> As a result of the size of the legal team's war chest

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...