But Thiel also criticized the media's coverage of Trump's bombastic remarks. He said that while the media takes Trump's remarks "literally" but not "seriously," he believes Trump supporters take them seriously but not literally. In short, Trump isn't actually going to impose religious tests on immigrants or build a wall along the Mexican border, as he has repeatedly said, but will simply pursue "saner, more sensible" immigration policies.
"His larger-than-life persona attracts a lot of attention. Nobody would suggest that Donald Trump is a humble man. But the big things he's right about amount to a much needed dose of humility in our politics," Thiel said.
While the Silicon Valley tech corridor and suburbs around Washington have thrived in the last decade or more, many other parts of the country have been gutted by economic and trade policies that closed manufacturing plants and shipped jobs overseas, Thiel said, reiterating a previous talking point.
"Most Americans don't live by the Beltway or the San Francisco Bay. Most Americans haven't been part of that prosperity," Thiel said Monday. "It shouldn't be surprising to see people vote for Bernie Sanders or for Donald Trump, who is the only outsider left in the race."
Thiel later said he had hoped the presidential race might come down to Sanders and Trump, two outsiders with distinct views on the root cause of the nation's economic malaise and the best course of action to fix it. "That would have been a very different sort of debate," he said.
Thiel's prepared remarks seemed more of an admonishment of the state of the country today than a ringing endorsement of Trump's persona and policies. He decried high medical costs and the lack of savings baby boomers have on hand. He said millennials are burdened by soaring tuition costs and a poor outlook on the future. Meanwhile, he said, the federal government has wasted trillions of dollars fighting wars in Africa and the Middle East that have yet to be won.
Trump is the only candidate who shares his view that the country's problems are substantial and need drastic change to be repaired, Thiel said. Clinton, on the other hand, does not see a need for a hard reset on some of the country's policies and would likely lead the U.S. into additional costly conflicts abroad, he said.
A self-described libertarian, Thiel amassed his fortune as the co-founder of digital payment company PayPal and data analytics firm Palantir Technologies. He has continued to add to that wealth through venture capital investments in companies that include Facebook, Airbnb, Lyft and Spotify, among many others.
Thiel offered a full-throated endorsement of Trump at the Republican National Convention in July. During a six-minute prime-time speech, Thiel told millions of television viewers to disregard social issues that "distract" from the flagging U.S. economy and government's lack of innovation, which he described as more pressing concerns. "[Trump] is a builder, and it is time to rebuild America," Thiel said at the time.
He backed up that support earlier this month with a $1.25 million donation to political groups supporting Trump, putting Thiel among the largest single donors to the Republican nominee. In August 2015, Thiel gave $2 million to then-Republication candidate and fellow tech executive Carly Fiorina.
To call Thiel an anomaly in liberal-leaning Silicon Valley would be an understatement. Tech executives there have voiced ardent support for and opened their wallets to Clinton, including names like Apple CEO Tim Cook, Facebook COO Sheryl Sandberg and Google Chairman Eric Schmidt.
Facebook co-founder Dustin Moskovitz and his wife, Cari Tuna, pledged a staggering $20 million to political groups aligned with Clinton in September. Once fully allocated, the contribution will put the pair among the top political donors for the entire election cycle.
An open letter signed by 150 tech executives this summer stated plainly that "Trump would be a disaster for innovation," at least in part because of what they called anti-immigrant policies. Many of the tech industry's biggest companies were started by immigrants, including Thiel, whose family moved to the U.S. from Germany when he was an infant.
Thiel said he "didn't think there was going to be this sort of visceral reaction" in Silicon Valley to his support for Trump, saying that his past embrace of fringe ideas in business and technology were better received than political views similar to those of "half" the country.
"This is the first time I've done something that's actually conventional," Thiel said. "It's the first time I've done something big in my life that is just what half the country believes in and it's been the most controversial thing ever."
Thiel's remarks took place at the National Press Club in Washington, perhaps an odd choice of venue for a businessman whose relationship with the media is somewhat tenuous. The billionaire secretly bankrolled wrestler Hulk Hogan's invasion of privacy lawsuit against Gawker Media, which Thiel called a "sociopathic bully" during Monday's talk.
The lawsuit and resulting judgement helped push the company to bankruptcy earlier this year as retribution for a 2007 blog post that publicly outed Thiel as gay. The case caused much consternation in journalism circles about the ability of a wealthy man with a vendetta to take down a news outlet. Thiel said the circumstances of the Gawker case - a sex tape published without Hogan's consent - are unique and that he doesn't expect other wealthy individuals to follow his lead.
"Wealthy people shouldn't do that. I think if they tried they won't succeed," Thiel said.