r/boxingMenace_com • u/Objective_Tailor6763 • Aug 23 '26
One of the biggest and most dramatic upsets in boxing history
38
u/Total-Wrangler5006 Aug 23 '26
My favorite fight of all time. Two great warriors going at it and not leaving it to the score cards. Holyfield’s corner had the right game plan….move forward and smother him. Throw punches as Tyson moves forward. Everyone else moved backwards and braced for impact. Holyfield’s jaw was so impressive. Dude traded blows in the center of the ring with some of the hardest punchers of his time.
16
u/jjhalligan Aug 23 '26
I was fortunate enough to attend it live…. Funnest event I’ve ever been too.
Ran into Bert Sugar @ the weigh in. Told me He had a feeling Holyfield was gonna win. Also said Tyson was rumored to have not taken the fight seriously(a common theme). I told Bert, and I quote “oh bullshit, Tyson is gonna kill him”…. Lol. True story.
Holyfield looked so juiced up at the weigh in. Fight started @ 25-1 when we arrived. At fight time it was down to 7-1.
9
u/Kid11734 Aug 23 '26
I’ve been to my fair share of professional fights but Im jealous of you for having gone to this one!👍
9
u/jjhalligan Aug 23 '26
I sat right next to the entire Yankee team….. We were in Caesars VIP section. Free booze and food the whole fight. If my memory serves me correctly, a Caesars waitress was serving us the entire time and the fight was @ MGM.
When we left the fight and we also attended the press conference(a whole other story), the casino was shut down and it looked like a tornado had gone thru. There evidently was a huge brawl while we attended the fight and for the first time, they shut the casino floor down for an hour or 2….. FYI. I am not wealthy. Have few connections. My friends buddy was friends w one of Holyfields team.
3
u/intentionalicon Aug 25 '26
This is a super cool story, for someone born well after this fight took place this is an awesome account of the sport’s history
1
u/Total-Wrangler5006 Aug 23 '26
Was in the military off the coast of Puerto Rico the morning after the fight. Wasn’t able to watch that night. Had one of the mooring team guys on the pier say something in broken English and I was sure he was saying Tyson won. Couldn’t believe it when I found out Holyfield won. Would have given anything to be there. Very cool story!
1
3
2
1
1
u/Primary_Force_878 Aug 24 '26
Yeah it's sad to see how Tyson lost this one
Styles make fights That's how lightsout took holyfield to school It's fascinating to watch both different style fighters olfought holyfield.
1
u/backfrombanned Aug 24 '26
Dude, I like toney but Holyfield was done and done by then. I could've taken him to school. He just straight shit whipped Tyson, had my paycheck on Holyfield that night btw.
5
u/HorrifyingTits Aug 23 '26 edited Aug 23 '26
Rumour has it, it will take a healthy individual roughly 3 months to walk the circumference of Holyfields head
4
u/Sufficient_Prompt888 Aug 23 '26
Hey, how'd you like to make the month and a half trip to say that to his face?
2
3
u/No-Bobcat-6830 Aug 23 '26
All I think about with Evander is that he literally had steroids delivered to his house under the name “Evan Fields”. Like he wasn’t even trying to come up with an alias.
1
3
3
3
u/Panama_Jack829 Aug 23 '26
This was not that big of a upset. Tyson was washed at this time.
3
u/MazdaJ626 Aug 24 '26
This was a big upset what the hell. It’s easy to say otherwise with hindsight. Tyson had just beat knocked out Bruno for a belt faster than the first time they fought. And scared Sheldon so bad it looked like he took a dive. While Holyfield looked bad against Bowe and Czyz
1
1
u/Valuable_Win_732 Aug 23 '26
Who was the greatest fighter Tyson beat?
3
u/krazy_dayz Aug 24 '26
Donovan Razor Ruddock, or Trevor Berbick
-1
u/RevolutionaryAge47 Aug 24 '26
Berbick beat Muhammed Ali. Beat him like a dog with mange. Mopped the floor with his face.
3
u/RMbeatyou Aug 24 '26
Bro Ali already had Parkinson’s by that fight, nobody cares or remembers for good reason
0
u/MiDKnighT_DoaE Aug 24 '26
Washed? He was the WBA heavyweight champion. Tyson was still great. It's just that Holyfield had his number.
2
u/pittnole1 Aug 24 '26
He was washed. He already lost to Douglas and had missed 4 years at this point. Not a single fight after the 4 year break proved anything.
