Author gives behind-the-scenes look at book on Hulk Hogan/Gawker lawsuit

Ryan Holiday became more sympathetic to Gawker than he expected as he researched and wrote Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue, a book about the suit against the website’s publication of a sex tape, he told a National Press Club Headliners Book Rap on March 15.

“I came away easily being able to see both sides,” Holiday told former Club President Angela Greiling Keane, who interviewed him at the event.

In Washington to promote the book, Holiday shared insights from his in-depth research and interviews with some of the key players involved in the 2016 lawsuit, in which a jury found the website and media company Gawker liable for publishing a sex tape of wrestler Hulk Hogan with Heather Clem, the wife of radio personality Bubba Clem.

As a result, Gawker filed for Chapter 11 bankruptcy. Months later, it came out that Silicon Valley billionaire Peter Thiel had secretly funded the lawsuit in an effort to help Hulk Hogan bring down Gawker Media. After Gawker ran a story outing Thiel in 2007, Thiel conspired to get back at the media outlet, according to Holiday.

Throughout the lawsuit, Holiday covered the latest in the courtroom for the New York Observer. After the verdict, Thiel and Nick Denton, then-publisher of Gawker, both reached out to Holiday to share their side of the story.

“I was talking to both of them, which was unusual circumstances,” said Holiday. “Nick was willing to talk to me because Peter was talking to me. And Peter was willing to continue talking to me because I was talking to Nick. They both wanted their sides to be heard. They are both endlessly fascinated by the other. So similar, but so different. And once it got started, it was hard to stop.”

Holiday instantly knew he had a book on his hands; he just didn’t know which type of book, he said.

“Did I want it to be a general piece on media? A fact-driven story with analysis of what happened?” Holiday asked. “I finally settled on conspiracy, because that’s what I believe this was. There are a lot of conspiracy theories, but in this one, we have the person owning up to it, saying ‘Yes, I did this.’”

As the saga unfolded, Holiday said he could not believe how much information was not being reported.

“This was a story that the best reporters at the best outlets in the country took a stab at,” said Holiday. “Every major outlet has had someone cover this story, but that’s why it was so surprising to me, how much was not there.”

Ultimately he said he knew he had to turn what he calls this “almost Shakespearean, Count of Monte Cristo-type story” into a book.

He initially approached the book as “more of an epic history than a judgment,” Holiday said.

When Peter Thiel’s involvement was revealed, the story changed from superficial and hilarious chaos to a more serious threat to a story deserving of more attention, Holiday said, one that would lead people to question how a wealthy individual could destroy a publication that had once wronged him.

“As soon as Thiel’s involvement was revealed, I knew that no reporter would say, “Hey, what if Thiel is right?’” Holiday recalled. “I knew no one would say that. But because I’m outside the journalistic world, I thought, I can do this.”

A lively discussion with the audience revealed more of Holiday’s personal opinions on the case; that he felt Gawker crossed a line, its lack of editorial standards, but how he came out much more sympathetic to Gawker than he ever would’ve believed.

In the end, although the book departs from his type — Holiday, 30, has written seven books - the personal growth was worth the agonizing over the chronology and hours spent interviewing and poring over legal documents, he said.

“The stars aligned for me to write this,” said Holiday. “And I emerged a better writer because of it.”