Hi D&O,
Trump makes total sense when you understand Trump is a brand.
Trump doesn't create businesses. He brands them. Trump doesn't own the Trump Towers. He brands them. Trump doesn't own his television shows. He brands them. Who runs Miss Universe? He doesn't. He's the smile.
Joining the Presidential contest is a means to drive his brand upmarket. Now Trump is a Presidential brand.
Unfortunately, he screwed up and harmed the Trump brand because he has the skills of a brand promoter and not of a politician.
He's got the same gig as Richard Branson at Virgin. Except Branson knows how to avoid trouble better.