Whatever Thiel's beliefs or motives, Gawker published a private sex tape for no legitimate reason. When a judge ruled they had to take it down, they disobeyed the injunction.
As Thiel points out, one social problem that this exposes is that even a single digit millionaire like Hulk Hogan didn't have access to the legal system. Hogan should have been able to get the result himself, but needed a billionaire to finance him.
They also created, hosted and pushed a "celebrity stalker map" for the express purposes of stalking people. There is a laundry list of reasons to have no sympathy for Gawker, and enough for many people to have wanted to see some comeuppance.
>We are not better off as a society when billionaires with histories of poor morality can arbitrarily destroy media companies.
We are better off when a company that goes too far, legally, faces ramifications for their actions. Even if the cause for those ramifications was less than pure; The motivations of the person who caused the action are kind of irrelevant to the action and result that occurred.
The worst part of this situation is not that Thiel funded someone else's lawsuit, but that access to justice required and requires that kind of funding. Not that Terry Bollea had his case handled without worry, but that everyone else does not.
Gawker was exceptionally stupid both in their reporting and in court, joking (so they say) that they would post a sex tape of a child as long as it was over the age of four. That doesn't play well with jurors. They had no respect for any concept of personal privacy. We are absolutely better off as a society without them, and without any other media companies that behave in a similar shitty manner.
Being a media company is not and should not be a shield from civil lawsuits or prosecution. Media companies should be in danger of being sued to death if they behave as badly as Gawker did.
"Oh no, a politician said behind closed doors he's going to nuke COUNTRY! We can't write about that, though, we'll get sued!"
Anything that restricts the first breaks democracy, your claim is Step One for any fascist uprising.