The issue, as usual, should be with the system itself.
Is what happened here unjust? Is it wrong for Gawker to have had to pay the $140M? If you believe so, then your complaint should lie with the court. People should expect justice in court, rather than "typically" avoiding it via settlements and insurance. Our judicial system should be robust enough to make the motivations of a lawsuit's participants irrelevant. No matter how badly Thiel wants to destroy Gawker, they should only be liable for an appropriate amount of damages. If the court failed Gawker there, that's the court's fault.
On the flip side, if you believe the settlement was just, then it's Gawker's fault for doing something so bad that it cost them $140M in the first place.
EDIT: At least 6 downvotes now, but no replies. If you disagree, can you defend your reasoning at all?