I have to admit, I've always been conflicted about this. On the one hand, yes it is a dangerous precedent to let the rich destroy publications they don't like by funding any possible lawsuit against them.

But on the other hand, there seems to be an assumption that journalists and the media should be immune to punishment for when they do stuff that potentially destroys people lives, careers and reputation. Gawker didn't have the right to post this content and didn't care that the courts found against them.

And when you consider that millionaires and billionaires often own media outlets as well, that can be worrying as well. What about a Murdoch esque figure trying to push their own views on society (and discredit opponents) through their newspapers and publications?

What Thiel did here is potentially worrying, but so are the other possibilities from the media site.