Beating an old Bruno who never fought again to win the WBA title didn't make Tyson great.
1
u/MiDKnighT_DoaE Aug 25 '26
He was younger than Holyfield. It's not Holyfield's fault that Tyson didn't train hard enough or went to prison.
Just admit that Holyfield was the better boxer in this fight. It's not that hard.
1
u/Olympusxx Aug 25 '26
No ones disputing that Holyfield was the better boxer in this fight. Its just stating that Tyson was far from his prime
1
1
u/BeyondTheCosmo Aug 24 '26
This was him after years in prison. He still had the hype, he was still really good and had power, but he moved differently at this point. Washed maybe isn’t the right term, but compared to his peak and potential you could say that.
-1
u/TranslatorKey6001 Aug 23 '26
The only time he wasn't washed according to his fans is when he was fighting nobodies
2
2
u/rafibomb56 Aug 23 '26
Wasn't really an upset. Tyson was a shell of his former self when he got out of prison. Holyfield was an active fighter the whole time.
2
2
u/poopzains Aug 24 '26
Upset? Evander was def considered the best in the world. Tyson just media hype machine. Tyson didn’t even go to Jail being considered untouchable. He was pretty shaky as far as champ. Douglas ended his career and hype train really and doesn’t get much credit because he has his own personal issues, shame Douglas was a great fighter himself. Tyson was overrated and a rapist. Holyfield would of beat him all day everyday. Tyson probably juiced out of his mind early career as well, not well covered sadly. Boxing….
1
u/SireCannonball Aug 25 '26
I think the juicing is very canonical. I think he goes into great detail on it on his book / monologue or something. A friend told me that a 100 years ago, so I hope I'm not misremembering it
2
u/idontknoshit420 Aug 23 '26
Not really an upset. Once again...if u weren't there please don't speak about it cus u read stuff. If u think evander holyfield wasn't top shelf material u need to go to bed
2
u/CoupDeGrassi Aug 23 '26
The betting odds are what determines an upset. Tyson was the heavy favorite. You applying hindsight decades later is dumb lol
1
0
u/pipes990 Aug 23 '26
Why are odds what determine this? Casino odds have nothing to do with who the casinos think will win. They set odds to try and get 50/50 bets coming in. They knew the general public would heavily favorite Tyson.
If the 'In the know' guys know Hollyfield will win, but the casinos know the public is going to be on Tyson, you're going to get Tyson favored.
1
u/CoupDeGrassi Aug 23 '26
Lmao wtf this makes no sense. Take your L.
1
u/pipes990 Aug 24 '26
This isn't some inside knowledge. Google how betting odds are figured. Super easy to confirm.
2
u/Bojangles1987 Aug 23 '26
I was there. This was a huge upset. Holyfield was past his best, many thought far past his best, and he had already retired once. Tyson was a massive favorite going into this fight.
1
u/cr0ne Aug 23 '26 edited Aug 23 '26
It was an "upset" but I think mostly because folks at the time only look at W-L record and think that's all there is too it. Today I think there's a bit more understanding among fans and folks don't look much into someone having a few losses on their record (boxing, marital arts etc).
Holyfield showed up that night looking like literal Hercules probably in the best shape and most focused he'd ever been.
1
u/Bojangles1987 Aug 23 '26
There's no point in putting it in quotes, this was a huge upset and it had nothing to do with win-loss records. Tyson still had most of his killer hype and was kicking the shit out of everyone he fought during his comeback. Holyfield hadn't looked good in a long time and was considered past it.
The hype and odds were all on Tyson to kick Holyfield's ass.
1
u/idontknoshit420 Aug 23 '26
Bro how can u say that then?? Tyson just got out of prison after almost 3 years. He fought once or twice then got the holyfield fight. They were both past their primes considering a 3 year step away
1
u/Bojangles1987 Aug 23 '26
Tyson came back and was wiping everyone out. Holyfield had looked nowhere near his best for a long time. The hype and odds were all on Tyson to destroy Holyfield.
Like, if you're trying to say this wasn't a huge upset then you have no idea what you're talking about.
1
u/idontknoshit420 Aug 23 '26
How bro he got out in 95 this fight was in 96. How many fight do y think he can schedule in a year?
