Then I came across something that might explain it all, including Obama's delusions of adequacy. It's called the Dunning-Kruger Effect.
The Dunning–Kruger effect is a cognitive bias in which unskilled individuals suffer from illusory superiority, mistakenly rating their ability much higher than average. This bias is attributed to a metacognitive inability of the unskilled to recognize their mistakes.Obama and many of his supporters most likely suffer from this effect, automatically assuming they have superior knowledge and skills to those surrounding them when in actuality they are less capable and competent than others. Conversely we operate under the assumption they have an undertsanding similar to ours when in fact they don't.
Actual competence may weaken self-confidence, as competent individuals may falsely assume that others have an equivalent understanding. David Dunning and Justin Kruger of Cornell University conclude, "the miscalibration of the incompetent stems from an error about the self, whereas the miscalibration of the highly competent stems from an error about others".
That explains a lot.