What if? Tyson had fought Holyfield before Douglas?

OK. So Teddy doesn't count. It still stands. Tyson was scared ****

It's out there. You look it up.

 

If Tyson was in a better place mentally it might have helped him against Evander. Then again he’d also be in there with a better opponent than Douglas. Regardless of who would have won this would have been a war and one that the public was deprived of.

 

Good question — there’s a bit of myth around this.

Mike Tyson and Evander Holyfield were both on the rise in the 1980s, but they never fought then. The idea that Tyson was “scared” of Holyfield mostly comes from hindsight, because their first actual fight wasn’t until 1996, well after Tyson’s prison sentence.

Here’s the breakdown:

• Late 1980s: Tyson was the undisputed heavyweight champion (1986–1990). Holyfield was moving up from cruiserweight, becoming the undisputed champ there in 1988 before transitioning to heavyweight.
  
  
• Fight discussions: Don King and others floated Tyson–Holyfield in the late ’80s/early ’90s. But Tyson’s management steered him into other big-money defenses (e.g., Frank Bruno, Carl Williams).
  
  
• Reasons it didn’t happen:
  
  • Holyfield wasn’t yet established at heavyweight until 1989–1990.
    
    
  • Tyson’s camp wanted him to keep knocking over marketable heavyweights rather than risk him against a fresh, hungry challenger.
    
    
  • When Tyson lost to Buster Douglas in 1990, Holyfield stepped in and beat Douglas for the title.
    
• Fear factor: There’s no credible evidence Tyson was “scared.” Tyson himself has admitted he respected Holyfield’s toughness and discipline. Some writers argue Tyson’s team may have been cautious, but that’s different from Tyson himself being afraid.
  

So: Tyson wasn’t scared, but business, timing, and his legal troubles kept the fight from happening in the 1980s.

Do you want me to pull up what Tyson and Holyfield themselves have said about this period?

 

I favor Mike Tyson, but a Holyfield win is not out of the question.

 

Tyson does better against Holyfield then he did in the real fights. Whether thats enough to win he was never better prepared to deal with someone like Holyfield.

Tyson was a second away from getting the comeback victory against Douglas which would have been the only comeback victory of his career.

 

The Real Deal was all wrong for Mike. Style wise Evander had Mike's number. He had Buster's number too, what a coincidence. I wish Mike didn't ruin the PPV by going ballistic, it would have been a hell of a fight, it was really heating up.

 

You keep telling yourself that Mike if it helps you sleep at night.

 

Ah, Chat GPT, welcome to the group!

 

How do you know that?

Maybe he was also afraid of Henry Tillman and Tyrell Briggs, who harassed him during sparring sessions.

Why didn't Holyfield ask the WBA, WBC, or IBF to make him an official challenger, which he was entitled to as a lower-division champion in EACH of those federations?

Instead, instead of trying to fight for his legitimate challenger rights, in 1990 Holyfield fought to strip Tyson of those rights. He sued the WBC, which ordered him to fight Mike Tyson instead of George Foreman.

Unbelievable !!
We have irrefutable evidence that Evander wanted to postpone the Tyson fight as much as possible, yet Tyson has been accused for years of being afraid of Holyfield.

https://www.deseret.com/1990/12/12/18895705/tyson-climbs-into-legal-ring-with-holyfield/

 

There has to be more to the story as Evanders balls are too big for his brain unfortunatly and he is pretty dumb. I think he would want to fight Mike.
If you saw his face in the Douglas/Tyson fight ,he was pissed at the fact Mike was Losing

 

Almost guaranteed.

 

Mike ‘knew’ he would beat Buster Douglas, too — we saw how that turned out.

I agree with your assessment. I think Evander had Mike’s number mentally and would always have an edge. Buster wasn’t scared of Mike and steamrolled him.

Holyfield wasn’t scare of Mike either. He beat him up when they sparred in the Olympic training camp (Pat Nappi, the Olympic coach, ended the session when Holy trapped Mike in a corner and Tyson couldn’t get out).

There’s also the pool room incident. They had a pool table for the boxers. If you lost, you stepped aside and someone else stepped in for the next game. Tyson lost. He refused to give up the pool cue, being the bully and figuring nobody could make him give up his spot. Evander walked right up to him and took the cue out of his hand and Mike stalked off from the room and wasn’t seen again that night.

Keep this in mind: At the time, Evander was a light heavyweight and Tyson was a heavyweight.

Mike was always going to be Evander’s *****.

 

But was Mike a teenager?

 

He was a heavyweight. Evander was a light heavy.

Evander was just a boy himself at 21. Hardly a grizzled, full-blown man.

And guess what — no matter when they fought, Holy was going to be 4 years older than Mike. So what?

Mike was sparring with truly grown men — professionals — when he was young. Now all of a sudden you want to act like he was a toddler because Holyfield got the better of him, lol.

Evander was more man than Mike at any age. He probably started shaving when he was 4 years old.

 

When they fought I don’t think it really represented either fighter sufficiently… Prime Holyfield didn’t fight the way he did in 96 and neither did Tyson. My 0.2$ Tyson wins.