There are numerous moments over the past 30 years that one can point to as canaries in the coal mine, showing us what was coming: the breakdown of American politics and the ever-widening gap between the wealthy and everyone else.
The Hulk Hogan-Gawker trial is most certainly one of them.
Hogan’s (real name Terry Bollea) case against Gawker likely would not have happened without billionaire Peter Thiel, who spent millions bankrolling various lawsuits against the company, including this one. After Gawker published an article in 2007 outing him as gay, Thiel had seemingly made it his mission to put them out of business. And so he did, with a jury delivering a verdict in Bollea’s favor, awarding him $115 million in compensatory damages and $25 million in punitive damages. Unable to pay the judgment, Gawker filed for Chapter 11 bankruptcy protection and put itself up for sale (the case was eventually settled for $31 million).
Iconic sports site Deadspin wasn’t involved in the Bollea content at the heart of the trial, but it was included in that sale, which then became a whole other story.
The story of an impossibly wealthy billionaire (one who has openly expressed skepticism about democracy) sending the message that if you have enough money or power, you can control what is deemed newsworthy, especially when it comes to reporting about yourself, didn’t need any further scaffolding to be relevant to our current state of affairs.
However, it found some in perhaps the likeliest of places: The Epstein Files.
On Friday, the Justice Department released more than 3 million pages of files related to the investigation into convicted sex offender Jeffrey Epstein. Quite a few wealthy people in the sports world were found to have interacted with Epstein, some in incredibly disturbing ways. Also included was an email chain between Epstein and Thiel about the Gawker trial, in which Epstein seemed to say that he would have helped pay for the Gawker lawsuit had it not already been decided.
Among the batch of newly released emails from Jeffrey Epstein: Epstein telling Peter Thiel he would “gladly share…expenses for the Gawker suit.”
This was sent the day after @rmac.bsky.social and @mattdrange.bsky.social reported in Forbes that Thiel was behind the lawsuit that would bankrupt Gawker
— Ben Mullin (@benmullin.bsky.social) January 31, 2026 at 12:25 PM
“I would have gladly share[d] your expenses for the gawker suit,” Epstein wrote to Thiel on May 25, 2016, two months after Bollea was awarded $115 million.
Thiel responded with a smiley face emoticon.
As New York Times media reporter Ben Mullin noted, this email came a day after a Forbes report outing Thiel as the financial backer of the lawsuit.
Epstein’s desire to see Gawker bankrupted wasn’t just a case of one rich guy looking out for another rich guy. Gawker had done extensive reporting on Epstein, including a 2015 piece that referred to him as a “Pedophile Billionaire.” They were also the first to show details inside his “little black book,” including names and contact information for celebrities, politicians, media members, and others. Gawker had also created a primer on Epstein, four years before he would be arrested on federal sex trafficking charges.
Jeffrey Epstein’s reaction to Gawker’s publication of his little black book pic.twitter.com/hdigt1Aglb
— Ben Wieder (@benbwieder) January 6, 2024
Ultimately, Epstein’s money wasn’t needed to take down Gawker, but his appreciation for another billionaire, one he had many dealings with, for taking out a media company that did critical reporting on him, speaks volumes about the state of the American media landscape a decade later.
we said all along that they wanted Gawker dead not because we embarrassed a pro wrestler but because the Epstein story is one Gawker was covering a decade before most other people caught up & was just one of many stories exposing powerful people and their misdeeds
— Timothy Burke (@bubbaprog.xyz) January 31, 2026 at 12:31 PM
About Sean Keeley
Along with writing for Awful Announcing and The Comeback, Sean is the Managing Editor for Comeback Media. Previously, he created the Syracuse blog Troy Nunes Is An Absolute Magician and wrote 'How To Grow An Orange: The Right Way to Brainwash Your Child Into Rooting for Syracuse.' He has also written non-Syracuse-related things for SB Nation, Curbed, and other outlets. He currently lives in Seattle where he is complaining about bagels. Send tips/comments/complaints to sean@thecomeback.com.