Actually, the chilling effect is due to that the lawsuit against Gawker only went as far as it did because Hogan teamed up with Peter Thiel, who had a personal vendetta against them over a story they had written about him. By all accounts, the issue was going nowhere until he got involved and funded Hogan. Thiel has now turned his attention on other outlets, currently attacking Techdirt for the (true) stories they wrote about Shiva Ayyaduria (who Thiel was also helping in a lawsuit against Gawker, among numerous other suits he was financing). That's the important part here - lots of lawsuits, some much more frivolous than others - were being launched because a billionaire doesn't like the outlet. If the Hogan case didn't bury them, he had plenty more lined up until something did.

What's being exposed is a situation where pissing off the wrong guy can bury companies in court (and legal fees even if they're found innocent), and that it's too easy for one rich guy with a vendetta to do this. The issue is muddied because Gawker were clearly in the wrong, both legally and morally, with the Hogan tape. But, this will still have a chilling effect on people writing factually and morally correct articles if they fear they'll piss off the wrong guy. That's the issue - Thiel is going around trying to shut down media outlets he doesn't like, the fact that Gawker were a horrible outlet to begin with doesn't negate that.

"There is a monumental difference between that and writing a negative article."

Yes, and his current target wrote negative articles about his current client, articles that are backed by solid evidence that they are true. Nothing Techdirt has said is demonstrably false, and their attacks on Shiva's claims are always backed by verifiable evidence. The Techdirt case is far more defensible than the Gawker one, but the same principles apply, as does the chilling effect it will be having on other outlets.