They were publicly sharing an intimate video of Hogan without his consent, he got a court order telling them to stop and they just refused to obey it, stating that they had a first amendment right to do it. Except, Gawker got the constitution wrong - and apparently didn't even ask a lawyer before refusing to obey the order -, which is why the later law against sharing intimate videos without consent is uncontroversial

Hogan was in the top 1% and even he couldn't afford justice when a large media organisation committed a blatant violation of his rights. His need for Thiel's support isn't an example of oppression of those organisations, it's an example of their power.

Yes. It was maddening seeing news orgs everywhere yawn at this process. It was an obvious proving ground event - and today is being more widely deployed.

- "Weinstein's attorney Charles Harder, who was then known for filing the suit that bankrupted Gawker, said his client would be suing The New York Times,[140] but by October 15, 2017, Harder was no longer working for Weinstein.[141]"

https://en.wikipedia.org/wiki/Harvey_Weinstein_sexual_abuse_...

There were multiple other news companies (not including the Times) that were successfully dissuaded from publishing anything about the Weinstein accusations, by his litigation threats.