A different way to look at it might be that in most cases, an illegal deed might be overlooked simply because someone didn't have the funds to see it through the court system. It's one thing if someone is funding endless lawsuits just to drive someone out of business, it's another for someone like Hogan to have a legitimate case, and for Thiel to fund his lawsuit. Thiel's funding of the case did not influence the judgement against Gawker, it simply allowed it to proceed further than if Hogan ran out of money.

I agree with what I think you're saying, that we should be careful about allowing someone to sue someone out of business simply out of spite; however, I think there's something to be said for someone with deeper pockets funding a legitimate suit. It might be comparable to things that the EFF funds, or that the ACLU takes on -- they have deeper pockets, and can take the financial hit that someone with a legitimate claim may not be able to take.

Imagine if Gawker published the same thing of some average middle-class person. They can't afford a high-priced lawyer, so likely Gawker gets away with something that, if it went to court, they would lose. In this case, the bully ran into someone who actually could fight back. As far as I know, Thiel didn't fund endless lawsuits just hoping to run them out of money. He funded a legitimate lawsuit that ended up with Gawker being found in the wrong for.