Large part of this comes from the fact that superheros rely on their special power whilst super-villains have to make do with more conventional means (intelligence), so this is largely fictional evidence.

In the real world I would not bet on Hitler/Stalin/Mao against Churchill, given the same resources. But to your point part of Churchill's power was understanding people (at least certain kind of people) - he called Hitler's end-game very early and against the prevailing political opinion at the time.