I understand how he won. As SD said, I don't think this was about Obama v Drumpf. I do think it was largely about "putting the whole system on trial." A combination of Hillary being very much a part of the system along with her being a shitty candidate in general was enough.
I still struggle with how a majority of Drumpf supporters agree that he is lying but somehow trust him. There are probably rare instances, but I don't think Obama or Bush blatantly lied to the public. They largely intended to do pretty much everything they said they did. Drumpf is not going to try to build a wall. He is not going to appoint a special investigator to lock Hillary up. He is not going to ban Muslim immigrants. I don't know any reasonable person that thinks he will even try to do these things. But there are reasonable people that trust him to carry out other campaign promises. That disconnect is strange to me.
This is pretty much where I'm at. I totally get a lot of people's sense, both real and imaginary of disenfranchisement (it's a common bond for example with Bernie supporters, people unable to advance or shut out in basically economic purgatory),
I get people hating a lot of corruption, back room dealing thing (though I really just assume that anyone in position of power, regardless or country, or type of position, be it president, chancellor, senator, dictator, CEO, is doing that anyways, it's "just the way it's done" and while I don't like it, I just also assume that from that high of a vista some sort of greasing the wheels is needed to get things done)
So I get the anger, and wanting to upset the apple cart, take a chance and change things up, but it's just that. Him? Trump? The guy who's proven time and again to only enrich himself and burn everything else down, and has done that well before any of this presidential run nonsense. How you can trust him but he lies about a lot of things, and be ok about that, but Hillary has done several not great things either, but even if she happens to speak a truth, it can't be, she's not allowed any sort of a benefit of a doubt. Granted, she was a very poor candidate, so I'm not here to overly defend her, but it does speak to ChiCat's disconnect. I feel/think/see a lot of this disconnect as well.
I guess the thing I personally underestimated was a large populations hatred of the "establishment." I guess it's good to recognized how mumped everyone has been getting by the elites, I just find it funny the pick the "born into" prototypical version of it, rather than the self made version of it.