Peter Thiel is usually the man behind the scenes in Silicon Valley.

He is the person who provided the first significant investment in Facebook and became a close confidant to its founder, but got featured in The Social Network for less than 30 seconds.

He is a core part of the incredibly influential PayPal mafia, who wrested control of the company from cofounder Elon Musk, but is still far less known to the general public than the Tesla and SpaceX CEO.

He is the cofounder of Palantir, one of the most valuable startups in the world, which itself operates largely under the radar to provide data tools to major corporations and intelligence agencies.

Thiel also occupied a key role behind the scenes of one of the most high-profile media court cases in recent memory.

Thiel told the New York Times he provided funding for wrestler Hulk Hogan's potentially devastating sex tape lawsuit against Gawker Media, making good on a nearly decade-long grudge against the online publisher. The admission came Wednesday after reports Tuesday evening in Forbes and the Times based on anonymous sources.

“It’s less about revenge and more about specific deterrence,” he told the Times. “I saw Gawker pioneer a unique and incredibly damaging way of getting attention by bullying people even when there was no connection with the public interest.”



Gawker Media's technology website Valleywag published critical and sometimes salacious stories over the years about Thiel or businesses he'd worked with, including one article publicizing the fact that Thiel is gay. Thiel made his feelings about Gawker known, comparing Valleywag to Al Qaeda.

Image: Dirk Shadd/The Tampa Bay Times

Nobody puts Peter in a corner

Thiel's alleged brazen attempt to punish a media company for unfavorable coverage quickly set off alarms about press freedoms and the relationship between the media and tech's billionaire class — all the more so considering Thiel serves on the board of Facebook, which is still dealing with a controversy over its possible manipulation of trending news topics.

Others have actually come to Thiel's defense, some using the hashtag #ThankYouPeter.

4/Rich folks have always been able to use big chip stacks to sue publications, but most pubs operate with higher ethics than Gawker. — jason (@Jason) May 25, 2016

Peter Thiel is a great American for funding the destruction of the Gawker machine. #ThankYouPeter — Alex Kirby (@AlexJKirby) May 25, 2016

While this episode is extreme, it is not entirely out of character for Thiel. He is famous in Silicon Valley for being a hyper-competitive, free-thinking, rabid libertarian with a sharp tongue full of contrarian viewpoints that are unconstrained by intellectual timidity or the existence of what one friend described as "intimate human emotions."

More to the point: Peter Thiel is a man who clearly does not believe anyone or anything should have power over him — not death, not competitors, not colleges, not governments, not political correctness and apparently not media outlets.

These are problems to be solved, or disrupted, in the parlance of Silicon Valley. All it takes is some combination of money and original, unconstrained thinking. Freedom, after all, is what matters most in his eyes.

On the subject of death, for example, Thiel has said simply: "I'm against it." He has invested millions in life extension projects and relies on a paleo diet and risky human growth hormones with the goal of living to 120.

He is an anti-government libertarian who is outspoken against what he sees as unnecessary taxation and regulations on businesses. In 2009, he wrote: "I no longer believe that freedom and democracy are compatible." As Musk once put it, “I’m somewhat libertarian, but Peter’s extremely libertarian.”

Thiel has even gone so far as to back The Seasteading Institute, a non-profit thinkthank whose whose stated goal is to build floating cities to get away from overbearing governments and "provide a machinery of freedom to choose new societies on the blue frontier."

Thiel has encouraged bright young minds to avoid the tyranny of college by offering $100,000 fellowships to would-be students to just "build new things instead." In his book Zero to One, Thiel encouraged businesses to build monopolies — a loaded word in tech and all business — rather than be just one of many competitors going after the same thing.

"Although many people describe themselves as contrarian, Peter is one of the few who have earned the distinction," Keith Rabois, a former PayPal colleague, once wrote of Thiel.

Rabois, like many of Thiel's colleagues, declined to comment for this article given the ongoing uproar over his reported involvement in the Gawker Media lawsuit.

A powerful man with powerful contradictions

As Thiel has recounted in his book and in numerous speeches, he initially set out to become a lawyer and was on the cusp of becoming a clerk for the Supreme Court before he got turned down.

"I was perfectly on track, but it turned out in retrospect my biggest problem was taking the track without thinking really hard about where it was going," Thiel said in a commencement speech this month.

Instead, he helped found PayPal a few years later, kicking off the online payment revolution, and netting himself tens of millions when the company was sold to eBay.

Soon after, he launched a hedge fund, made what may be the best tech investment in history by backing Facebook early and would go on to back prominent startups like Stripe, Quora and Oscar.

For all his business success, he remains a man of great and head-scratching contradictions.

He is a staunch supporter of liberal issues like legalizing gay marriage and marijuana, but also donated to Ted Cruz's presidential campaign and is now a registered delegate for Donald Trump.

Peter Thiel and Elon Musk during the PayPal days. Image: AP Photo/Paul Sakuma

He is known in Silicon Valley for an almost supernatural ability to time the markets, with Facebook founder Mark Zuckerberg once saying he listens closely to Thiel's advice on when to raise money and when to sell, according to The Facebook Effect. But he is also known for losing clients' money with his hedge fund,

He is a man who wants to live forever, but takes HGH even though it actually increases the risk of cancer. When asked about it, Thiel's response: "I'm hopeful we'll get cancer cured in the next decade."

And Thiel is a supporter of the Committee to Protect Journalists, which advocates for press freedoms, even as he effectively may be cracking down on the freedoms of one particular press outlet by funding efforts to sue it out of existence.

"Sometimes the people who break rules win and sometimes they push it too far," Thiel once said by way of criticizing Uber. In hindsight, perhaps Thiel's real criticism here wasn't about breaking the rules, but rather making sure you win.

UPDATED May 25, 2016, 7:10 p.m. PT to include Thiel's admission that he bankrolled Hulk Hogan's lawsuit against Gawker.

Have something to add to this story? Share it in the comments.