One day in September 2014 the publisher of Gawker Media, Nick Denton, sent an e-mail to Peter Thiel, the Silicon Valley venture capitalist and billionaire. It could easily have been a message to a friend, or at least a kindred spirit, for, as many people who know them both have noted, the two have so much in common.

They are contemporaries: Denton turned 50 this past August, and Thiel 49 two months later. Both were born in Europe—Denton in England and Thiel in Germany. Both graduated from fancy universities—Denton from Oxford and Thiel from Stanford. Both made their fortunes in the digital world; in fact, it had brought them together in San Francisco a dozen or so years earlier. Both are gay, and both came out relatively late. Both are libertarians, and nonconformists, and visionaries, and science-fiction fans, and workaholics, and wonks. Both have resisted getting old, Denton by attitude, Thiel through human growth hormones. Both have a cultish kind of appeal. Both were wealthy still in 2014, though as winner of one of Silicon Valley’s greatest daily doubles—he co-founded PayPal and was Facebook’s first big investor—Thiel was exponentially more so, a fact that stuck in the ultra-competitive Denton’s craw. “Nauseatingly successful” was how Denton once described him. “Does Nick Denton wish he were Peter Thiel?” a headline on Denton’s own gawker.com once asked.

But, in 2007, Gawker’s Silicon Valley tributary, Valleywag, had outed Thiel, or at least Thiel thought it had. Both before and after that, Valleywag and Gawker had continued to ridicule Thiel, his investment decisions, his ideas, and his friends. It was such stories that had led Thiel, in 2009, to label Valleywag “the Silicon Valley equivalent of Al Qaeda” and to liken its writers to terrorists.

Maybe, Denton hoped, Thiel had moved on since then, or grown a thicker hide. So Denton drafted his note, which he read to me off his iPhone one day this past September. “Hey, Peter, this is a long shot but I’m going to try,” he began. “Would you get together for coffee when I’m next in San Francisco? We obviously have our differences, primarily over the politics of outing, and some of our coverage on Valleywag and Gawker has been needlessly gleeful. But your political views, while mockable, are a breath of fresh air. We have more in common than might meet the eye. I’d like to get some more constructive debate going between the New Left, which is represented rather heavily on New York editorial operations, and the Valley libertarians. The enemy is stagnation, and the vested interests that ensure stagnation, and yes, sometimes also the culture of Internet criticism that stymies original thought.”

“That’s all I got,” he concluded. “Let me know if there’s a conversation to be had.” He closed with “Regards, Nick.” He then read me Thiel’s response: “Nick, I’m not sure that a political conversation would be that constructive, but . . . ” Denton began, only to cut himself off. “I’m not going to share that with you,” he told me, at least not without getting Thiel’s permission. (“Just manners,” he explained.) He did show me what Thiel had written, but would not let me copy it down. I remember only that it was perfectly polite, and that whatever else he may have been thinking, Thiel had agreed to have that cup of coffee. “Nothing came of it,” Denton told me, and this is not surprising. For by the time he received that note Thiel had already begun pouring millions of dollars into a campaign to crush Denton and Gawker Media, using Hulk Hogan, of all people, as his cudgel. And by the time Denton and I spoke, Thiel had annihilated them all more completely than even he could have imagined, thanks to a Florida jury’s awarding Hogan $140 million in his Thiel-funded lawsuit last March, sending Gawker Media and Denton into bankruptcy and then killing off gawker.com altogether. It was the largest invasion of privacy payday ever against a major media company, and perhaps the first ever to bankrupt one. It was far more than Denton could handle, and it led in August to the fire sale of Gawker Media to Univision for $135 million. But Univision swallowed up only six of its seven Web sites; gawker.com, which generated 20 percent of its traffic and revenue and, according to Denton, 80 percent of its tsuris, was left to die. “Good riddance,” Thiel later said of its demise.