Can you point me to some examples where an individual financed litigation against a media outlet or journalist? I don't doubt they exist, but I can't think of any specifically.
When quite a few individuals took News International to court between 2009 and 2011 for illegally eavesdropping on their mobile phones in the UK, a number of them had their legal costs underwritten by Max Mosely. This is just the same thing: a wealthy individual making sure that legal costs do not preclude action against Gawker.
It's exactly the same thing. Mosely had his privacy violated by News International. Thiel had his violated by Gawker. Mosely set up a war chest to assist those taking legal action against News International. Thiel did so for those taking action against Gawker. Both had an axe to grind with news organisations they felt were behaving badly. Both assisted individuals with legal cases that would have otherwise gone nowhere because of the high cost of the legal system. Both News International and Gawker have relied on this in the past.