A general point: I fear Adams attributes positions and beliefs and intentions to Trump which, from Trump's actions and public statements, are not justifiably attributable to Trump.
Adams predicting that Trump would win at a time when nearly everyone else thought Trump was a joke candidate is evidence that Adams has special insight into Trump. And this wasn't a mere prediction. Adams essentially bet his entire reputation on this claim. Adams often makes falsifiable predictions such as when he said that Obamacare would essentially never be repealed and that Snapchat had a dim future.
Recently, James_Miller posted a conversation between Sam Harris and Scott Adams about Donald Trump. James_Miller titled it "a model rationalist disagreement". While I agree that the tone in which the conversation was conducted was helpful, I think Scott Adams is a top practitioner of the Dark Arts. Indeed, he often prides himself on his persuasion ability. To me, he is very far from a model for a rationalist, and he is the kind of figure we rationalists should know how to fight against.
Here are some techniques that Adams uses:
Overall, I think what Adams is doing is wrong. He is an ethical and epistemological relativist: he does not seem to believe in truth or in morality. At the very least, he does not care about what is true and false and what is right and wrong. He exploits his relativism to push his agenda, which is blindingly clear: support Trump.
(Note: I wanted to work on this essay more carefully, and find out all the different ways in which Adams subverts the truth and sound reasoning. I also wanted to cite more clearly the problematic passages from the conversations. But I don't have the time. So I relied on memory and highlighted the Dark Arts moves that struck me immediately. So please, contribute in the comments with your own observations about the Dark Arts involved here.)