Are there any light heavies in history who potentially could've beaten Mike Tyson on June 27, 1988

Braddock? I think Spinks was a superior fighter to Braddock, but perhaps Braddock was more durable.

 

Much as I admire Tunney and Charles and as much as I might pick them against other bigger men, Tyson would be the wrong big man for either. I can't see either lasting too long. Same for Greb and Moore.

 

Fitzsimmons did KO a 300 pound fighter

 

Maybe Tyson slips and falls off the ring steps moments before the fight, injures his back and the opponent wins on disqualification.

 

Conn had actually picked Tyson to stop Spinks. Conn's and Tunney's movement may get them out of round 1 at least and maybe through 2 and 3. But Tyson gets to them both eventually and executes his furious judgment via KO. Charles, IMO, would just be too small and that's really all there is to it. Charles is the kind of smaller guy that can be pitted against some ATG modern sized heavies and have a reasonable chance at victory, at least in an upset. But those are bigger heavies who didn't have ATG punching power like say Ali or Holmes or heavies who may have had ATG punching power, but not the speed or skill to match like say Shavers or Foreman. While I'd favor Ali, Holmes and Foreman over Charles, I say that Charles could upset either of them. A young Tyson, who had the correct combination of size, speed, skill and punching power I think would be too much for Charles to overcome.

Now, if you could give Charles the same secret sauce that Holyfield got, give him some weight lifting, bulk him up to a solid, muscular 210-220 pounds while allowing him to retain his speed and skill and proportionately increasing his punching power and ability to take a punch to match his newfound weight, again like Holyfield, then I'd give this modern, up to date version of Charles as much of a chance to beat a 1988 Mike Tyson as I'd give a 1949 185 pound Charles to beat a 1960 Floyd Patterson, which is to say I'd give him a very good chance.

 

Captain Obvious says this is obvious!