Bollea may well have had a valid case against Gawker, but we'll never know. The idea that a case with a side funded by a vengeful billionaire could be fairly decided in our court system is absurd.
That money's not gonna conjure up evidence from the luminiferous aether.
Hogan is a famous, well-liked millionaire[0] already. And he almost certainly doesn't like Gawker.
So maybe he thought, "I can give up some of these millions and these parasites will not publish another damned lie again". In return, he also gets the eternal gratitude of people who hate Gawker (all decent human beings).
Seems like his actions align quite well with his interests.
Your own link says he is no longer a millionaire. He changed from financial motivations to moral superiority after the investment of someone who wants to destroy Gawker (not that Hogan might not also want that)... reducing your ability to receive damages doesn't seem to align to me as well as it does to you.
Me, I'd take that cut.
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.
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.
It was directly related his reason for disliking them. In fact, it was practically the same reason.
> and apparently influenced the process of that lawsuit with the aim of destroying Gawker to the detriment of Bollea
How so? Bollea was already a millionaire; he didn't need the money, and he wasn't materially damaged in any case. He wasn't going after Gawker for the payout; he wanted to see them punished for what they did to him, and dissuaded from doing it to anyone else. This outcome serves his interests much better than a bit of extra money would.
If Gawker goes bankrupt, it won't be because they're horrible people, it will be because they overstepped the bounds of the law.