Thought experiment: who/what is the 2016 equivalent of circa-2013 Peter Thiel considering a candidate to endorse in the next election?
Consider that Trump was openly hostile toward Apple on the campaign trail, and that Tim Cook himself is gay, and the GOP establishment wants to roll back protections for LGBT+ individuals.
And consider Apple's vast war chest, which could really make a difference assuming Citizens United isn't overturned.
And I really don't think there's been a 180 on surveillance. I think the only people who were supporting the surveillance apparatus were the same people of an authoritarian bent who are now supporting Trump.
You are seeing ideological inconsistency where there is none in an effort to make your political opponents appear as hypocrites.
And the folks who voted and agitated for surveillance state champions Obama in '12 and Clinton in '16, of course.