How much damage has Peter Thiel done to free speech? This is what Peter Thiel will be remembered for.
I think you're asking a rhetorical question where the answer is in the affirmative. But I would actually like to know how much damage Peter Thiel has done to free speech. Gawker broke the law. It's great they got ended.
Why do so many people ignore this fact? Yes, Thiel funded a lawsuit that bankrupted them. But he won that lawsuit because Gawker committed a crime. I don't see how what Thiel did is any different than when an organization like the ACLU, NAACP, or EFF gets behind a court case that aligns with their political causes. Either we agree that a third party is allowed to fund a legal case for political reasons or not. Isn't that in and of itself an issue of free speech?