It's because he's a caricature of what a President 'should' look like.
As if he'd been designed by a committee for a Ken Burns movie.
Ultimately the thing is a *LOT* of people are getting the same vibe from him, including conservatives.
From his own website:
.. No Republican candidate ever captured the nomination after having trailed so many rivals at one time or another in straw votes, fundraising, public opinion polls, and buzz. They came at him in waves, as though they were running a relay race and Romney was running a marathon by himself. In the ended, he bested the entire tag team of Trump, Bachmann, Perry, Cain, Gingrich & Santorum.
Left unsaid is that he didn't exactly 'beat' the others, he just waited around till they all dropped out.
The others, with few exceptions were all total wingnuts with serious mental problems. I think Santorum held on so long because he seemed to be openly advocating replacing the Presidency with a preachers pulpit.
None of the others can afford to keep on funding a bid for presidency without party backing. He can do it out of pocket change.
If he were to spend 10% of his net worth on this presidency he'd be spending: $23 million(ish)
On the subject of money, I find myself thinking that he actually has a lot more that's undeclared, or available.
I guess you could say he's the Gordon Geckko of politicians.
Rich bastard who honestly thinks its great darwinistic capitalism is the best way to run things. He can't connect with the majority of the country, because he's in a different timezone. The 1% time zone where making almost 60k per DAY for doing nothing, and occasionally supplementing it with some speech money for the pocket change of 300k. Money is meaningless to this guy.
No, this guy has no relation to the average person. Not even the average 'rich' person. Or, as Chris Rock would put it: there is rich, and then there is wealthy.