I would say Louis most likely by decision, possibly by knockout. If it turned into a war, which knowing Holyfields gutsy demeanor & willingness to trade, it probably would then I would say Holyfield would be out gunned and probably knocked out or stopped.
Holyfield's excellent combination of styles would be too much for Louis. Louis would be floored twice before gettin knocked out in round 8. Holyfield would get a point deduction for headbuttin in round one. Louis would try to land his jab but Holyfield slips/blocks it well and lands his right straight on Louis' paper-chin.
Holyfield was in an entirely different class than Louis. He faced too many heavyweights who were bigger stronger and faster than the men Louis defeated ( with the exception of B. Baer and P. Carnera. ) Holyfield wouldn't have a problem surviving Louis's onsloughts and would offer plenty of offensive troubles for Joe in return. Holyfield by wide decision or late stoppage.
Evander would be a very tough opponent for Louis, but I don't think he has the tools to beat Joe. Speedsters made Louis look somewhat ordinary, but Evander did not possess remarkable foot speed or have the in-built survival mechanisms of a Conn or Farr. Holyfield was also not a swarming type of fighter like Galento or Maricano (a style Louis admits bothered him) so there's nothing in Holyfield's style that is going to be particularly problematic for Louis. Holyfield was a very good counter puncher and he'd get his licks in, but he would not beat Louis to the punch. In most situations, Louis would land first and Evander would try to counter. Holyfield punches in bunches but in Louis he'd meet a man who does the same thing, only better and with harder punches. Holyfield does not (imo) possess the kind of power to pose a serious threat to Joe's chin. I like Louis by decision, because Evander was iron-chinned with a warrior's heart, but to my mind the better and more complete fighter was Louis.
I think you are grossly underestimating Joe Louis. Louis had great KO power in both hands, hands that were very fast. When moving around the ring he seemed like a plodding type of mover, but he would snap out ferociuos yet economically sound punches with great reflex speed. Evander would try to rumble and get tagged frequently. People underestimate Louis's intelligence, he would pick his shots carefully, short powerfull punches thrown in great cominbinations. The greatest fighter Holyfield has faced at heavyweight was Riddick Bowe (the 1st time), Louis is considerably greater than Bowe. Once Louis had Holyfield hurt, he would go in for the kill, the man was a cold assassin in the ring, he knew how to finish a fighter when hurt. Holyfied wouldn't look like a warrior at the end of the fight, just another victim, albeit a very brave one.
i think holyfield makes easy work of louis .ko3.im sure im gonna get a bunch of what the hell r u thinking,but like magoo said holyfield fought a different crop of fighters.there needs to be some sort boxing time machine one of us can invent and settle all of our then vs now matchups.louis was indeed salty but evander holyfield in his prime was one of the if not the best boxer ive seen.a total tactician,with ko power.a perfect picture example of a BOXER.
To me, Hollyfield is an ATG fighter, and an ATG heavyweight, a warrior who would give anyone a hard, hard nights work. But if you're picking Evander to beat Louis "easily" or without a problem, your pick really can't be taken that seriously, I think.