It was in November December 12, 2016, four days after Donald Trump won his first presidential election. Aside from a few outliers (looking at you, Pierre Thiel), almost everyone in the tech world was shocked and appalled. At a conference I attended on Thursday, Facebook CEO Mark Zuckerberg said it was “quite a crazy idea” thinking his company had anything to do with the outcome. The following Saturday, I was leaving my favorite breakfast spot in downtown Palo Alto when I ran into Tim Cook, Apple’s CEO. We knew each other, but at that point I had never really sat down with him to do an in-depth interview. But it was a moment when raw emotions sparked all kinds of conversations, even among famously cautious journalists and executives. We ended up talking for which must have lasted 20 minutes.
I won’t go into details of a private conversation. But it won’t surprise anyone to hear what was mutually understood on that street corner: We were two people stunned by what had happened and shared the same unspoken belief that it was wrong.
I have thought about that day many times, including last year when Cook offered President Trump a sumptuous apple sculpture with a 24-karat gold base, and most recently this past weekend, when he attended the White House screening of the $40 million vanity documentary about Melania Trump. The event, also attended by Amazon CEO Andy Jassy (whose company funded the project) and AMD CEO Lisa Su, took place just hours after the Trump administration’s masked army in Minneapolis fired 10 bullets into a 37-year-old Department of Veterans Affairs intensive care nurse. Alex Pretti. Plus, a snowstorm was approaching, which would have provided a good excuse to miss an event that could very well haunt its participants for the rest of their lives. But there was Cook, celebrating a competitor’s media product, looking dapper in a tuxedo and posing with the film’s director, who hadn’t worked since he was accused sexual misconduct or harassment by half a dozen women. (He denied the allegations.)
Cook’s presence mirrors the behavior of many of his peers in the trillion-dollar tech CEO club, all of whom run companies highly vulnerable to the president’s potential wrath. During Trump’s first term, CEOs of companies like Facebook, Amazon and Google straddled a tightrope between opposing policies that violated their companies’ values and cooperating with the federal government. However, over the past year, their default strategy, executed with varying degrees of enthusiasm, has been to generously flatter the president and cut deals in which Trump can claim victories. These leaders also devoted millions of dollars to Trump’s inauguration, his future presidential library and the massive ballroom he is building to replace the demolished East Wing of the White House. In return, business leaders hoped to soften the impact of tariffs and avoid onerous regulations.
This behavior disappointed many people, including me. When Jeff Bezos bought the Washington Post, he was considered a civic hero, but now he’s transforming the venerable institution’s opinion pages into those of a White House cheerleader. Zuckerberg co-founded a group that advocated for immigration reform and wrote an opinion article lamenting the uncertain future of a young entrepreneur he was coaching who happened to be undocumented. Last year, Zuckerberg officially cut ties with the group, but he had already positioned himself as a Trump today.
When Googlers protested Trump’s immigration policies during his first term, co-founder Sergey Brin join their march. “I wouldn’t be where I am today, or the life I have today, if it wasn’t for a brave country that truly stood out and stood up for freedom,” said Brin, whose family fled Russia. when he was 6 years old. Today, families like hers are taken from their cars and classrooms, sent to detention centers and flown out of the country. Brin and his co-founder Larry Page built their search engine on the type of government grant provided by the Trump administration. can’t stand it anymore. Nevertheless, 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 the tech bigwigs fawning over Trump at a September news conference. Dinner at the White House where CEOs competed to see who could pander to Trump with the least sincerity. Another immigrant, Microsoft CEO Satya Nadella, once criticized Trump’s first-term policies as “cruel and abusive.” In 2025, he was one of those offer hosannas to the president.
