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Why has Silicon Valley billionaire Peter Thiel spent upwards of $10 million funding third-party lawsuits against Gawker? If you believe his interview with the New York Times, Thiel’s willingness to bankroll litigation brought by Hulk Hogan and other plaintiffs stems from several posts, including a 2007 item about Thiel dating men, that have, in his words, “ruined people’s lives for no reason.” But the record of Thiel’s past comments paints a much more complicated picture of his motivation to end Gawker for good.

It is true, as Gawker Media CEO Nick Denton wrote in an infamous comment nine years ago, that Thiel was so anxious about Gawker’s coverage of his dating life that he tried everything in his power to have it suppressed: “I got a series of messages relaying the destruction that would rain down on me, and various innocent civilians caught in the crossfire, if a story ever ran.” At the time, the billionaire was a regular reader of Valleywag. “If I’m honest, I check it often, even when it’s somewhat embarrassing to me,” he told the German newspaper Frankfurter Allgemeine Zeitung in July 2007.

Two years later, though, Thiel had apparently come to terms with being in the spotlight. In a May 2009 interview, he called Gawker “purely destructive” and compared its staffers to Islamist terrorists, but acknowledged that the site wasn’t out to get him or treat him harshly. “I don’t feel that I’m being unequally targeted,” he explained. His criticism of Gawker hinged, instead, on the site’s built-in skepticism—bordering on disdain—for the burgeoning technology sector:

Did you ever imagine that you’d be the subject of conversation on gossip blogs like Valleywag, and how does that effect you, if at all?

[Laughs.] I’m not sure if I should answer this, but a couple of years ago, there was an article in New York magazine about Gawker Media, and the theme of it was sort of, everybody sucks, and the mindset that was being perpetrated ... it’s disturbing to me that there are people who are so angry out there.

And, later on: “It’s terrible for the Valley, which is supposed to be about people who are willing to think out loud and be different.” He would repeat this sentiment a few months later, in August 2009, when he met former Gawker editor Ryan Tate at Terroir, a wine bar in San Francisco’s SoMa neighborhood. “See?” he told Tate. “I’m willing to negotiate with terrorists.” In other words, he viewed Gawker’s coverage not in terms of particular individuals working in the technology sector—he wouldn’t have met with Tate if he did—but as an all-out attack on the idea of Silicon Valley itself.

Thiel has a very specific sense of how Silicon Valley investors should exert their power. And his vaunted prowess as an investor has not always been borne out by reality. As Gawker has noted over the past decade:

These stories, which are only a small sample of those Gawker has published about Peter Thiel, largely concern his professional life: Business ventures, political positions, and public statements. But as he noted to the Times, it was concern for his “friends” that Gawker had covered that motivated his secret legal assault: “One of my friends convinced me that if I didn’t do something, nobody would.”

And it is Thiel’s friends, broadly considered, that Valleywag made a business of holding accountable: The site’s motivating ethos was to report honestly on Silicon Valley’s businesses and personalities, and to trace out the distance between the meritocratic rhetoric and the actual way things work there. As former Valleywag editor Owen Thomas put it to the Times today, “Silicon Valley said it had ideals. All we asked was that it live up to those ideals.”

It was this persistent, nagging coverage—totally alien to a new billionaire class that had only known access-driven cheerleading from the likes of TechCrunch—that made Gawker and its sites, as Thiel put it, “terrible for the Valley.” Valleywag was creating a counter-narrative to the mythos of the free-market, death-destroying, Randian Übermensch that Thiel and his friends were peddling.

Silicon Valley’s hostility toward any critical coverage persists to this day. Last night, for example, a developer at Uber complained on Twitter that Gawker was “intentionally disruptive to acquisitions” and seemed designed to provide “fodder for NYC-focused disdain.” The refusal to engage in public relations or access journalism—the refusal to lubricate the flow of venture capital—is usually the mark of an outlet’s credibility. For Thiel and his peers in Silicon Valley, such a refusal amounts to repudiating their way of life.