for excessive clinching but never enough to truly get penalized.
A lot of people are using Tyson’s loss to Holyfield as proof that Tyson wasn’t a good in-fighter. This is ridiculous. Tyson was a terrific in-fighter, and he destroyed majority of his opponents from the inside. Heck, his favorite knockout combination was done at extremely short distances.
And that’s his weakness. His kryptonite: Fighting from the clinch:
Tyson only ever had 2 gears: stop and go. He was either at 0 mph or at 100 mph. He didn’t have the patience or mental fortitude for the slow, grinding pace of wearing down opponents in the clinch.
So everytime someone clinched him he usually only had 2 responses. Either he became surprisingly docile, not really doing much until the referee broke them apart, or he became extremely aggressive. Trying to throw elbows, forearms, attempting arm breaks, and then there was that infamous ear bite. Which meant either his opponent had a good opportunity to outwork him in the clinch (assuming his opponent was decently skilled) or he engaged in attacks that gets him warned by the referee or outright disqualified.