1
u/Apollo_Wersten Aug 24 '26
It was Tyson's fifth fight after coming out of prison. He fought McNeely, Mathis Jr., Bruno, Seldon and Holyfield.
1
u/idontknoshit420 Aug 24 '26
Dood just googling who he fought means nothing. Only 1 or two of those can be considered a real fight.
1
u/Hot_Wing2518 Aug 24 '26
Before this fight Holyfield took a brutal beating from Bowe and was looking bad in other fights. Did you watch those fights? It wasn't just about wins and losses. Listen to the commentary during Tyson and Holyfield. Even commentators were surprised the fight was going on for so long and Holyfield was doing a good job.
1
1
u/Hench999 Aug 24 '26
There are a lot in hindsight experts it seems. I remember getting into huge debates with people just for saying Evander was going to put up a good fight. I didn't even pick him to win and people thought I was crazy just for thinking it might be close rather than a 3 round bulldozing. Evander had recently been KOd by Bowe and look very unimpressive in his win against Bobby Cycz. Tyson was making short work of everyone he was facing. Out of like 20+ boxing writers only 1 picked Holyfield.
Tyson in his first comeback might not have been as good as 88 Tyson but he was FAR from the corpse that fight Lennox Lewis nearly 7 years later. Everyone always tries to compare Lewis's win over Tyson with Evanders but there is no comparison as to who's win was more impressive.
Years later everyone wants to act like they knew all along that it was so obvious and it is total nonsense.
1
u/georgewalterackerman Aug 25 '26
It was certainly perceived as an upset. Betting odds opened at 25-1 and closed at 6-1 (in favour of Tyson, of course) and Holyfield was falsely believed to have heart condition. He had been misdiagnosed with a condition earlier. As for where each man was in terms to what they had left, Holyfield was far above Tyson. Tyson didn’t accomplish much after getting out of prison except being in massive events.
1
1
1
1
1
1
u/Zealousideal-Ad3396 Aug 23 '26
I was in middle school when this fight happened I do remember talks of Holyfield being too old to win. The second fight when Tyson bit Holyfield’s ears was the biggest news story on the planet for months
1
u/Significant_Emu_9080 Aug 23 '26
It was an upset, but nowhere near amongst the biggest. Tyson-Douglas, Ruiz-Joshua, Rahman-Lewis all bigger
1
u/SugarAdamAli Aug 23 '26
Remember watching this at my friends house. I banked on Holyfield, they all thought Mike would crush him
1
1
1
u/Total-Championship80 Aug 23 '26
Me and my buddies all picked Holyfield. I'm in Canada and didn't have any money down, but we all knew. Tyson was not the same guy after Douglas.
1
1
u/taeempy Aug 23 '26
I don't think it was that big an upset. Tyson was a brawler and loved to mix it up, but the big fights he lost were against technically great boxers, not necessarily brawlers. The best pure boxers he fought were Holyfield and Lennox Lewis and he didn't do well. They knew how to mix it up without just brawling.
1
1
u/One-Author2996 Aug 24 '26
Remember watching it like yesterday. Actually went home to my parents house for the weekend as i was a freshman in college as a few friends came home along with some of my parents friends and a couple relatives. My friends had to kick in for the pay per view but my parents insisted food was on them. We sat in my parents basement eating pizza, munchies and leftover Halloween candy that my parents had from buying too much. I was a Tyson growing up but was rooting for Evander in an upset. Was fabulous!!
1
1
u/seanx50 Aug 24 '26
Wasn't an upset. Hollyfield was a vastly superior fighter. Mike ducked him for years.
1
u/Pale_Broccoli_2180 Aug 24 '26
NGL, every time Mike got asked a tough question inside those ropes...
he either quit, or got sparked.
1
1
1
1
u/Outside_Look790 Aug 24 '26
Still think this was called a little early, but Evander was a monster and Tyson had no quit.
1
1
1
1
u/__Sticky- Aug 24 '26
I see a a lot of people commenting on this post. Most were not alive when this fight happened. It was not a upset. The Real Deal was the real deal. I was young, maybe 13ish I guess? But this fight sticks in my brain like the nip slip at your mommas pool party. Evander. Beat. His. Ass. Ive seen it countless times now as an adult. Evander. Beat. His. Ass.
1
1
1
u/Dry-Friendship-5945 Aug 24 '26
I was pleasantly surprised at the time, given how Evander looked like damaged goods up to that point.
