As a fan of irony (and wrinkly, for you nasty youngsters), there was no question but that I had to write about Gawker’s follow-up post to the critically important question of whether Donald Trump’s hair was a weave.  What makes this too deliciously ironic to pass up?  It is the quintessence of both sides of the Gawker Dilemma.

On the one hand, Gawker has demonstrated that its position in the media is to be trivial, unserious, salacious and . . . no, that covers it. If those who hate Gawker for being Gawker, and ripped it a new asshole for airing content that millions of people want to see, and millions feel is “inappropriate” because they conflate their sensibilities with law, needed validation, you just handed it to them on a silver platter. Because Trump’s hair matters?

We all laugh at his hair. We’ve been laughing at his hair for a long time. But it’s just funny. We can all see his hair without you, Gawker. If this is what you call investigative reporting, then you’re the joke your haters claim you are. Was that what you were trying to prove, that you are the asshole of journalism? Well done, then.

But then came the letter.

But if you were under the impression that praise-worthy journalism is somehow inoculated against campaigns like Thiel’s, you’d be mistaken. Last week, Thiel’s lawyer-for-hire, Charles J. Harder, sent Gawker a letter on behalf of Ivari International’s owner and namesake, Edward Ivari, in which Harder claims that Feinberg’s story was “false and defamatory,” invaded Ivari’s privacy, intentionally inflicted emotional distress, and committed “tortious interference” with Ivari’s business relations. Harder enumerates 19 different purportedly defamatory statements—almost all of which were drawn from several publicly available lawsuits filed against Ivari.

Harder’s demands included the immediate removal of the story from Gawker, a public apology, the preservation of “all physical and electronic documents, materials and data in your possession” related to the story, and, notably, that we reveal our sources.

Except that’s not “the letter,” but a description of the letter. The most Gawker would do is quote a tiny bit of the letter.

[We specifically demand that Gawker Media and its employees] immediately provide us with the name and all contact information for the unnamed “tipster” of the Story, so that we can serve that person with an immediate cease and desist letter to stop the spread of the false Story.

Why? Well, that’s the point of the follow-up post.

Harder goes on to threaten legal action over the story: “Your actions expose you to substantial monetary damages and punitive damages.”

Can you feel it? Can you feel that chill in the air? That’s the chill I warned about, not that there was anything particularly brilliant about my foresight, as the chilling effect was obvious to anyone not suffering from blind Gawker hatred.

It goes on for six pages. Ordinarily, we would publish the entirety of Harder’s letter, so readers can judge its merits themselves. (Gawker Media’s response can be read here.) But Harder claims, on the fifth page, that the document is “protected by applicable Copyright law and therefore may not be copied, published, disseminated or used by any person or for any purpose, other than internally at your company and its outside legal representatives.” Given Harder’s propensity to launch groundless lawsuits against us, we have decided not to invite distracting litigation over whether such publication is covered by the Fair Use doctrine, even though it plainly is. But the absurdity of Harder’s threats should not distract from the underlying mission of the man who pays him: To intimidate Gawker and its reporters from publishing true things about public figures.

Point one: Even though the claim, on page 5 of the letter, that the letter is copyrighted, and therefore may not be copied, is absurd on its face, Gawker won’t publish it because it will lead to “groundless lawsuits” against it.

Point two: When someone with really deep pockets can finance groundless lawsuits, the cost of defending makes the end result irrelevant.

Point three: If there is enough money funding a revenge campaign, you can bring enough suits in varying jurisdictions until you find one judge willing to go along. Gawker didn’t make this point specifically, but I did.

In crim law, we have the aphorism, “you can beat the rap, but you can’t beat the ride.” It’s a tool used by cops since forever. They arrest, you go to jail. Maybe you get a beating along the way. Maybe not. Maybe you have to pay for a lawyer. Maybe not. Case gets dismissed, or maybe not, but no matter. They taught you a lesson about respect. They won. You lost, even if you won. And there is never a guarantee you will win, no matter how right you may be.

But just like the angry defendant who raises these points, who is in the right at every turn, and who can’t believe that no one gets the problem that has been made so painfully clear to them, Gawker can’t bring its point home because it is a party to the problem.  It’s not that Gawker isn’t entitled to make its point, or that its points aren’t entirely legitimate, but that it is interested in the outcome. Self-interest blunts the impact of an otherwise valid point, and makes it inherently subject to attack.

That’s why people like me jump into these messes, even on behalf of a media outlet as dubious as Gawker.  Ken White did it in the LA Times. Not because Gawker isn’t goofy, or because he believes in Gawker’s journalistic mission. He doesn’t:

It’s tempting to side with the gloaters; I’m as disgusted by Gawker as the next guy, and I’m not above feeling a frisson of glee when bad people face consequences for their actions. But schadenfreude isn’t a 1st Amendment value. From a legal and constitutional perspective, even Gawker haters should be troubled by its fate.

The alternative is that Harder’s letter, with its “keep this letter secret or I’ll sue you again, assholes,” wins. Not because it’s legally correct. It’s not. It’s totally insane. But who wants to get sued by Harder’s strawman client, Ivari?  And he’ll do it, of this there is no doubt, as there is a billionaire in the wings throwing money at him to get Gawker, if not for the rap, then for the ride.

But let’s not forget, this is over Donald Trump’s hair. Oh, Gawker. You make it so hard. So very, very hard.