Paypal co-founder Peter Thiel – a "conservative libertarian" who is opposed to democracy – is expected to donate $1.25m (£1.03m) to Republican presidential candidate Donald Trump's increasingly troubled campaign, according to sources reported by the New York Times.
The newspaper said a spokesman for Thiel declined to comment, and a spokesman for Trump's campaign did not immediately respond to a message for comment.
A controversial figure in Silicon Valley, many of Thiel's political views are thought of as running counter to the general ethos of the tech industry.
A member of the US Libertarian Party until 2016, Thiel describes himself as a "conservative libertarian".
In a 2009 post in the blog Cato Unbound, he wrote, "I no longer believe that freedom and democracy are compatible."
He donated to Ron Paul's unsuccessful nomination bid in 2007 and to John McCain's presidential campaign the following year.
The US tech industry has overwhelmingly backed Clinton, whose views on issues such as immigration and international trade deals are seen as being aligned with Silicon Valleys' priorities. Many major names in the sector are backing, and financially supporting, the Democratic candidate.
Luckey was unlucky in Trump
Elements of the US videogaming industry has also come out against Trump, when one of its leading figures was outed as a Trump supporter.
Palmer Luckey, a tech entrepreneur who founded the company developing the Oculus virtual reality system, met with heavy criticism from the tech and gaming industry after it was revealed he was secretly funding Nimble America group – a pro-Trump group.
Nimble America aimed to influence the election by creating anti-Clinton memes and other internet content.
Some game developers pulled support for the Oculus system, in protest at what they described as Luckey's financing of hate speech.
In August, Sheila Krumholz, the executive director of the Center for Responsive Politics, said that Clinton's campaign had received around $4m in donations from the US tech industry.
Earlier this year, Apple chief executive Tim Cook took a more political stance than Apple's previous CEO Steve Jobs, by holding a fundraiser for Clinton at the company. The tech magazine Wired magazine also made its first presidential endorsement by backing Clinton.
Going against the grain
Entrepreneur Joe Green – the founder of Causes, a Facebook app to help with donating to charities – said, "If there's any one principle Peter [Thiel] has, it's going against the conventional grain.
"The universal consensus in Silicon Valley is Donald Trump is bad for the country in many ways," Green added. "I didn't hear him [Thiel] argue why that's not true."
Thiel spoke at the Republican National Convention (RNC) in July this year, in which he declared on stage he was "proud to be gay" – making him the first speaker in the party's history to openly talk about being homosexual.
Thiel was outed by Gawker.com – a celebrity gossip blog which was owned by Gawker Media – in 2007. In May 2016, Thiel funded a lawsuit by former wrestler Hulk Hogan against Gawker.com, which effectively bankrupted Gawker.com. Gawker Media continues to trade.