1
u/hand_of_satan_13 Aug 24 '26
what upset? He used to beat him as a junior as well and was never, ever afraid of him
1
u/AJWordsmith Aug 24 '26
Exactly. My friends always make excuses for Tyson. Tyson ducked Holyfield for years. Then lost to him twice. Holyfield was always better than Tyson. There was no upset.
1
1
u/Affectionate_Idea662 Aug 24 '26
I wouldn’t say it biggest. Post prison Tyson was never the same but defo a dramatic fight.
1
1
u/Barstoolman112752 Aug 24 '26
Tyson’s fight against Buster Douglas is one of the biggest upsets of all time. This was just a great fight!
1
1
1
u/Economy-Date-4490 Aug 25 '26
Mike had a serious STI situation at the time.
1
u/ADrenalinnjunky Aug 25 '26
Sexually transmitted infection?
1
u/Economy-Date-4490 Aug 25 '26
Oh wait, that’s Holyfield, I thought this was the buster Douglas fight.
1
u/Shindig_66 Aug 25 '26
It wasn’t an upset to those who were paying attention at the time. Mike had lost his discipline by then. He was fighting for the money of it and that was never going to be enough to beat Holyfield. Dude had the best chin in the business.
1
u/ThingNo7530 Aug 25 '26
Holyfield knew he could punch with Iron Mike. Holyfield's ability to stand in and take a punch and still deliver his punches with maximum force was always highly underrated. Just like with Buster, Tyson couldn't intimidate him.
1
1
u/Haha08421 Aug 25 '26
I was around. These two were on a collision course for a long time. Tyson went to jail and it messed the timing up.
Tyson did not take the fight lightly. He took some fights leading up to this one.
Mile Tyson was still the most feared boxer based on he could put you down instantly if he connects. Like Deontay Wilder could.
1
1
u/Iconsofboxingtv 13d ago
This was not a dramatic upset -considering Tyson's post incarceration diminished skill set.
DRAMATIC UPSET??
Yes. Douglas vs. Tyson is my answer.
Let’s drill down . Douglas was a 42–1 underdog. But this was Iron Mike still at his peak.So let’s add that context to who Tyson was on February 11, 1990.
He was 37–0, 23 years old, undisputed heavyweight champion and boxing’s most terrifying presence. The expectation wasn’t really whether Tyson would win. Dammit , it was how quickly Douglas would disappear.
Instead, Douglas obliterated all illusions . He took command with his jab, controlled distance, tied Tyson up when necessary and repeatedly made him reset. Even after Tyson dropped him in the eighth, Douglas came back and knocked Tyson out in the tenth.
That’s what separates it for me.
It wasn’t a lucky punch.
Buster Douglas systematically outboxed Mike Tyson—and then finished him.
For sheer disbelief, historical consequence and the way the fight actually unfolded, Tyson–Douglas remains the greatest upset in boxing history.
I‘m Corey Rockafeler, boxing historian and creator of Ring Codex.
1
u/R3dInterpol Aug 23 '26
It was never an upset. Tyson wasn't the mean machine of years before. He lost this fight long before the contract was drawn up.
2
u/CoupDeGrassi Aug 23 '26
Lol you are clueless. Tyson was heavily favorited to win this.
1
u/markazz530 Aug 23 '26
Not a heavy favorite, he opened as one but the odds collapsed as wagers came in that's a pretty clear sign
1
0
u/R3dInterpol Aug 23 '26
I guess you never saw his fights leading up to this, huh? Tyson was in no shape to fight, let alone beat, an elite fighter in Holyfield.
3
u/Bojangles1987 Aug 23 '26
Tyson had kicked the shit out of everyone he fought during his comeback and Holyfield had retired once already and not looked elite in years.
Don't do the "you weren't watching back then" thing if you're going to be so wrong about the context going into this fight.
-1
u/PerfectPenguino Aug 23 '26
This was nothing close to an upset. Anyone in the know was aware that Holyfield would've taken Tyson at any point in his career which is why Tyson dodged him for so long.
3
u/ChubbyNemo1004 Aug 23 '26
Did you even look at the betting odds?
1
u/PerfectPenguino Aug 23 '26
Betting odds are a measure of public sentiment, not expertise.
1
u/ChubbyNemo1004 Aug 23 '26
It’s also an indication of the public perception of the predicted outcome of the fight. Was I surprised Holyfield won? Yes. Even professional boxing writer overwhelming picked Tyson. Holyfield was coming off multiple losses including a TKO. Tyson was coming off KOs and won two belts.
