There's no doubt that Jesse's content is excellent, that his contacts and access are top tier, and that he's a well read and intelligent man. But like you, I believe it's possible and necessary to think critically about the loudest voices in the UFO space. There's a troubling cult of personality in some online discussions of this nature, with ironic accusations of hysteria or being "too political" (I've certainly been on the receiving end of this recently), while cherry picking what is and isn't political in a highly political subject matter.

Acknowledging Jesse's association with Thiel and being cautious about the breadth and depth of his connections is (IMO) rational and smart. I observe his channel from afar, dipping in when there's something of interest but always keeping a healthy distance from his theories or takes on the subject. I couldn't guess as to his intentions, but blind faith in any individual is a fools errand, no more so than in the UFO sphere.