Earlier quoted context omitted.
Not OP, but part of it is probably his (successful) attempt to shut down a journalism outlet that he had a personal beef with by bankrupting them with proxy lawsuits. Free press, no matter how much you may not like the stuff an outlet chooses to focus on, is an important part of free democracy, and when billionaires can essentially just lay siege over non-legal matters I consider it an active attempt to erode modern…
You're conveniently ignoring the part where Gawker was doing illegal things and therefore lost the lawsuit (getting a verbal smackdown from a judge in the process). Your argument only works if the lawsuits were baseless and/or frivolous. I'm not sure how you can throw shade on Thiel -- would it be any better if media companies could freely ignore the law as long as the affected individuals lack the funds to take them…
The issue is that Thiel had no direct connection to that incident. The issue is that he funded everything because they outed him as gay (completely legal), with the express goal of bankrupting them via lawsuit. He didn't want them to learn a lesson, he wanted to fucking end them.
While he didn't do anything illegal, I think it absolutely counts as eroding modern society.