Headlines are buzzing with news about Gawker’s legal cage match with Hulk Hogan and the online publication’s recent and related bankruptcy. Some believe that this isn’t really the end for Gawker, even though the judgment awarded to the wrestling legend was more than double gossip magazine’s assets. But others say that the end of Gawker, at least as everyone knew it, happened before the plaintiff and defendant found themselves in the ring.

Gawker filed for Chapter 11 bankruptcy protection, which they hope will buy some time while they appeal the verdict, try to restructure and probably sell. And at the center of it all, PayPal founder, Peter Thiel appears to have finally won his own grudge match against Gawker owner, Nick Denton, which started brewing nearly a decade ago.

Gawker and Hogan Go Head to Head

Hulk Hogan has made some questionable life choices before, but he took extreme umbrage when the gossip magazine published a video that left little to the imagination. That led to an invasion of privacy civil suit against the Gawker, and the court decided in Hogan’s favor. It wasn’t just any win. The jury awarded Hogan $140 million in damages, a painful blow to the magazine.

A couple of years ago, the gossip publication was worth about $250 million. That’s according to Fortune magazine. But the Bankruptcy Petition showed assets at the time of filing between $50 million and $100 million. Hogan immediately became Gawker’s primary creditor. And with the likelihood of a court-mandated sale of the company, and Hogan situated to claim the proceeds, the magazine quickly filed for bankruptcy protection. It was granted.

Hogan Gets a Surprising Backer

The feud between Gawker and the wrestling superstar wasn’t as straightforward as it looked. There was much more boiling under the surface that didn’t involve Hogan at all. Peter Thiel, the founder of PayPal, had his own grudge against the publication. Nearly 10 years ago, the magazine published information about his private life that he didn’t authorize. So how did he pay them back? Slate magazine says he helped fund Hogan’s civil suit. Thiel wanted revenge, and he apparently got it in a roundabout way.

All of this sounds like gossip that’s as racy as anything Gawker might have published before. Unfortunately, advertisers pay attention to such scandals, and they can affect a publication’s bottom line. In 2014, during the Gamergate scandal, major brands such as Mercedes-Benz, Intel, and Adobe famously picked sides and broke their ad partnership tie with the publication.

Free Speech and Ad Revenue are Tough to Balance

Even with the Gawker verdict, magazines and newspapers enjoy free speech protection. But that protection doesn’t guarantee a continued ad partnership. Slate says that the Gawker case is “a calamity for free speech.” But some advertisers might not relish associating with a publication that pushes boundaries past daring and headlong into bad taste, whether or not it’s legal.

Denton acknowledged a quick tumble in revenue with the Gamergate scandal. And after the magazine published an exposé about a Condé Nast executive’s private life, Media Life says he had his editors remove the story. “He also took the opportunity to tell his staff that things at Gawker had changed,” they explained. “Advertisers don’t like it and suddenly, after years of being the cool kid laughing at all the publications that rein things in for advertisers, Gawker had to get its editorial department in line.” But it appears that Denton’s stance was too little and too late.

The takeaway in the Hogan versus Gawker showdown is that some courts believe free speech has limits, and pushing past them can cost you. It’s an expensive lesson for Denton. Not only has he watched major ad partners jump ship, but he’s about to lose the company that he built up from nothing.

Fortune says there’s an apparent agreement between Gawker and PCMag publisher, Ziff Davis, with Davis posed to buy Gawker properties. But because the sale will be court ordered, there’s no telling who will become the new owner. It could even be Thiel who ultimately walks away with the title belt in this smackdown.