Nick Denton stared at the six jurors before him and prepared for the worst. They had a choice: side with Denton, an English entrepreneur–turned–New York blog baron, or Terry Bollea, the American wrestling icon known as Hulk Hogan. Over the years Denton had built his small but influential company, Gawker Media, on the backs of countless reports that needled Hollywood celebrities, professional athletes, and Silicon Valley entrepreneurs. But when Gawker’s namesake website in 2012 published a grainy sex video featuring Hogan, the self-proclaimed “gossip merchant” went a bridge too far. Hogan sued in his hometown court in Florida, secretly backed along the way by PayPal cofounder Peter Thiel. And Thiel was willing to spend millions to show that subjects of Gawker Media’s scrutiny could fight back and drive Denton out of business.
In the courtroom, the foreman stood up and delivered a judicial body slam: a $115 million award in favor of Hogan. Three days later, on March 21, jurors tacked on another $25 million in punitive damages. (Gawker has appealed.) The sum was enough to force Gawker Media, and Denton, into bankruptcy. Thiel, an iconoclast who once described Gawker’s Valleywag website as “the Silicon Valley equivalent of Al Qaeda,” had won. A billionaire tech entrepreneur had managed to crush one of his industry’s most persistent critics.
Or so it seemed. A Fortune investigation into Gawker Media’s finances reveals that though Denton is down, he is not out. As the company’s websites assailed tech giants like Alphabet, Apple, and Facebook for byzantine schemes meant to reduce their tax burden, Gawker Media quietly played the same game. Our investigation reveals that Denton is as much a creature of the tech industry as he is a critic — and that Gawker’s slippery but legal tactics may, in the end, help Denton survive Thiel’s crusade with funds to spare.