A large part of Trumps message was that Hillary was unsuitable as president. If Trump hadn't manage to get that message through and elevated that issue in favor of other issues much fewer people would have voted for him.
> This is why I agreed with Sama and not removing Thiel from YC. We have to listen to the other side and empathize so we can understand. Without that we all lose.
I think the point of opposing Thiel at YC have been lost on HN. It wasn't mainly about politics or opinions. Trump is less to the right than many other candidates and the politically viable opinions of Thiel isn't particularly controversial either. It was about the downside of the "bet" on Trump.
At the RNC Trump had roughly a 40% chance of winning the election according to 538. Thiel spent a couple of million usd and some of his time to have a 40% chance of being "friends" with the most powerful person in the world. That's a huge upside with almost no downside, especially if Trump lost, and therefor an easy bet to make.
If there were more downside Thiel would have had a harder time to make this bet and would have had to be more certain on his decision. Favoring more long term behavior in the political process. Instead just ran one of the cheapest political campaigns you can imagine.
All in all this together with other similar "investment" makes a fairly bad precedent for silicon valley in mixing politics and money.
With the risk of sounding "smug", I think most of this thread offers a poor analysis of the election.
The reason Trump won is, presumably, to a large extent that he managed to make his message more relevant. If this election would have been about schools, even in the same context, he most likely wouldn't have won and the deplorables comment wouldn't have mattered or even happened in the first place.
We've seen this in Europe repeatedly with new candidates offering easy solutions and a straight forward message, leaving the established parties on their heels trying to defend themselves. In Europe this normally results in 5-15% of the seats in parliament, while in the US (once you're in the running) this can win you the election because of the political system.