How the heck did Holyfield Tyson, TWICE?

Because styles make fights. Because Holyfield wasn't intimidated by Tyson (unlike the grand majority of Tyson's foes, who were beaten mentally before the bell even rang.) Because Tyson is an overrated, glass-jawed ***** and world-class bum beater. Those reasons.

In addition to all of the excellent points, Holyfield had a world class chin. He was ultimately in there with Bowe (3x), Lewis (2x), Tyson (2x), and Foreman -all of them big punchers -and his chin never let him down (save vs Bowe). That man could take a serious punch. And during that first Tyson fight he swallowed some massive shots and either held his ground or kept pressing forward, walking Mike down.

Evander had no fear of Tyson. In the first fight, he used his height advantage to smother him. In the second fight, Tyson was having more success, but got frustrated and lost his mind. Evander knew how to have a gameplan and carry it out for 12 rounds. Tyson didn't have a plan b

Here's the thing about Tyson, he fought a lot of tomato cans to make his name. Then he fought some has beens and never weres. It wasn't all his fault as it was a weak division when he came up, but some of it was his promotion, his first 20+ fights where he was getting high light reel KO after KO were against remarkably bad fighters. Less than club fighters, more like guys that were new tonyhenpowerto of boxing and had been in the bar drinking beers all night the night before. GGG would blush at the weakness of Tyson's first couole dozen opponents. And then when he did start fighting some champs, they were the Burbick's and Thomas's, this was not an era with good fighters in that division. The super fight vs Spinks was a sham because something was mentally wrong with Spinks. So Tyson fought a bunch of bums, Holyfield wasn't a bum and he destroyed the myth. He was simply better than Tyson. Bowe would have crushed Tyson too. And we all saw what Lewis did to Tyson even though Mike was past it by then. And I was a huge Tyson fan, I just an be honest looking back that he was more hype than substance as a fighter.

Because he was better than Tyson. Point blank period.

Tyson was never the same fighter after he got out of jail and was feasting on bums for two years leading up to the Holyfield fight. He didn't care about boxing, was drinking and partying leading up to his fights. Evander was not in his prime but he was light years ahead of the guys Tyson was being put in with. Don King thought Evander was done and that Tyson could still go head hunting and win. Once Tyson realized he couldn't bully Evander the fight was pretty much over.

Holyfield was never 'done' at that point as people were thinking. He was simply messing up his steroid cycles before that time, after he lost to Bowe he was experimenting to try to get even bigger and stronger but he was screwing up dosages and stuff which is why he looked so bad in Bowe 3, Moorer 1 etc. Of course they could never admit it so they played the "heart problems" or STD cards which were phony lies. Once he fought Tyson everything was settled and there were no more drug screw ups, that's why he looked so great again 'all of a sudden'.

It's funny though that so many talk about it as it was kind of an expected result and when you think about it Holyfield has every chance of winning. but It was a massive upset at the time I believe some bookies had Holyfield a 25-1 underdog.

Holyfield was an absolute beast and Tyson was a bully. Most of the guys he fought were scared to death of him.

Both were a little past their prime and Holyfield was a much smarter and more versatile fighter, so his past prime was much better than Tyson's. Evander was a truly terrific fighter.

BOTH were on peds. Don't forget that Tyson admitted ped's use and how he avoided tests using a fake penis with clean urine. Mike used his whizzer so that he wouldn't get clocked using recreational drugs such as Mary Jane and The Devil's Dandruff before his fights. Mike's never mentioned PED's before and he's owned up to most things. Tyson's orime so was so brief it's hard to know how he fears against Evander. I actually think the pre-Don king Tyson, still trained by Rooney and still training fairly regularly had more heart than people give him credit for. the Tillis fight is a good example, Mike was dead exhausted in that fight and Tillis came down the lane hard at him, Mike bit down and fought back harder. I also seem to remember that one of the reasons Cus took Mike on was he put him in the ring with bobby Stewart who kind of beat Mike up a little bit but Mike kept on coming asking to go more rounds, despite getting bloodied up, and Cus liked that. the Mike that fought Spinks is a handful for anyone. Not saying he beats Evander but prime-for-prime is to me more of a pick 'em fight than some are suggesting.

He wasn't intimidated

Its a shame people just assume its all PED's. People here need to actually study boxing. Holyfield was in great shape, prepared well. Great game plan. He studied how Tyson had become predictable. How he stopped throwing combinations. Tyson neglected all the things that made him such an effective KO artist. When he is losing he becomes negative. Holyfields confidence got to Tyson. Like someone said, Holyfield was the real deal. And Tyson was not. After prison he was just a hype job.

Holyfield was a juicer and Tyson did years in prison.......

The common belief is that Mike Tyson was one of the greatest ever. He wasn't. Extremely exciting, absolutely! One of my faves? Fk yea! But not on the level of talent of a Holyfield.

Holyfield trained harder than any other heavyweight in the 90s. Tyson's work ethic had slowed down, and he got overwhelmed.

If Tyson had beaten Douglas I believe Holyfield would have beaten Tyson in his next fight and I'm a big Tyson fan. Holyfield was all wrong for Tyson.

Great gameplan, ring know-how, chin and determination. Holyfield was a better fighter, prime for prime too. ^^^^ this....

About the elbows and head butts? Y'all think this played a part? Tyson was frustrated and complained about it...

One point not yet made, was that by the time Tyson fought Evander he was a stationary target. Prime Tyson would set up his power with great head movement, but once he started to believe his own hype he stopped doing what made him great and became an easy target for a guy like Holyfield.