Which slick boxer has the best chance against the great Evander 'Real Deal' Holyfield. He was a warrior who did his best against flat-footed opponents who stood in front of him or came at him. He struggled against technical big men with power (Bowe, Lewis & Foreman to some extent). But the main style I think he struggled with was the slick boxer type as his fights against slick boxers Holmes, Byrd, Toney & Donald were some of his worst performances.
I think every one of those fights would be close either way. Holyfield probably beats at least half of them while potentially losing on close points to the others. You might also see mixed results if he fights each one multiple times. picked Ezzard Charles as the favorite of all those
It's a tough call. Maybe I'm crazy, but I'm inclined to go with Jack Johnson here. He's got appreciable size and robustness. His style just may be something so different to what Holyfield is used to, that it may upset his timing and rhythm. Johnson may provide a look Holyfield hasn't seen before. (In fairness, the opposite probably applies.) Johnson also had amazing confidence in himself. I think he'd be smart enough to figure out certain patterns in the fight and adjust. His awkward style just might cause issues. Jersey Joe might be next. Super tricky and awkward. After that, I don't think anyone on the list is particularly noteworthy. They're not especially awkward or tricky. What are they doing that Holyfield didn't already deal with before? Good boxers all yes, but nothing Holyfield couldn't handle. Just very good, but mostly conventional fighters. I think you'd need more than that to beat Holyfield.
All at once? I pick the slick fighters. If it's one at a time then I pick Tunney because apparently he gets two chances
Its a good thought provoking thread and I'm enjoying it but I'd respectfully as a huge EH fan argue Holyfield didn't actually struggle much with slick boxers at all . The Toney/Byrd/Donald losses came when Holy was totally gone (injury ravaged and unable to fight more than 30 seconds and 40 plus. Of the poll I reckon Jack johnson and a prime Young may just beat him
Assuming that Jack Johnson gets to see films of Holyfield first, I give him the best chance against Evander.
Charles is the only one I'd slightly favor to beat Holyfield. Haven't seen enough Jack Johnson to say either way
Charles, Jimmy Young...Johnson sure had a good chance. Prime Holmes would have been very interesting, especially the 78 Shavers I guy. It might have ended up a split decision. Past Norton, though, Holmes would have used his greater stepping in power to probably run away with the decision imo. Not sure he could have stopped Holy. Not sure at all.