Oooo. Isaac II Angelos... now there's one leader that's tough to beat.

This is gonna be a hard decision. For my own choice, I'm eliminating Stalin, Crassus, and Santa Anna on the simple grounds that they were all great and effective leaders -- though sadly flawed. Santa Anna in particular did extremely well against the lesser American forces that had faced him; I'd submit that it's no great shame to number among Winfield Scott's defeated foes.

Haig is tough to beat, though - massed infantry charges over pre-sighted ground at machine gun nests and rifle trenches without benefit of effective artillery support may seem wise the first time, but on the fiftieth attempt one might be expected to have learned better. It's his high position that elevates him beyond mere buffoonery; theater command grants him a truly epic fail.