Holyfield all day long. Joshua would simply be too intimidated by a man able to consume more PEDs than him...
Holyfield did struggle with big heavies like Lewis and Bowe but Joshua isn't Lewis or even Bowe. Joshua doesn't know how to use his size like Lewis to manhandle and keep Holyfield off him and while like Bowe, Joshua is good inside, there's no way he can maintain the pace Bowe did or that Holyfield will bring. I think Joshua does well early but is broken down and stopped late.
Joshua would succumb to the pressure and mentally collapse after a few rounds, Holyfield takes advantage of that situation and knocks Joshua out...
Holyfield was used to defend punches with his head, and was target practice against both Lewis and Bowe, eating 350+ punches, and get gift decision, while being heavily outlanded. Holy is not Usyk who is no static target and its always on the move and you can't set up your punches. Also the best from AJ is yet to come, so let's what his absolutely best is and thwn compare prime vs prime. Currently AJ is on low so it's not fair to compare prime Holy vs him.
The best we have seen of Holyfield beats the best we’ve seen of AJ. Holyfield more than likely stops Joshua late on.
This would be a really good competitive fight, due to Holyfield's habit of going to war when he didn't need to. Real Deal stood up to punches from the likes of Foreman and Bowe, so he probably is durable enough to trade with AJ in spots, but Prime Holy's stamina would be the deciding factor. He'd be punching so much, so fast and in combos. AJ tires and gets stopped.
I'd bet on Holy to win 10 times out of 10, but in no way would it be a walk in the park. Holy went to war with Dokes, Cooper, Stewart and he'd probably take some serious damage from AJ before stopping him mid to late rounds.
If Holyfield stays on his toes and times his offense he could stop AJ late. It would still be really competitive though since Holyfield tended to abandon his defense. There would be moments where AJ would rock Holyfield and even fire off some combinations throughout the fight. I’d still pick Holyfield to win more often then not.
AJ either knocks him out cold in 6 rounds which is unlikely or Holyfield beats up him up down the stretch. AJ is too bad on the inside to deal with big daddy holyfield