I don't see the comparison between Trump and Obama (or Trump and Hillary). You may not like them, or you may like one of them, but their fields of experience and knowledge of elected office and government vary considerably.
Distinctions can be "
forced" to make artificial contrasts and/or they can be "
melded" into a generalized comparison. In this case, I have made a "
melded" generic comparison. Trump, whether you like it or not, has demonstrated business success. Theoretically, success as a business person could mean success as an elected person.
You have made an artificial distinction of "
elected office". Just because one is elected and has served in a particular elected and/or appointed government position does not mean that they actually have credible "
experience and knowledge". I would contend that neither Obama nor Clinton have demonstrated any competence in governess. Therefore, they meet the criteria of this thread in being highly paid clueless individuals. Trump (on the other hand) even if he is considered despicable and has not held an elected position, has demonstrated management competence that could carry over to the public sector.
PS: I am not a Trump supporter. I have been patiently waiting for Trump to
implode based on many of his rash statements. For a business person, many of his statements related to economic policies have been ludicrous. Unfortunately, his implosion has not yet happened, possibly as a populist reaction to the incompetence of Obama/Clinton.