Even though I'm a Kinsey Zero, as a privacy advocate, I'm very happy that powerful, good people of a historically-beleaguered orientation (Tim Cook, etc.) have become forces to be reckoned with on the privacy front.
Forcefully outing people is not news, it is harm.
I'm not sure what that has to do with it.
That struck many legal observers as odd, given that most lawyers seeking large payouts want to include claims that are insured against because doing so increases the chances of a settlement.
Lawyers seek large payouts? Isn't it the plaintiff that calls the shots? Hulk Hogan is already a millionaire (but not to the degree of the payout in this case), so it may not just be Peter Thiel that wanted Gawker to hurt. Some fairly damaging stuff about Hogan has surfaced because of the trial, which, surprise, was covered by Gawker[1] (and without a disclosure regarding the lawsuit until a later update).
1: http://gawker.com/hulk-hogan-refers-to-fucking-niggers-in-le...
In the end, I don't think it really matters. If you did stuff your insurance doesn't cover and get sued for it, that's your fault. You don't get to decide how the other side responds. If your business model relies on this behavior, you should really be keeping this in mind. (These are generalizations. I'm not sure what Gawker is guilty of, if anything, and what their business model really consists of).
It's one thing to express discomfort that someone if funding a frivolous lawsuit, but without some opinion on the merit of the case, I'm not sure how the involvement of money should be seen as a good thing or a bad thing.