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Re:Peter Thiel to Donate $1.25M in Support of Donald Trump by untog on Sunday October 16, 2016 @04:57AM (#12717708)
None of what you wrote answers "why Trump?", though. If Thiel thinks he can somehow control Trump and get him to pursue a Libertarian agenda (which Trump's platform bares no resemblance to) then he's an idiot.

If he wants Libertarianism he should donate to Gary Johnson. Anything else is just opportunism.

Re:Peter Thiel to Donate $1.25M in Support of Donald Trump by maxerickson on Sunday October 16, 2016 @08:32AM (#12718311)
Flattering Gary Johnson isn't going to accomplish any political goals.

Getting him into the 3rd debate might moderately raise awareness of the party, but he isn't going to win the election. Full stop.

Re:Peter Thiel to Donate $1.25M in Support of Donald Trump by untog on Sunday October 16, 2016 @10:29AM (#12718737)
Neither, at this point, is Trump. So it's a bad investment either way.
Re:Peter Thiel to Donate $1.25M in Support of Donald Trump by harryf on Sunday October 16, 2016 @12:05PM (#12719225)
> Anything else is just opportunism.

But that might be it. Trump clearly lacks a well oiled political machine behind him like Clinton. Should he win power there will no doubt a lot of opportunities opening up for anyone with a cheque and an agenda. I guess 1.5 million is not much to gamble for Thiel and will pay back 1000 to 1 if Trump were to succeed.