You're kinda pushing the envelope with the whole "celebrity" thing.
According to your logic, Kanye will win in 2020
obama ran on a nearly identical platform in 2008. His "change you can believe in" was this vague, anti-establishment, populist platform that really didn't stand for anything.
People want to be a part of something. They want to feel connected and trump lets them connect their tv watching familiarity with this big political movement. "I had trump's back from day one!" and other nonsense.. even if they have no clue about his political positions or plans.
Trumps' lines of "we will be winners" and 'we will be great" are very muddy and vague, and let everyone assign their own value to it... and people do exactly that.
Trump is a liberal that embraced the populist anti-obama movement. Repubs will regret him for a decade. He's not a conservative, he's not professional. He's an angry tv star and a brilliant marketer.