Billionaire investor Peter Thiel has admitted to secretly funding wrestler Hulk Hogan’s lawsuit against Gawker Media. In an interview with The New York Times, Thiel called the suit “one of my greater philanthropic things that I’ve done.”

The news raises thorny questions about litigation financing and whether wealthy individuals ought to be able to use our court systems as a tool for revenge. (The site revealed in 2007 that Thiel is gay.) But what makes the situation even more complicated is the fact that Thiel sits on the board at Facebook.

In recent weeks, the social network faced accusations that it intentionally suppresses conservative news in its Trending Topics feature. Following its own internal investigation and a Senate inquiry, Facebook denied that any such bias exists.

Still, the Trending Topics debacle forced the American public to wake up to the fact that, for better or worse, Facebook plays an outsized role in the news they read everyday. Over the last few weeks, the company has scrambled to restore trust among its users, even inviting prominent conservatives to meet with CEO Mark Zuckerberg and Thiel, a known libertarian and Republican donor. Facebook subsequently updated its guidelines on Trending Topics and has renewed its vow to wield its power responsibly.

In the end, Facebook seemed to have escaped from that controversy relatively unscathed. The last thing the company now needs is a board member—a powerful one at that—funding revenge lawsuits against news outlets he believes have done him wrong.

To be clear, none of this is to say that Thiel has any direct influence over what does or does not appear on Facebook. The issue is not even whether lawsuits paid for by third parties are appropriate. The issue is whether it’s appropriate for someone who sits atop a company that claims to be a bastion for free speech to fund such lawsuits.

For critics who doubt Facebook’s motives, Thiel’s actions may look like yet another example of how the company has failed to acknowledge its position as perhaps the most powerful media outlet in the world. That position comes with certain ethical obligations, which include avoiding conflicts of interest at all costs. It’s hard to imagine a bigger conflict than spending $10 million to put a company out of business that depends on Facebook for survival.

Complicating matters even further is the recent news that Thiel is a pledged delegate for presumptive Republican presidential nominee Donald Trump, another litigious billionaire. Among his campaign promises, Trump has said he would “open up our libel laws” if he becomes president to make it easier to sue media outlets.

Neither Facebook nor Thiel responded to WIRED’s requests for comment.

At the heart of both the Thiel controversy and the Trending Topics debate is the issue of free speech, and whether Facebook is in fact a platform that protects free speech, regardless of ideology or personal vendettas. We’re entering an age in which new media companies are becoming more powerful than the traditional gatekeepers they wanted to unseat—but much less aware of the responsibilities that come with the power of the press.

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Peter Thiel’s Gawker Suit Is Another Free Speech Debacle for Facebook