Probably a lot of it is that Trump is so openly boastful and egotistical that even things that might normally be dismissed as gaffes or missteps from other political figures are magnified by his enormously self-inflated sense of self. If he billed himself as he is, it wouldn’t be quite so profoundly obvious, but he always has to claim he knows more than X about anyone else. That he has the best Y of anyone.

Et cetera, et cetera, et cetera.

From a distinctly nonpolitical perspective, there’s really nothing good to say for a person who acts like this. Even if it’d be true. Even if you agree with his actions. Praising someone with an ego that huge is only consequential.