Good read on the relationship between these two-
Rudy is slimy and desperate, but not stupid in the classic sense - all jokes aside, running NYC isn't easy.
Trump could be considered cunning in the same way that damn raccoon always manages to get the lid off my trashcan and make off with a weeks worth of moldy leftovers. Somehow he managed to get enough people to confuse the illusion of relatability with competence and get elected once during a once in a lifetime political alignment of planets - no way he's the mastermind of anything...