Palmer Luckey might run a defense company now, but that doesn’t necessarily mean he’s done playing political games. The founder of virtual reality company Oculus is well-known for his fringe-friendly conservative politics and more recently for his status as an emerging Republican super-donor, funneling hundreds of thousands to the Republican Party and Donald Trump’s re-election campaign since the start of the year.

Which makes it all the more puzzling that Luckey recently made one donation to a Democrat, and not just any Democrat. Alexandria Ocasio-Cortez’s campaign for re-election in New York’s deep blue 14th District received $500 from Luckey in August, according to Federal Election Commission records. A second $500 donation, The Daily Beast learned, was also made this month but has yet to hit the FEC database.

"We first became aware of the donation when asked about it by The Daily Beast—as soon as we became aware of it we refunded the money,” Ocasio-Cortez campaign spokesperson Corbin Trent said of the contribution.

The Ocasio-Cortez campaign is puzzled about why a figure of Luckey’s political leanings would donate to the congresswoman, widely regarded as the progressive left’s most prominent new vanguard.

“I assume the majority of the people who donate to the campaign do so because they support her ideology and her policies and because she supports working class people,” Trent said. “I have no idea in this case."

Prior to donating to the activist left's torchbearer, Luckey contributed frequently to Republican candidates in both federal and state elections, to the Republican National Committee, and to Trump’s re-election campaign. The Daily Beast reached out to Luckey for some insight on the small donation—maybe he lost a bet?—but did not receive a response.

Luckey's irreverent approach to political life became infamous when in 2016 The Daily Beast reported that he bankrolled an organization to produce anti-Hillary Clinton memes, including a billboard near Pittsburgh picturing Clinton and the words “Too big to jail.” The series of events led to his ouster from Facebook, which he joined through the Oculus acquisition in 2014.

At Facebook, Luckey mostly kept his politics under wraps. After leaving the company, his efforts to bolster campaigns on the right have consistently ramped up, with flashy donations and cameos at Trump fundraising events. In July, Luckey spoke at a Trump Victory lunch hosted by Donald Trump Jr. and former Fox News host Kimberly Guilfoyle at Orange County’s ritzy Lincoln Club.

As an active conservative donor, Luckey has made regular at-limit contributions to Republicans since leaving Facebook in 2017. This year, those donations ramped up considerably: In March, Luckey donated $200,000 to Take Back the House 2020, a PAC affiliated with House Minority Leader Kevin McCarthy. In April, Luckey donated $106,500 to the Republican National Committee. That same day he chipped in $150,000 toward the Trump Victory fund.

Prior to donating to Ocasio-Cortez, Luckey recently contributed to her House colleagues including Elise Marie Stefanik (R-NY), Rep. Mike Gallagher (R-WI), and Michael Waltz (R-FL). He’s donated to Trump allies like Devin Nunes (R-CA) and even hosted an Orange County reelection fundraiser for Trump foe turned friend Ted Cruz (R-TX) in 2017. Last October, Luckey made a series of $10,000 donations to state Republican parties, including Kansas, Arizona, California, and Florida. Most of his candidate donations are for $2,700, the maximum amount an individual is allowed to contribute.

While his Facebook days are over, Luckey's flamboyant politics still pose a risk to his new company, Anduril Industries. Anduril is an emerging federal contractor that makes counter-UAS drones and high-tech border defense systems. Through contracts with Customs and Border Protection, Anduril’s suite of surveillance tools is currently monitoring the border between the U.S. and Mexico, where it has already led to a number of arrests. In August, The Daily Beast learned that Anduril’s tech is also part of a pilot program at the Canadian border.

While Anduril has leadership from both sides of the political spectrum, no other executives are nearly as politically energetic or financially engaged as Luckey himself. In spite of Luckey’s emerging role as one of tech’s most prominent Republican donors, Anduril is historically skittish about being identified as an explicitly Trump-friendly operation. After all, administrations come and go—and federal contracts with them.