For me, one clip kind of summarizes this:
https://www.youtube.com/watch?v=_ul2OuvPOQE
Trump, to me, is the inevitable byproduct of a system where character arguments and labels are used to win what should be political, idea driven discussion. Just because you might disagree with someone else's vision for where the city/state/country needs to go doesn't automatically make them immoral. Words matter, and applying them to people you disagree with solely because you disagree with them means that those words matter less.
It becomes more understandable if you approach it from the perspective of 'if they're going to label X candidate for Y party with these horrible, nasty labels because they are running against Z party, then the thing we need most is someone capable of punching back against those labels and the people trying to apply them'. Whatever you might say of Trump, at this point he's a mud monster. No amount of mud people throw will stick to him (even when it should).
Two things can be true at once, and the other part is that it's difficult to say that morals matter to you and then be OK with what Trump does.
What I really hope comes out of all this is wider applications of the following two scenarios:
1) There is one standard (phrased in terms of yes/no questions with little wiggle room), and we hold everyone to it.
2) We stop demonizing people we disagree with. Before we apply a label, take a breath, and a few minutes, and try to set our disagreement with said person aside. Then, if the label applies, then apply it.