1992 Razor Ruddock Michael Grant Hasim Rahman 1998/99 Evander Holyfield 2002 Mike Tyson Frank Bruno 1993 Tony Tucker Tommy Morrison David Tua Shannon Briggs Ray Mercer Gary Mason and finally 2003 Vitali Klitchsko Could Willard use his size strength and skill to defeat every man on this ledger?
Holyfield and Klitschko start as clear favorites over him. I am guessing that he wins some and loses some against the rest. I would make him a clear favorite over Grant, Bruno, Morrison, and Mason.
They all beat him, most embarrassingly so. But I actually do have a reservation about 2002 Tyson. He was on the verge of really falling off the cliff, coke-addled, boozer, over a decade past his prime.
I don't really know the attributes of many of the opponents put forward, but in a fight scheduled for 45 rounds, as I remember the Willard-Johnson fight was, I give Willard a chance against some of those listed, i. e., Shannon Briggs and Frank Bruno who I remember seeing, if the fight goes longer than 20 rounds. Don't know much about the other guys. Under modern 12- or 15-round bouts, I don't see Willard doing much against modern heavyweights. He is an interesting historical curiosity, however.
Briggs would lose. Tyson 02 and Morrison have chance to gas out late if Willard could absorb a beaten. but if Dempsey at 188 got him out i doubt the bigger guys couldn't do the same.
I would consider him an underdog against all of them. He would have had the best chances to beat 2002 version of Tyson out of these guys in my opinion. 2002 version of Tyson had beyond awful stamina. In 2002 Tyson was slightly better than he was in 2005, but Willard was also better than Kevin McBride.
I honestly think Willard would struggle against Tye Fields. He could win if he dragged the fight past 25 rounds like he did with Johnson.