Gawker didn't lose this trial because they ran out of money to pay their lawyers, they lost because a jury of their peers found they were guilty as sin.

They lost because a billionaire, who didn't like them for reasons entirely independent of the merits of the case, spent time and resources canvassing for opportunities to punish Gawker.

As Thiel himself said, "even someone like Terry Bollea who is a millionaire and famous and a successful person didn’t quite have the resources to do this alone."

Thiel also said that, but for his involvement the plaintiffs would have accepted a pittance. The outcome is largely a consequence of an the intervention of an outside party, not merely the merits of the case itself.

Gawker is a company with $45 million in revenue. They have plenty of money to defend themselves from a single lawsuit. If anything, Thiel just leveled the playing field.

Well, in terms of resources, Thiel has more than Denton, who in turn has more than Bollea.

I think it's a moot point, since both Thiel and Denton have enough money that throwing more money at lawyers would do practically no good. Yes, people with more resources win more lawsuits, but there are diminishing returns.