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.