I learned long ago to never, ever count Holyfield out. He could look ordinary against mediocre opposition, but he rose to the occasion when he needed to. And you know, that head...not legal, but Holy made great use of illegal tactics when he needed to. It's perfectly possible that he opens cuts with that noggin of his. It was said above that he wasn't a big puncher, which is true, but his timing was excellent and he dropped or stopped or wobbled guys with great chins. His stamina, durability and overall boxing skills make him a handfull for anyone, provided he is on his game. This is a hard fight to pick. Vitali was usually so dominant-against mediocre to mostly merely decent opposition it must be noted-that he is difficult to rate. Either could win this. I favour Holyfield-slightly-at his best, to pull it out down the stretch and gut out a narrow decision.
Sorry , but Chisora ran him all over the ring. He beat his body from pillar to post. Vitali never clinched. Ever. So why you would mention it i do not know. Having to clinch means he hasn't the skills to compete against Holyfield.
I didn't include the Ibragimov and Valuev losses because Holy was getting long in the tooth by then. Please forgive the factual oversight.
I don't see this thing about Vitali clinching. Wlad was able to use the clinch as a weapon and basically make himself unbeatable against a smaller opponent who was unable to beat him to the punch. Vitali never shut an opponent down like that. Vitali relied on movement and range as a defence because that was his strength. Beyond that, Lewis shut down Holy with the clinch whenever he got close in the first, he was unable to do it in the second. If Vitali can keep Holy at range he wins the fight. But obviously Holy was very adept at fighting a bigger man as he showed in the rematches with Bowe and Vitali. I give Holy a very slight edge.
Holy beat Valuev at 46 and got robbed on German scorecards . Wlad and Vit never wanted to fight Valeuv. What more needs to be said.
Go back and revisit some of Holys fights in his prime. Look at his triple hammer piston like jab he used to get himself into close quarters which he then followed up with a crisp combination of hooks and defensive makeovers . Attacking on the move like that is a great skill . Heavy weights of today can't do that anymore. Vitali never faced a boxer remotely close to Holyfield in his entire life. Comeback Foreman was a much harder proposition than Vitali. Boxing is symmetry. Angles beat straight lines all day every day.
Anyone picking holy win by ko has some serious, Dino level delusions, even for classics. Realistically, holy one of the most overrated fighters of all time and has never shown he could beat someone as big and good as Vit. Arguably lost 3 times to mediocre Bowe and twice to Lewis. The only guys remotely in Vits size and skill range. Lewis Vit h2h is debatable, but Vits skill set was much more suited to dominating smaller fighters than Lewis. Vit either wins every round against Evan or stops him late.