Wait a minute. Gawker is no righteous hero here. Let's see if I understand correctly. Gawker outs Thiel (which is nobody's business, yet Gawker decided to make it people's business). Gawker at some point later posts an illegal SEX tape (again, nobody's business). Now, we're supposed to feel sorry for Gawker because Thiel wants to help out another person who was WRONGED by Gawker? Wow. Just wow.
I don't feel bad for Gawker at all. I do, however, feel concerned that a rich person like Thiel can buy litigation. That's a highly dangerous capability. He's using that power for good in this case, but I doubt he always will.
Welcome to the legal system. Money allows you to mount lawsuit (frivolous or not) and mount effective defenses against them.
The problem is when there's an imbalance: when a tech giant sues a small start-up (e.g., Zynga suing over the "Saga" trademark) or when an individual elects not to sue a large organization because the costs are too high.
Thiel (and Newegg re: patent trolls, and EFF, and ALCU, and others) are evening that money balance so justice can actually be served.
Can they use this power for evil instead? Of course: and it happens every day already. That's the point.
The anti-Thiel arguments come down to: "Even though Gawker was proven guilty in a court of law, it's not fair because Hogan never should have been able to mount the lawsuit in the first place." In other words, Gawker should have won because Hogan has less money. All Thiel did is even the playing field.
If this was about freedom of the press, they would have won the lawsuit. They didn't. End of story.