You can only watch one of these Holyfield Fantasy matchups...

Honestly none of them.

 

Holy v Tyson 88. Everybody would be picking tyson, the buzz around him was massive, but i remember Ring magazine rating the contenders around that time and they were big on Holy being the only one with a prayer against Iron Mike. Its hard to exaggerate how big Tyson blew up in late 80s, he was all over the TV and everyone was saying he would rule for the foreseeable. He was Fighter of the year 86, Holy was for 87 and it would have been a massive fight in 88. Not a huge fan of the other options but Frazier Holy appeals too.

 

No, Holyfield didn't even have his 1st heavyweight fight until maybe mid to late 88 an had one of of his toughest fights of his career against a past prime Dokes who was on the comeback in 89. Theres no way in hell he would have been ready to fight Tyson in 88. The cancelled fight in 91 was the missed opportunity

 

Fair point, no-one was given much of a prayer vs Tyson at that time. Still its the one i would pick out of the choices given.

 

It's interesting that people want to watch a fight that already took place, and frankly, it wasn't great. Frankly, the Holyfield-Moorer, Bowe and Douglas-Tyson, and even Williams-Tyson fights were more pleasing to the eye. I'd like to see a fight between two factions, so Dempsey vs. Holyfield would be fine, but if I had to choose, I'd also like to see Tyson 88 vs. Holyfield 96.

 

I think a Holyfield vs Frazier bout with both fighters in peak form would be one hell of a battle!! ("Smokin Joe" eventually prevails but there would be a lot of similarities with the FOTC--Joe would definitely absorb some heavy punishment and would need to grind out a war of attrition.)