[Fastidious]

You are assuming the vast majority sees CNN, etc. and/or reads the NYT. That, I think, is too bold.

I don't think there is anything in common between the two, from personalities, party affiliation, to how they conduct themselves in public.

[toyg]

I'd say they have a common hatred for Ed Snowden and common positions on FBI-mandated iPhone unlocking, to start with. And the fact that they lived in the same circles for the last 20 years suggests they likely share much more than that.

Hillary was also born with money (albeit less than Trump) and was a Goldwater Republican before the antiwar tide became too big to fight.

(Party affiliation of political personalities in the US is a joke. See also: Joe Lieberman, another guy living in the same NY circles as Trump and Clinton. Don't take labels seriously, look at the policy, and you'll see the differences between Clinton and Trump are mostly cosmetic.)