That's not good, no matter if you happen to agree politically with said guy with too much money at this particular point in time.
What is frightening about Thiel’s involvement case is the playbook: destroy media companies that have been critical or embarrassed you, by secretly funding any and all lawsuits against them, even if frivolous.
Maybe. Thiel funded the destruction of Gawker for their crime against Hogan. He probably wouldn't've funded it if he hadn't had a personal grudge against Gawker, sure, but Hogan's lawsuit was entirely legitimate. If there hadn't been a legitimate lawsuit against Gawker, only illegitimate ones, would Thiel have funded those? We really can't say.
Did he actually do this? (all and any, even if frivolous)
Essentially, the bigger issue here is that Gawker could hide behind a bunch of lawyers even when they knew they were doing something despicable. Take that away, and things get fairer pretty quickly.
This is not the current standard. You can yell fire in a crowded theater all you want (probably). We no longer use the "clear and present danger" standard, instead Brandenburg v. Ohio changed it to be "imminent lawless action"[1].
1: https://en.wikipedia.org/wiki/Brandenburg_v._Ohio#the-decisi...
I hate that this example is always used. Yelling fire in a theator for a laugh isn't "expressing ideas". It's a kind of social fraud: in some sense we depend on each other to make society work and someone shouting that our lives are in danger when they are not is violating this trust. Not by expressing some philosophical ideal but by exclaiming something they know to be false.
There's nothing about the constitutional idea of free speech that says it has to be of philosophical value or true.
Just googled this. Thanks for bringing it up, I hadn't heard about this case before.