Tyson challenges Holyfield before going to jail

Discussion in 'Classic Boxing Forum' started by ikrasevic, May 29, 2026.


  1. ikrasevic

    ikrasevic War for Souls Full Member

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    Would belts end up in prison?
     
  2. AwardedSteak863

    AwardedSteak863 Boxing Addict Full Member

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    Naw, Holyfield beats that version of Tyson. Tyson was not the same guy in the 90s as he was in the 80's. Holyfield has always been a truth machine and the truth is, he had Tyson's number. At a young age, Tyson knew he couldn't intimidate Holyfield. In 96' al questions were answered.
     
  3. McGrain

    McGrain Diamond Dog Staff Member

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    Unless you're matching some busted version of Holyfield versus Mike, I'd always take Holyfield to get the win. Along with Tunney's obsession with Dempsey, I'd rate Holyfield's obsession with Mike as the deepest of all. He was utterly determined and it showed. Plus Mike's weaknesses just line up nicely with Holyfield's strengths.
     
  4. ikrasevic

    ikrasevic War for Souls Full Member

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    Even in 1988?
     
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  5. JackSilver

    JackSilver Boxing Addict Full Member

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    I’ve alway said that Tyson before he went to jail beats any version of Holyfield and also for that matter any version of lewis but the post jail one would lose to both of them
     
  6. AwardedSteak863

    AwardedSteak863 Boxing Addict Full Member

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    That would be the only time. I still wouldn't be surprised if Holyfield survived the early onslaught and broke Tyson down.
     
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  7. Boxed Ears

    Boxed Ears this my daddy's account (RIP daddy) Full Member

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    This will likely be viewed as some sort of Tyson fanboyism but it's my honest take-yes, I still favour Holyfield, but a different and completely justifiable referee and a younger Tyson with a less filled out Holyfield could absolutely change the outcome. I do believe Holyfield always believed he had Tyson, but I don't think it's necessarily true that it would go the same way. Also, I'm not big on the more weight = better for most of these matches, but at least Holyfield put on ATHLETIC weight. He didn't just bulk up with a vague notion of "throwing more weight around." His weight was actually functional
     
  8. ikrasevic

    ikrasevic War for Souls Full Member

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    this is better to hear than anything on the forum.

    Yes. Years after CW Holyfield only put on 15lbs for the Bowe 1 fight. Holyfield "bulk up" until the Bowe 2 fight.
     
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  9. Sangria

    Sangria You bleed like Mylee Full Member

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    Yes. Tyson beats Holyfield pre prison.
     
  10. Philosopher

    Philosopher Well-Known Member Full Member

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    Holyfield beats any version of Tyson any time in my opinion. Guy had his number and his attributes were all wrong for Mikey. 90s Mike had slowed down, 'prime' Mike was a force of nature but Holyfeild could take the heat then turn it up. He himself was a monster in his younger days and would fight at a pace with a volume of ferocity that would finish a fading Mike around the tenth.
     
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  11. ikrasevic

    ikrasevic War for Souls Full Member

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    Holyfield from which fight would he set against 1988 Mike; which Holyfield do you think has the best chance (but you only have 1 choice)?
     
    Last edited: May 31, 2026
  12. Saintpat

    Saintpat Obsessed with Boxing Full Member

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    Buster Douglas manhandled pre-prison Tyson.

    Holy would also.
     
  13. ikrasevic

    ikrasevic War for Souls Full Member

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    I was thinking of the situation after that.
    Douglas beat Tyson, Holyfield beat Douglas, and now Tyson is the challenger.
     
  14. Saintpat

    Saintpat Obsessed with Boxing Full Member

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    Doesn’t change my answer.

    We can’t pretend pre-prison Tyson was unbeatable when he got KTFO by Big Bus.
     
  15. Philosopher

    Philosopher Well-Known Member Full Member

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    I don't think you can pick a version from a single fight as the fighter was training to fight a specific fighter. The Holyfield who manhandled and bullied Tyson twice in the 90s fought that way because of what Tyson's attributes were then. I don't think he can fight that way against the force of nature Tyson was in '88. Evander was still raw in the late eighties but look at the wars he was in already, Qawi at CW and Dokes being standouts. I see a version of that raw obstinate, obdurate, driven, fast version matching peak Tyson's intensity and taking over late. Whilst it is true Evander never fought anyone with peak Mike's incandescent ferocity, peak Mike never fought anyone with Evander's resilience and heart. Mike prepared to KO people, Evander prepared for war.