I don't know about these hypothetical playoffs really. The only certainty I have is that Joe Calzaghe was not only the best looking fighter, but also the best fighter of all time. Then it is James Toney.

Out of these three I would say Leonard as he could do a bit of everything and fought the best. Then it would be Mayweather as he can also do everything, but he picked and chose so he is below. Then it is Jones Jr as I have erased the Toney fight from my memory and he too picked and chose a little. In his prime he wouldn't get tagged much, but against a hypothetical Mayweather or Leonard he would get tagged and I'm not sure the chin holds up. Leonard and Mayweather have great chins.