In my opinion, Trump will succeed not because of his political prowess, but because of who he resonates with.
People are tired of the elite ruling, making decisions based on cronyism and who lines their pockets. Trump isn't afraid to call them out.
The elite don't seem to understand that the non-elite vastly outnumber them, and are tired of their voices no being heard or making a difference.
Will Trump being president be a disaster, probably.. but at least it would shake things up and make the elite take notice how easily they can be replaced by the unsatisfied masses when the option presents itself.