It was November 12, 2016, four days after Donald Trump won his first presidential election. Aside from a few outliers (looking at you, Peter Thiel), almost everyone in the tech world was shocked and appalled. At a conference I attended that Thursday, Facebook CEO Mark Zuckerberg said it was “a pretty crazy idea” to think that his company had anything to do with the outcome. The following Saturday, I was leaving my favorite breakfast place in downtown Palo Alto when I ran into Tim Cook, the CEO of Apple. We knew each other, but at that point, I had never really sat down with him to do a deep interview. But this was a moment when raw emotions were triggering all sorts of conversations, even between journalists and famously cautious executives. We ended up talking for what must have been 20 minutes.

I won’t go into the particulars of a private conversation. But it will surprise no one to hear what was mutually understood on that streetcorner: We were two people stunned at what had happened and shared the same unspoken belief that it was not good.

I have thought back to that day many times, certainly last year when Cook gifted President Trump a glitzy Apple sculpture with a 24k gold base, and most recently this past weekend when he attended a White House screening of the $40 million vanity documentary about Melania Trump. The event, which also included Amazon CEO Andy Jassy (whose company funded the project) and AMD CEO Lisa Su, took place only hours after the Trump administration’s masked army in Minneapolis put 10 bullets into 37-year-old Department of Veterans Affairs ICU nurse Alex Pretti. Also, a snowstorm was coming, which would have provided a good excuse to miss an event that might very well haunt its attendees for the rest of their lives. But there was Cook, feting a competitor’s media product, looking sharp in a tuxedo, and posing with the movie’s director, who hadn’t worked since he was accused of sexual misconduct or harassment by half a dozen women. (He has denied the allegations.)

Cook’s presence reflects the behavior of many of his peers in the trillion-dollar tech CEO club, all of whom run businesses highly vulnerable to the president’s potential ire. During Trump’s first term, CEOs of companies like Facebook, Amazon, and Google straddled a tightrope between objecting to policies that violated their company’s values and cooperating with the federal government. In the past year, however, their default strategy, executed with varying degrees of enthusiasm, has been to lavishly flatter the president and cut deals where Trump can claim wins. These executives have also funneled millions toward Trump’s inauguration, his future presidential library, and the humongous ballroom that he is building to replace the demolished East Wing of the White House. In return, the corporate leaders hoped to blunt the impact of tariffs and avoid onerous regulations.

This behavior disappointed a lot of people, including me. When Jeff Bezos bought The Washington Post, he was seen as a civic hero, but now he is molding the opinion pages of that venerable institution into that of a White House cheerleader. Zuckerberg once cofounded a group that advocated for immigration reform and penned an op-ed bemoaning the uncertain future of a young entrepreneur he was coaching who happened to be undocumented. Last year, Zuckerberg formally cut ties with the group, but by then he had already positioned himself as a Trump toady.

When Googlers protested Trump’s immigration policies during his first term, cofounder Sergey Brin joined their march. “I wouldn’t be where I am today or have any kind of the life that I have today if this was not a brave country that really stood out and spoke for liberty,” said Brin, whose family had escaped Russia when he was 6. Today, families like his are being pulled out of their cars and classrooms, sent to detention centers, and flown out of the country. Brin and fellow cofounder Larry Page built their search engine on the kind of government grant that the Trump administration no longer supports. Nonetheless, Brin is a Trump supporter. Alphabet CEO Sundar Pichai, himself an immigrant, oversaw Google’s $22 million contribution to the White House ballroom and was among tech grandees flattering Trump at a September White House dinner where CEOs competed to see who could pander to Trump the most insincerely. Another immigrant, Microsoft CEO Satya Nadella, once slammed Trump’s first-term policies as “cruel and abusive.” In 2025, he was among those offering hosannas to the president.