I am ok with Thiel thinking Trump would win. What was a disappointment for me is that Thiel actually believes Trump was a good candidate and (I speculate) agrees with his platform. Also, apparently has no problem with the incendiary and hateful speech of Trump
He explains his rational argument here[1]. Basically his argument is "don't take Trump literally, take him seriously". 1. https://www.youtube.com/watch?v=ob-LJqPQEJ4
The problem with authoritarian governments is that they can delay plans but never forget about them.
If Thiel really think that, then he is not only an opportunist but also a fool.