So sure he has a point, but he is also the one from whom I long ago learned that 'the perfect is the enemy of the good.'
George fathoms himself perfect, from which he is far, and picks at and demeans anything that doesn't fit his far from perfect picture, which is his own unconsciously fabricated picture of himself - a manifestation of his ego - gross pride. Thinking so highly of his ideas, and believing anything athwart thereof to be reprehensible, he's become himself the enemy of the good.
By becoming so, he's long been simply the bad itself.
Excellent points and good insights on what makes George Will tick. George doesn't have any fixed idealogy and is always just looking for an angle to convey his schtick. If Trump had some polish George Will would love him. Will can't get past Trump's style and is stuck on stupid. George would do better to stick to baseball. The world is passing him by.
I read a very early piece from the seventies, which I found in the American Spectator archives, in which George, though just as windy as he is now (I believe he learned sentence structure from the Apostle Paul), was actually rather humorous, the which, believe it or not, was his intent. Perhaps if he could exhume his funny bone, he might recognise how petty and mean-spirited he has become, and stop taking himself quite so seriously.
I could not phrase any better what is at the heart of Will’s problem than you did. Indeed, the perfect is the enemy of the good, as General George Patton liked to say about battle plans crafted by very timid souls.