The gating resource here was not capital," Thiel said. "The gating resource was...

The gating resource here was not capital," Thiel said. "The gating resource was the ideas and the people and executing it well. It's not like lawsuits haven't been brought in the past. It's something that's been done, so we were required to think very creatively about this space, what kind of lawsuit to bring." Most of the ideas do not stand up to scrutiny, or to Thiel's ambitions. A slap on the wrist from the FCC about affiliate commissions will accomplish little. Exploiting the financial misdeeds of the company would likely require an inside man, and this would be nasty, deceitful business. It wasn't just a question of which strategy might actually win, it was also figuring out which one could actually do real damage. "It was important for us to win cases," Thiel said. "We had to win. We had to get a large judgment. We did not want to bring meritless cases. We wanted to bring cases that were very strong. It was a very narrow set of context in which you could do that. You did not want to involve political speech, you did not want to involve anything that had anything remotely connected to the public interest. Ideally, our cases would not even involve the First Amendment at all." The First Amendment was unappealing not because Thiel is a libertarian, though he is, but because as a strategist he understood that it was Gawker's strongest and most entrenched position: we're allowed to say anything we want. It challenges the legal system and conventional wisdom where they are the most clearly established. Forget the blocking and tackling of proof and precedent. At an almost philosophical level, the right to free speech is virtually absolute. But as Denton would himself admit to me later, free speech is sort of a Maginot Line. "It looks formidable," he said, "it gives false confidence to defenders, but there are plenty of ways around if you're nimble and ruthless enough." That's what Thiel was doing now, that's what he was paying Charles Harder to find. Someone from Gawker would observe with some satisfaction to me, many years away from this period of preliminary strategizing from Thiel, that if Thiel had tried to go after Gawker in court for what it had written about him, litigating damages and distress from being outed, for example, he certainly would have lost. This was said as a sort of condemnation of the direction that Thiel ultimately did attack Gawker from. Which is strange because that was the point. The great strategist B. H. Liddell Hart would say that all great victories come along "the line of least resistance and the line of least expectation." John Boyd, a fighter pilot before he was a strategist, would say that a good pilot never goes through the front door. He wins by coming through the back. And first, that door has to be located."

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