Until this week, I hadn’t thought much recently about Scott McNealy, the early internet-era pioneer who cofounded Sun Microsystems alongside Vinod Khosla. McNealy is a Silicon Valley legend but has never seemed to care what anyone thinks of him—he once memorably dubbed Steve Ballmer and Bill Gates, his longtime foils at Microsoft, as “Ballmer and Butthead.” That malcontent energy was never more obvious than in the fall of 2019, when McNealy was revealed as the secret host of a blowout fundraiser for Donald Trump. It was, as it turned out, the sole fundraising event for the president in Silicon Valley during his reelection campaign.

I’ll admit that I have an ax to grind with McNealy: I had been trying to uncover the identity of the event’s host for several days, an expedition that naturally led me to McNealy’s doorstep. But I kept hitting a wall. McNealy’s assistant told me, when I inquired, that the billionaire was “on vacation in Lake Tahoe” and “pretty out of pocket due to cell service.” A few days later, when I drove out to Portola Valley, I saw a motorcade escorting Trump up the hill to McNealy’s estate.

I’ve moved on, don’t worry. But I was somewhat astounded last week when I learned that McNealy had given $50,000 to a pro-Trump super PAC led by Corey Lewandowski, becoming the highest-profile tech industry leader to back Trump after the events of January 6. Even Trump’s other big backers in the industry, such as Sequoia partner Doug Leone, have distanced themselves from Trump following the Capitol insurrection. Peter Thiel, formerly the president’s most high-profile tech supporter, hasn’t cut him a check in years.

I didn’t hear back when I reached out to McNealy to learn more about his F.E.C. filing, but if you scroll through his Twitter feed, you get a sense of his current political thinking—frequent retweets of Covid conspiracy theorists like Alex Berenson (before he was permanently banned),provocateurs like Mike Cernovich, and far-right leaders calling for audits of the 2020 election. McNealy has always been out there, but he has clearly gone a bit off the deep end.