Given the current state of confusion surrounding the President-elect’s policy platform, I think this Medium piece from August discussing the “why” behind Mr. Thiel’s RNC endorsement of Donald Trump is particularly salient. A brief excerpt:

Appearances aside, why of all people would the co-founder of PayPal and notorious libertarian be throwing his weight behind someone as controversial and volatile as Trump? Trump’s core two issues, trade and immigration, are not known to be big concerns for Thiel. If anything Thiel, like many in Silicon Valley, wants dramatically more skilled immigration. Thiel is from an immigrant family himself. He once even pledged funding for a scheme that proposed doing an end-run around immigration quotas by hosting foreign born tech founders on an anchored ship in the international waters off San Francisco. So much for law and order.

But before chalking it up to raw contrarianism, another one of Thiel’s infamous character traits, a closer look at his philosophical fixations and theory of entrepreneurship reveals a method to his madness. I admit that this is speculative. But in the tradition of Leo Strauss, Thiel sees value in layering meaning for different audiences — which opens him up for a more speculative interpretation.

Read the entire piece here.