They don't have to win. It suffices to overwhelm the legal resources of their opponent.

That's not what happened though, they (Hogan) did win. Gawker was in the wrong. We're not talking about individuals, we're talking about global media brands. They can overwhelm most people with their resources, sadly only the rich can defend themselves.

But when the press defend themselves, it is obvious where the financing is coming from. Thiel's innovation was the secrecy of his passing ten million dollars to a third-party litigant.

http://fortune.com/2016/05/25/thiel-gawker/

I see no issue with that. We shouldn’t audit people before we give them a chance at justice. I’d gladly take his help if a large media company slandered me. I’d feel no obligation to disclose the source of my funds. I wouldn’t expect anyone to divulge that information.

And in fact, Thiel has stated that Gawker is not the only time he's doing this. I wonder if we'll ever hear about the next enemy Thiel's finances destroy.