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Very mixed feelings on this.
So? What's wrong with that?

Gawker is predatory in terms of how they approach "news". I'm glad they got hit back in kind (someone with resources took on their legal resources). I'm not sure they have enough redeeming qualities to overcome their bottomfeeding approach.

It just feels shady, an "anonymous benefactor" who's actually funding a legal assault he'd otherwise have no involvement in simply because he has an axe to grind. I agree with your feelings re: Gawker Media though- they're basically on par with Buzzfeed in my mind.
Buzzfeed has a lot of excellent reporting and long form articles.

I'm surprised that they're shamed on HN of all places, when they've found a great business model where they take money from clickbait to finance good journalism.

The "tak[ing] money from clickbait" is precisely the problem. Reputation matters.
But this "anonymous" benefactor happens more often than we think. Lots of times its someone indigent who gets a pro-bono lawyer or gets backing from interested parties to establish precedent --or to prevent precedent. I think the only newsworthiness in this comes from the "billionaire" adjective.
Gawker is crap, but it's awful seeing vengeful billionaires throwing money to suppress journalists.
In this case, the "journalists" posted a sex tape recorded without the consent of the person, and with no journalistic value other than to smear the person involved.
So Peter's basically choke-slamming Gawker because they outed him as gay earlier on. I'm conflicted because I think Gawker is a click-bait cesspool, but at the same time feel uncomfortable with someone else's desire for vengeance fueling a legal offensive.
How does the fuel matter? The case has legal merit or it doesn't. If you are assessing worth based on who is funding it, then you are looking at it the wrong way.
There is an exception to that where the playing field is so uneven that a small entity would be bankrupted just by trying to get to a legal result in their favour. I don't mean to suggest that applies here, though.
That's a very naive and optimistic assessment of how our adversarial legal system works. The $$$ you bring to bear on a case matters just as much as the legal merit. Poor folks are put in jail because their overworked public defender was sleeping when they should have objected. A billion dollar company can bury a mom and pop shop with patent litigation, etc.
I'm not sure what this has to do with what I said. The original commenter expressed that they "feel uncomfortable with someone else's desire for vengeance fueling a legal offensive." If the legal offensive has merit, why does it matter who is behind it?

It's one thing to express discomfort that someone if funding a frivolous lawsuit, but without some opinion on the merit of the case, I'm not sure how the involvement of money should be seen as a good thing or a bad thing.

I don't have any issue with vengeance fueling a legal offensive. I also think that Gawker crossed a very real line when they outed him in 2007. What concerns me is one billionaire can bring down and effectively silence a media outlet quietly from behind the scenes.
I'm not sure I would consider this him taking them down. The case has nothing to do with him beyond his money, and without the case his money wouldn't be doing anything here, so it's the case that's doing the work. He's just supporting it.
As a result of the size of the legal team's war chest they've removed language that would allow Gawker's insurers to pay any damages. This will hold Gawker liable and Gawker probably can't afford to bleed $140M without going under.
> As a result of the size of the legal team's war chest

I'm not sure what that has to do with it.

That struck many legal observers as odd, given that most lawyers seeking large payouts want to include claims that are insured against because doing so increases the chances of a settlement.

Lawyers seek large payouts? Isn't it the plaintiff that calls the shots? Hulk Hogan is already a millionaire (but not to the degree of the payout in this case), so it may not just be Peter Thiel that wanted Gawker to hurt. Some fairly damaging stuff about Hogan has surfaced because of the trial, which, surprise, was covered by Gawker[1] (and without a disclosure regarding the lawsuit until a later update).

1: http://gawker.com/hulk-hogan-refers-to-fucking-niggers-in-le...

If Gawker could settle and have their insurance company take the hit then Gawker itself would remain relatively unscathed. By preventing the insurance company from paying out, Hogan/Thiel have made it more difficult to win their case and more difficult to collect to monetary award. Also - by not settling Hogan's legal bills increase as the battle rages on. Gawker can outspend Hogan, but Gawker can't outspend Thiel.
Can Gawker outspend Hogan? He's reported to have $25 million. If Gawker can't take a hit of $140 million and survive, how much can they afford?

In the end, I don't think it really matters. If you did stuff your insurance doesn't cover and get sued for it, that's your fault. You don't get to decide how the other side responds. If your business model relies on this behavior, you should really be keeping this in mind. (These are generalizations. I'm not sure what Gawker is guilty of, if anything, and what their business model really consists of).

He's doing what most people would do if they had money to burn. Not saying it's good, but I think that's true. How many times have you heard "I'll f*cking sue you!" as an impotent threat? I like to half-jokingly say that my definition of wealthy is when someone can refer to "my attorney" and not be bluffing.
You might be more understanding if you had a preference that was still somewhat taboo (yet ultimately harmless) and expected the simple human courtesy of being able to announce it on your own terms.

Even though I'm a Kinsey Zero, as a privacy advocate, I'm very happy that powerful, good people of a historically-beleaguered orientation (Tim Cook, etc.) have become forces to be reckoned with on the privacy front.

Forcefully outing people is not news, it is harm.

It's only really concerning if you're looking to apply very broad principles to it. If you look at the full circumstances (what Gawker do, what they did to Peter, what they did to Hulk) then I think it becomes a bit easier to swallow.
Somewhat OT, but while I am not a reader of Gawker at all, I do enjoy posts on Jalopnic and Gizmodo quite a bit. It would be a shame if those sites got dragged down with Gawker.
I dropped this on another comment thread but think it'll apply here on the NYT take as well: My perspective is this won't have a chilling effect on real journalism.

This, to me, simply re-iterates the ingrained expectations of conduct that journalism attempts to envelop and embrace as a profession. There are newsworthy stories, and there is muck raking. They are different, and on completely different ends of the integrity scale. Personally I like that the courts are a venue for recourse when there is perceived harm; sure, things could be improved mechanics wise but at least there's an attempt at "checks and balances" the way laws are written.

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Gawker sites advocated harsh punishment for nude leaks of other celebrities. This is just holding them to their own standards.
If part of Gawker's strategy was that it could break the law because its victims lacked the financial resources to properly fund legal action, then Thiel is simply correcting a market failure. Ideally this would happen much more often.

However Gawker has also shown some mettle in resisting DMCA takedowns for stories that I do not consider frivolous mischief. Considering how pliant and officious the mainstream press is, Gawker's overall attitude is refreshing. But it's in poor taste to out someone's private business when doing so accomplishes nothing other than embarrassing that person.

The key ingredient for a respectable and effective press is a public that demands it.

The primary issue I have is that it's.... small.

Of all the things that he could use his money and power on, it's garden-variety petty vengeance.

Of course, it's his money and time. He can do whatever he wants with them. It just seems like poor prioritization.