Bollea's lawyers, as funded by Thiel, then decided to specifically drop the claim that would allow the damages payout to have been made from insurance. That's fairly vindictive.
Especially given Thiel's motive that "they outed me" - come on, Thiel's sexuality was probably the worst kept secret in the Valley. When you pose shirtless on a gay cruise, I think it's fairly safe the rest of the world didn't need Valleywag to tell them of your homosexuality.
I think a lot of what Gawker has done is repugnant.
But this is analogous to me making a bad mistake (even breaking the law) and causing a lot of damage in a car accident. In the civil trials that follow, I'm sued for damages, distress, medical bills, and the like. All well and good, as I should be.
And I have insurance. As I should have.
Except you don't like me, because I previously attacked you verbally.
So you say "Actually, your Honor, we're dropping all claims that are proximate to the accident itself, and only suing for everything that happened after the fact." which ever-so-conveniently takes my insurance off the hook for its ability to pay.
And you only do this -after- being assured you'll win, so no-one can question your real motivation (apparently, there was all this damage and distress you suffered, and you want recompense. Except now you don't, because you're removing the only realistic mechanism for you to obtain any recompense).
I don't think "secret motivations" and secret financiers should be a part of an open court system (and indeed, secretly financing lawsuits used to be and in most places is still illegal because it raises more ethical and moral questions than it answers).