Thiel chose an easy target, and opened the door to destroying journalism.

As un-American as it gets but hey, he’s the right color with legal bundles of cash; so much for our cherished, upper to middle-class institutions.

Gawker was a garbage-tier publication. But I absolutely do hold that particular lawsuit against him:

Gawker didn't "out" Thiel in any meaningful sense. Yes, they published and it was tacky. But let's be very real: Thiel's social media and profile pictures were full of things like him shirtless on gay cruises and parties at gay nightclubs. The only people who learned Thiel was gay from Gawker were people who had no particular interest in him.

I also have significant issues with his bankrolling of Hogan's lawsuit against Gawker as an abomination of the legal system, including the right to face one's "accuser":

- Prior to Thiel's involvement, Hogan had already agreed in principle to a part ownership stake and profits of Gawker. He'd also already settled, and forgiven, the person who gave Gawker the sex tape in the first place.

- Lawyers paid for by Thiel pushed for him to drop that and push instead for bankrupting Gawker through damages (which were laughable, see below). (Hypothetical question, if you're an attorney, ostensibly representing Hogan, but you know the person paying your bills, Thiel, wants a different outcome for the case, when push comes to shove, whose interests are you going to represent? See the following point too).

- When the case and awarded damages -did- actually threaten to bankrupt Gawker, Thiel/Hogan's lawyers did the most illogical thing possible, if they were looking to recoup any money for their ostensible client... they dropped the one claim against Gawker that would have allowed their liability insurance to at least partially pay out. Remember, Hogan could use that money far, far more than Thiel.

(Re damages: The amount that Hogan had originally asked for seemed reasonable. Then after Thiel's lawyers got involved, the amount asked for was multiplied five thousand times.)

This included economic damages of fifty million dollars. For a man who had made something in the order of $20-25M his entire career? Who had a net worth at its peak of $30M, and at the time of the lawsuit, a NW of $8M? I highly doubt that TV stations pulling reruns of old WWF events, hair loss commercials and other endorsements was worth that. (They separately asked for emotional damages, too, to be clear. But there was near zero justification for this economic damages claim.)

I wonder how much Thiel paid Hogan under the table for this proxy lawsuit? Because it sure looks like he was playing puppeteer, and while Hogan had every right to be bitter about what Gawker did, his every action to resolve or plan to resolve the matter pivoted 180 degrees the moment "his" lawyers got involved, and perhaps unsurprisingly, the outcome perfectly aligned with Thiel's goals.

If you mean in terms of political party leaning, we've had many years to observe how Rich vs Poor can override Right vs Left.

He has been politically active trying to roll back CDA Section 230 protections for social media companies because he conflates social media algorithms being “editorial” with what actions are actually protected by CDA 230.

He made an pinned Instagram post about his association with this group (link to his account, not to the post):

https://www.instagram.com/hitrecordjoe/

He’s involved in the effective altruism movement and Hollywood AI policy