These two had bad chemistry which had been simmering since their amateur days & their infamous sparring session back in the early ‘80s.
However, Holyfield fought dirty in both fights, not just the second fight. But because of what transpired in the rematch & specifically Tyson’s notorious retaliatory bite— Holyfield’s shady & clandestine tactics received more press coverage after the second fight. In other words did Holyfield deliberately provoke such an outrageous response from Tyson ?
But in general, Holyfield has always pushed the Queensbury rules to breaking point. Against Tyson, he simply upped the ante because of their previous bad blood & was more trigger happy with his covert head use. He also wanted to upstage Tyson on the inside & make a pugilistic statement along the lines that his all-round style was Tyson’s kyptonite.
Something else that Holyfield has alluded to after the fact is that he wanted to get some payback, for the slow beating that Tyson had put on Tyrell Biggs in 1987. It is a fairly well known fact that Tyson carried Biggs for two extra rounds by solely targeting his body, when he could have finished him off in round 5.
Anyone who has seen the Biggs fight can see that Tyson literally made a grown man cry in the ring -through constant body punching. Tyson played with Biggs, visibly enjoyed his work & gloated in his victory during the post fight interview. Tyson even spoke of Biggs like a trophy victim.
Biggs (far left) was Holyfield’s friend & amateur teammate from the highly touted US 1984 Olympic team. So needless to say, Holyfield didn’t like to see his friend treated in this manner & therefore wanted to give Tyson “a taste of his own medicine.”