One can argue that this was always the way of the world -- and it's only coming to light now, but I think that this is a far too cynical view IMO. It neglects the steady decline in political participation, party/union membership and actions a single individual can take.
Keep in mind, that this is not only a problem in the United States -- maybe its just more visible there. My home country Germany has more than enough shady connections between economic execs and the political machine.
Thiel has unusual politics that don't fit neatly along the right-left spectrum and lucked into a candidate that matched them more closely than anyone who had come before.
That's because it's more of a grid. You have 2 axis: Authoritarian/Libertarian, Economic Left/Economic Right.
If you're looking at it as a line, all sorts of things "don't fit neatly".
Whether this ends up being a shrewd move or a strategic blunder remains to be seen. I also thought that it was pretty smart in a realpolitik sense when he did it, but now I'm wondering if he's won the battle but lost the war. There's a lot of tacit power in the heads of various SV engineers, entrepreneurs, and executives, most of which is currently devoted toward making people click on ads, but which could be a force to be reckoned with if their ability to stay in SV and continue getting people to click on ads were ever directly threatened.
But maybe that's understandable, too. "The squad" has become the face of the Democratic Party, and the squad and Trump are neck-and-neck in a race to appeal to two-year-olds. Seems like both sides forgot that two-year-olds can't vote. If the Democrats had the appearance of competence and sanity, they should easily beat Trump, but at the moment, they look equally insane.
If the primary process produces someone who is not extremely left, someone who can look "presidential" rather than getting into a name-calling war with Trump, and someone that actually sounds like they care about the blue-collar voters, Trump should be gone.
Take Pelosi, for instance. It can't be Pelosi, nor someone like her. Pelosi seems to stand for Pelosi being the speaker. She doesn't seem to stand for any particular policies, other than "not Trump, but not something that's going to cost me the speaker job (even if by killing the Dems in the 2020 elections)". That doesn't win many votes in the Rust Belt.
[Even though I do not necessarily agree with you exactly, I tried to restore your comments visibility because of your long standing, seemingly in earnest, HN contributions.]
I had forgotten about her promise to relinquish.
If Trump had lost, Thiel would have taken a minor reputational hit based on Trump's pre-election behavior, but since no one thought he would win anyway, it could have been written off as him just taking a chance on an outside candidate. None of the really controversial stuff would have happened, so worst case scenario Thiel looks kind of foolish and wasted a bit of money.
If he had backed Clinton and she won, he would just be one of many Silicon Valley backers, with no particular voice over and above the other billionaires.
But now, Thiel is the only person in Silicon Valley who the President will listen to. That's got to be worth way more than the 1.5 million or whatever that he spent on it.