It will not happen even if they were fighting in the same year because Jack won't fight Black like his refusal to fight Harry "The Black Panther " Wills. I am not sure who will win but one thing I am sure of is this won't go the distance since both can punch. The first scenario is Jack swarming a slow starting Joe Louis and TKO him. If Max Schmeling right cross can put Joe down then so can Jack. The second scenario is that Jack, a fast starter was ahead on the scorecard, get over anxious and run into Joe powerful combination like Billy Conn did....and got KO in the latter round.
The mauler and the boxer.
This could be a great fight, with either winning. Neither was undefeated and both have a great chance in this match.
I think Lewis is a better boxer and would probably win in a decision.
Louis' skills and scientific knowledge of the sport would propel him to victory against a crude swarming mauler like Dempsey.
dempdey