Fury, Wilder, Ruiz and Joshua Would be interesting to throw Evander into that mix
The only one who would be a problem would be Fury. His sheer size and awkwardness would be difficult for most Heavys in history. (Certainly not his skill level, which is basic) But prime Holyfield would be able to win a dec against Fury. Both Wilder and Joshua Holyfield would stop if he's at or close to prime.
Because of his limited power, he´d have his hands full. What Holyfield had over this guys was speed, coordination, temper (might fire back) and grit. He didn´t have the punch qualities of a Ruiz or Wilder, which made AJ a hard fight for him. He´d have to work hard to win against all of them.
I only see him having problems with Fury. Beats the rest for sure. He would also beat Fury when at his best.
He'd beat Joshua and Wilder clearly. Ruiz might give him a good hard fight but Holyfield wins on points. Fury might nick a decision.
Fail drug tests. I think he looked to have the ability to neat any of the current crop, but I thinl he was using more than you could get away with now, and it borders on impossible to say how big a difference it'd make. Worth noting he lost to worse guys than some of the top ones now, so I don't think he'd end up as some unbeaten force. I think he gets overrated for being exciting fights too. I mean could we really invision none of the current fighters beating a past it Tyson and 1 out.of 3 with Bowe?
I don't think the current crop was capable of beating the versions of Riddick Bowe that Evander Holyfield faced nor are they capable of beating the version of Mike Tyson that Holyfield faced. Evander would be champion. Anything can happen in boxing but as of now I'd favor a prime Holyfield over anyone on the current heavyweight landscape.
Holyfield was great fighter who is a joy to watch, but he's overrated. He's quite inconsistent and I don't think he'd clear out the division in any era.
I guess it depends what sort of age we are talking. His longevity would bode well for him, but I still think he’d split fights with the best fighters of the era
On one hand one can say that in 1990 Holyfield was the undisputed Champion. And in 1999 Holyfield was unified champion and in between those years he beat Bowe, Tyson, Mercer, Moorer while picking up some losses along the way. Was he inconsistent? Yes. Did he fight up or down to his level of competition? Yes. But was he a stellar fighter? Absolutely, and short of being an all time great, it's awfully hard to beat him. I just don't see anyone in the current crop that would remain with their belt after they face Holyfield.