• by Erik Sass , Staff Writer @eriksass1, May 26, 2016

“Revenge is a dish best served with a billfold,” is apparently the motto of tech investor Peter Thiel, who ponied up $10 million to fund the lawsuit brought by Hulk Hogan (real name Terry Gene Bollea) against Gawker for invasion of privacy after it published a sex tape without his consent.

It's all part of a grudge against the online gossip publisher dating back almost a decade.

The story starts in 2007, when Gawker outed Thiel – a co-founder of PayPal well known for his desire for privacy – as a homosexual. The post, titled “Peter Thiel is totally gay, people,” focused on Thiel’s refusal to acknowledge his sexuality in public — and the venture capital culture that prevented him from doing so.

Gawker founder Nick Denton asked in a comment on the article: “The only thing that's strange about Thiel's sexuality: Why on earth was he so paranoid about its discovery for so long?”

Although the article appeared fairly sympathetic (at least, for a post revealing someone’s sexuality against their wishes) its motivations were murky at best. Thiel also supports conservative causes, and reading between the lines, Gawker may have been trying to paint him as a hypocrite for failing to toe the “progressive” line.

Whatever their motivations, Thiel was evidently angry about having his private life bandied about for public consumption. Hee became even angrier when Gawker published unflattering information about some of his friends.

Of course, Gawker has made plenty of people angry, and more than a few of these have probably vowed revenge – but Thiel differed in actually pursuing it.

At some point, he instructed his lawyers to keep track of other celebrities and public officials besmirched by the gossip site. He had an eye to finding cases with courtroom potential, meaning situations where Gawker crossed a legal line.

On that note, Hogan’s case is actually just one of a number of lawsuits against Gawker funded by Thiel, who seems to care less about recouping losses (he is a billionaire) and more about sending message that online gossip, treated as a business, can ruin people’s lives.

To that end, his stated intent to force Gawker out of business – something founder Nick Denton acknowledged was a real possibility. (The site has dropped celebrity gossip and now focuses on politics.)

Thiel says he still supports freedom of speech, telling The New York Times: “I refuse to believe that journalism means massive privacy violations. I think much more highly of journalists than that. It’s precisely because I respect journalists that I do not believe they are endangered by fighting back against Gawker.”

So far, his tactics appear to be working.

The jury in the first trial awarded Hogan $140 million, although Gawker is appealing the judgment and the award may well be reduced. Nor is the revelation of Thiel’s support for Hogan, and his motivations for doing so, likely to substantially alter the outcome: This week a judge tossed out a request for retrial by Gawker’s lawyers.