What if Harry Greb fought Jack Dempsey for the Heavyweight title? Could he have won, and thus join Fitzsimmons and Jones in the list of fighters who won titles from MW to HW?
If he had gotten the 10 round distance that Tunney received, he would have been heavyweight champion of the world.
No one is a bigger fan of Harry Greb than I, but no way Harry Greb survives a prime Dempsey in full attack mode...Sparring sessions mean zilch. The greatest fighters I've seen ringside ,have been outworked in training sessions...Of course Harry Greb during his amazing career defied normality, but not against a fast 20 pound heavier tiger that was Jack Dempsey...
Out of everyone Harry Greb fought, Jack Dempsey is gonna be the guy to put the former away? I'm not buying it. Greb feasted on the same heavyweights Dempsey fought, and then some. He defeated every heavyweight he ever stepped into the ring with, including Dempsey's sparring partners (Renault, Malone, Monoghan). And Dempsey knocks Greb out within 15? Dempsey had a good hooks but its not like his power leaps out at upu historically like Moore's or Shavers. Greb was knocked out once in 299 fights and was green when it happened. He took countless heavy hitter's best shots. The dude ducks Greb for 2-3 years and he's supposed to magically handily defeat him? It doesn't work that way. You don't duck someone, **** your pants whenever you hear their name, and then step into the ring and it all goes away and you destroy the greatest fighter of all time. **** that. And, yes, sparring sessions aren't the end all be all, but damn it's real nice for that to be only 6 times the two men stepped into the ring together and it not mean anything. Greb battered Dempsey; busted his eye, split his tongue, left him gasping for air. Does that mean everything? No, but it's still more than Dempsey ever did to Greb. Greb trounces Dempsey, and I'm sure of it. Dempsey's nothing special compared to Greb and the top men he defeated. Walker, Tunney, Gibbons bros, Dempsey isn't at that level. Yes, stylistically he's much different than those men but history doesn't work that way. Dempsey didn't have that special something like these men did. That special something that you can't really explain but you know when you see it. He's just not great not great like these men were. He won't be the one man to clearly handle the personification of perpetual motion that is Harry Greb.
One of two things happens. Either: A. Dempsey catches up with him and knocks him sensless, then modern fans berate Dempsey for fighting a middleweight. Grebs p4p status is still secure. or B. Dempsey gets outpointed, at considerable detriment to his own reputation, and Greb is the consensus p4p #1.
I think Greb's only chance is if he fights a similar Dempsey to the one Tunney fought, coming off the 3 year lay off. I'd take any other version of Jack with the utmost confidence.
For whatever it is worth, you could probable have found more people at the time willing to pick Greb over Dempsey, than Wills.
Greb may well have won, he had the speed and probably the defense and height/range to outbox Dempsey. GReb would certainly by far the best boxer Dempsey had been in with pre-Tunney and maybe better than Tunney anyway circa 1919