[The problem] I mean is [modern] man’s inability to state his opponent’s view, and often his inability even to state his own.  . . . There is everywhere the habit of assuming certain things, in the sense of not even imagining the opposite things.  For instance, as history is taught, nearly everyone always assumes that it was the right side that won in all important past conflicts. . . . Say to him that we should now be better off if Charles Edward and the Jacobites had captured London instead of falling back from Derby, and he will laugh. . . . Yet nothing can be a more sober or solid fact that that, when the issue was still undecided, wise and thoughtful men were to be found on both sides.  . . . I could give many other examples of what I mean by this imaginative bondage.  It is to be found in the strange superstition of making sacred figures out of certain historical characters, who must not be moved from their symbolic attitudes. . . . To a simple rationalist, these prejudices are a little hard to understand.

From G.K. Chesterton’s “The Thing.”

Chesterton, as usual has a wonderful eye-opening point here.  But, as usual, after he blows you away you need to step back and make sure you agree.  The question is, what wars would have been better if the ‘other’ side had won?

Let’s remove the very obvious ones from contention.

Clearly the world might have been better off if, for example, the ‘Whites’ had won the Russian civil war against the ‘Reds.’  On the flip side, the right side won W.W. II.  I’m interested in the more controversial examples.

I do think the right side won W.W. I.

Some would disagree, but I say the right side won the American Civil War.

I say Europe was better off that Napoleon lost.

I realize that it is harder than we might realize to think of many wars that we wish would have gone the other way.

If we take Chesterton’s example, the Stuarts did not have a great track record, and it is hard from my perspective to see that they ‘should’ have won.  But I would love for someone to make a case for it.

Can anyone make a case that Carthage ‘should’ have won the Punic Wars?

Some might argue that the ‘wrong’ side won in the Peloponnesian War.  But in my opinion Athens had descended into self-worship and lost what made them great by that point.

I can offer a few moderately controversial assertions.

I would argue that the world would have been a better place if Phillip lost at Charonea, or if Alexander lost at Issus or Guagemela.

Greek democracy limped badly by Phillip’s time, and may never have returned to greatness.  But Philip snuffed it out completely.  By the time the Romans meet the Greeks, all the Greeks have to show them is absolutism, and this disease seeped into the Roman political consciousness.

Alexander obviously has many admirable qualities, but I don’t like him.  He was a butcher.  His success inspired others like Caesar to kill for glory.  His success romanticized him.  Maybe if he had lived he would have turned sour to those that came after him, but his early death sealed his reputation as the ‘boy conqueror.’  His failure to establish a workable political system led to the splintering and continued disintegration of the Greek world.  Though I would agree that Phillip & Alexander don’t create Greek weakness, they capitalize on it.

Can someone else make a good  and controversial case that another major conflict should have gone a different way?