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Peter Thiel's investment in Donald Trump doesn't seem to be paying off

Trump Holds Summit With Technology Industry Leaders Drew Angerer/Getty Images

For venture capitalist Peter Thiel, Donald Trump has turned out to be a poor investment.

BuzzFeed News reported on Monday that billionaire investor Peter Thiel, an early supporter of President Trump who served on his transition team, has been quietly criticizing the administration, going so far as saying at a January event: “There is a 50 percent chance this whole thing ends in disaster.”

These comments undermine Thiel’s effusive praise of Trump as someone who could break the Republican orthodoxy and provide a new path forward — and raise questions about how enduring Thiel’s support might prove to be.

Thiel was revealed in May 2016 as a Trump delegate to the RNC, endorsed Trump in a speech at the convention, and later outlined his support of Trump last September in an op-ed for the Washington Post, writing that “Trump’s heretical denial of Republican dogma about government incapacity is exactly what we need to move the party — and the country — in a new direction.” Thiel argued that the government was lacking in competence and propensity for innovation. But just about a year after publicly aligning himself with Trump’s campaign, Thiel described Trump’s administration as “incompetent” per BuzzFeed’s reporting.

As Timothy Lee wrote for Vox last summer, Thiel’s speech endorsing Trump at the RNC was couched in criticism of a government as ineffective and obsolete and a political scene focused on “fake culture wars” amidst an “economic decline.” For Thiel, Trump’s brash personality and lack of political expertise offered a way to break the molds of politics and government. BuzzFeed’s Ryan Mac reports that Thiel’s support of Trump apparently remained genuine as the campaign stretched into the fall, with Thiel citing tax reform as one of the few actual issues with which he aligned with Trump.

After Trump’s electoral victory, Lee wrote that Thiel’s endorsement, in hindsight, looked increasingly like a savvy investment for a venture capitalist known for “long-shot” investments, and whose data analytics firm, Palantir, is still in litigation regarding a multimillion dollar contract with the military.

Thiel was soon tapped to serve on the executive committee of Trump’s transition team, where he played a significant role in vetting candidates for various Cabinet appointments. As Mac noted, several of Thiel’s former colleagues, including Palantir’s Justin Mikolay, were hired by the Trump administration.

But at some point in the fall, Thiel’s confidence in Trump appears to have begun to waver: Though Thiel was publicly supporting and praising the candidate, according to Mac’s reporting for BuzzFeed, Thiel came across as less certain in private conversations, even as far back as just before Election Day:

But in at least one private conversation, Thiel admitted he didn’t have much confidence in either candidate. Whoever wins, he said, will likely be a one-term president, according to a person familiar with the discussion, with Thiel predicting that there would be a major financial catastrophe in the next four years.

At another event after the election, Thiel appeared to downplay the social policies of the administration to his liberal friends, noting his repeated belief that there was about a 50 percent chance of success:

According to two people in attendance, Thiel described the administration as a work in progress and discounted the suggestion that progress on social issues like gay marriage might be rolled back in the next four years. But these same people said Thiel tempered his enthusiasm with a caveat during one meal, remarking that "there is a 50% chance this whole thing ends in disaster."

More recently, Mac reports, Thiel has been described as “annoyed” by the Trump administration’s lack of movement on policy, and perhaps most damningly, told guests at an event in San Francisco in May that the Trump administration is “incompetent” after all.