There's been some discussion that Holyfield was sick or in recovery in the 3rd fight against Bowe, and that's why Evander lost. And he lost the first fight because he chose the wrong strategy, but learned after that fight. In the 2nd fight, some comments explained that Bowe was uncharacteristically unmotivated/ lazy during that one fight, which is why he didn't come out on top. The question is, would any version of Holyfield be able to beat a prime, focused Riddick Bowe?
I’m a big Evander fan and part of me says “Yes, if Evander fought to his strengths and was healthy, he would outsmart Bowe and win a close decision.”
But if Evander was really meant to get more than one victory over Bowe, it would have happened. Bowe is just too big for him, although Evander is without doubt the greater fighter imo. The irony is that Evander proved himself to be a real warrior in his losses to Bowe. Some wise man somewhere said, “In defeat, a man reveals himself.”