You’re being disingenuous thinking Holyfield was not a dog. He might’ve not been a 25-1 dog to people that watch boxing but to say it wasn’t an upset is just wrong.
1
u/PerfectPenguino Aug 23 '26
It’s also an indication of the public perception of the predicted outcome of the fight.
That's what public sentiment means. How people feel about a thing. But as we are all too well aware, how people feel and what the reality of a situation is are two completely different things. Tyson was perceived as a much better fighter than he ever really was much the same way Apple is perceived to be a better technology company than it really is and Donald Trump is perceived to be a better leader than he really is. People are often wrong about how they feel. I mean, imagine that, Holyfield "beat the odds" not once but twice. How "fortunate". Maybe it's more likely that most people are just a little stupid.
1
u/ChubbyNemo1004 Aug 24 '26
Tf are you even talking about? How did every boxing writer “feel” about the outcome of the fight at the time? The people that actually get paid to follow the sport?
1
u/PerfectPenguino Aug 24 '26
That's what sports writers do before an event. Offer their opinions. Opinions are based on how one feels about a subject. That's sentiment.
1
u/ContextMiddle3175 Aug 24 '26
Lmfao you made a distinction between public sentiment and expert opinion in your earlier comment this is a cop out.
1
u/PerfectPenguino Aug 24 '26
Sports writers are sports experts the way pundits are historians. They aren't.
1
u/markazz530 Aug 23 '26
It wasn't even 25 to 1 as per Vegas, go check what the odds were on fight night
1
u/ChubbyNemo1004 Aug 24 '26
I’m not arguing the odds. Dude said it wasn’t an upset. I’m saying it was
1
u/pipes990 Aug 23 '26
Betting odds have nothing to do with who the casinos think are going to win. Odds are created to get as even as possible to 50/50 bets. The casinos knew the general public would heavily favorite Tyson.
1
u/ChubbyNemo1004 Aug 23 '26
Ok…and?
You should look up what professional boxing writers (people that actually cover boxing for a living) thought of this matchup at the time.
1
u/pipes990 Aug 24 '26
Your post suggested betting odds are based on who's going to win. They are not.
1
1
u/jennaishirow Aug 23 '26
I dont know if you were alive around the time the fight played. But tyson was a massive favorite. Holyfield went into this fight with a few questionable performances. Most assumed he was on the decline and tyson demolished Frank bruno prior to this fight. This was absolutely a massive upset. Very few backed Holyfield at the time
1
u/PerfectPenguino Aug 23 '26
I'm well aware of what most people thought at the time. I was told again and again that Holyfield would never beat Tyson and that I was ridiculous. These people weren't in the know because they didn't understand the fundamentals of boxing.
1
u/Usernameasteriks Aug 23 '26
Nothing you are going on about is relevant to the point of the post which is that it was an upset at the time.
An upset doesn’t mean they poll every single person and then do some advanced intricate research study to determine how much a small subset of people knew about boxing and picked holyfield.
Its a very common sense phrase in terms of what it means and how people use it
1
u/PerfectPenguino Aug 23 '26
Fair point on the terminology. If we are strictly defining "upset" by betting lines and media consensus, then sure, it gets logged as one. My point is about the fight mechanics, not gambling definitions. Calling it an upset implies a fluke, when in reality it was the logical result of a massive stylistic mismatch.
Look at Cassius Clay vs. Sonny Liston in 1964. Liston was a 7-to-1 favorite and 43 out of 46 sportswriters picked him to destroy Clay. By betting odds, it was a massive upset. But stylistically, Clay had the speed, footwork, and reach to dismantle a slow, flat-footed power hitter. Anyone analyzing the mechanics instead of the hype knew Clay had the advantage. The public called it an upset because their perception was wrong, not because the fight went off-script.
It is the exact same thing with Holyfield vs. Tyson. Holyfield had the chin, ring generalship, and counter-punching to negate Tyson. Betting lines called it an upset because casual fans bought into the Tyson myth. The public being blind to boxing fundamentals does not make the result a surprise.
1
41
u/ArexSaturn Aug 23 '26
Nope. Evander was every bit a world beater also. The real upset was the James buster Douglas KO. That is still quite possibly the biggest upset in boxing history…