Therefore, a deep pockets agent funding every potential lawsuit from other parties they can find (or stimulate), increasing the number of such suits and the likelihood that they will go to trial, can, simply by taking enough swings, eventually impose a combination of legal costs and judgements that will financially destroy the target; actual unlawful behavior may reduce the time it takes for this strategy to succeed, but isn't necessary for it to work.

So, given Theil's demonstrated proclivities in the multiple lawsuits he was funding against Gawker, I don't think the statement that Gawker would have been okay if they had stayed within the law is warranted.