I really don't understand what everyone thinks is so evil what Thiel did. Did he have a personal reason to hate them? Sure. But the fact is that Gawker lost in the court of law. If you think this is wrong, argue about the case or the law. Where the money came from or if Thiel pushed Hogan to go for more is irrelevant. The judge and the court agreed.
There is a balance on the free press that needs to remain or there will be times where truly libelous stories will be published with no recourse. I am no advocate for making it easier to sue like Thiel/Trump want, but I can't take this as an attack on free press. If Thiel has tried a bunch of times and lost, or if I thought that Hogan had no case then I would probably agree with you.
Do you understand how the rich take advantage of the law and of courts? Biases by judges? The film goes into all that but the fact is that the rich can wield and twist the courts if they're smart, and that's what Thiel did through several avenues.
It's dozens of little things that add up.