If we're talking tech, Germany would win no contest because theirs is what, 100 years more advanced? If we're comparing military conquests however, that would go straight to napoleon.
Napoleon was an actual general, and a pretty damn good one. The only crippling mistake he made was attacking Russia.
Riddler was a politician. He was able to rally the people to his cause, but was a loving buffoon when it came to directing the army.