I'm not a Trump supporter. Nor am I a Clinton supporter. But I'm not really puzzled about why Trump won. Here's an explanation from Mark Steyn:
The establishment of both parties spent the last year telling his supporters they no longer mattered - they're too old, too white, too male, too bluecollar, too rust-belt, too too tootsie, g'bye; they're old and fading and they'll be dead soon. This is, in fact, an over-broad generalization: Trump pulled more millennials than Romney, and more of the Latino vote, and he doubled Mitt's share of the black vote.
Even so, it was too much to expect this New America to wait for this old, irrelevant America actually to kick the bucket: they had to hasten 'em into the grave by endless taunting that everyone matters more than you. So that, in nothing flat, transgendered rights suddenly become a huge urgent public-policy priority requiring instant federal bathroom ordinances and congratulatory calls from the White House to Caitlyn Jenner. And you've never met a transgendered person or know anyone who's met one - and yet they matter, and you and millions like you don't. And both the left's social-justice warriors and the right's psephologists are insisting that you'll matter even less next time.