I am conflicted about this, and see merits on both sides of the argument on Thiel's actions. So I tried to draw an analogy: Let's say that there is some patent troll that only extorts money from small startups, who don't have the resources to fight back. Some billionaire of today, who in his past career was harassed by this patent troll, decides (both for revenge and for the greater good in his opinion) that the pate…
2) You can always use analogies from other industries, but you can also make a case that in the United States the press is something of a special case. It's the only private industry specifically given constitutional protection in the Bill of Rights. It's certainly worth asking--and potentially litigating--whether Gawker violated both Thiel's and Hogan's right to privacy, but we give the press more latitude than we do other industries for a reason.
3) In the example as you outlined it, where a "patent troll only extorts money from small startups," I wouldn't feel the same despite disagreeing with Thiel's actions in this case.
The difference, beyond what I've suggested above in (1) and (2), is one of precedence. People are focusing, understandably, on the specifics of this particular case. But we don't know wat other cases Thiel is funding against Gawker; we don't know what the merits are. And that's the whole thing: a billionaire unhappy with the way a media outlet has covered him doesn't need to find winnable libel and defamation suits against that outlet; he just needs to find ones good enough to get to trial and cost tens of millions of dollars to defend. If Thiel funded a half-dozen losing cases against Gawker, he might still bankrupt them.
And, again: precedent. What if instead of Peter Thiel this was Donald Trump? Hillary Clinton? George Soros? David Koch? What if the ultimate reason for the vendetta was because they brought out embarrassing secrets that were in the public interest?
While I understand why everyone is focusing on the "Gawker? Couldn't happen to a more deserving company, ha ha ha" aspect of all this, free speech cases don't always revolve around noble defenders with noble goals. As wary as I am of slippery slope arguments (use one once and you'll use them everywhere), "hey, this couldn't possibly happen to someone who's less of a jerk than Nick Denton" seems uncomfortably close to magic thinking.