It was November December 12, 2016, four days after Donald Trump won his first presidential election. Apart from a few outliers (looking at you, Peter Thiel), almost everyone in the tech world was shocked and terrified. At a conference I attended this Thursday, Facebook CEO Mark Zuckerberg said it was a “pretty crazy idea” to think 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 met Tim Cook, Apple’s CEO. We knew each other, but at that point I had never actually met him for an in-depth interview. But it was a moment when raw emotions triggered all kinds of conversations, even between journalists and famously cautious executives. We ended up having a conversation that lasted probably 20 minutes.
I won’t go into details of the private conversation. But no one will be surprised to hear what was mutually understood on the street corner: we were two people stunned by what had happened and sharing the same unspoken belief that it was not good.
I have thought back to this day many times, and certainly last year, when Cook gave President Trump a gift shiny Apple sculpture in 24-karat gold, and most recently this past weekend, when he attended a White House screening of a $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 just 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. There was also a snowstorm approaching, which would have been a good excuse to miss an event that could haunt its participants for the rest of their lives. But there was Cook, feting a competitor’s media product, looking dapper in a tuxedo and posing with a movie director who hadn’t worked since was accused cases of inappropriate behavior or sexual harassment by six women. (He denied the allegations.)
Cook’s presence reflects the behavior of many of his colleagues in the trillion-dollar club of technology CEOs, all of whom run companies highly susceptible to the president’s potential wrath. During Trump’s first term, CEOs of companies like Facebook, Amazon and Google walked the line between opposing policies that violated their company values and cooperating with the federal government. But over the past year, their default strategy, pursued with varying degrees of enthusiasm, has been to flatter the president lavishly and strike deals where Trump can win. These executives have also donated millions 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, corporate leaders hoped to mitigate the effects of tariffs and avoid burdensome regulations.
This behavior disappointed many people, including me. When Jeff Bezos bought the Washington Post, he was seen as a civic hero, but now he’s transforming the venerable institution’s opinion pages into a White House cheerleader. Zuckerberg once co-founded a group advocating for immigration reform wrote a comment lamenting the uncertain future of a youthful entrepreneur he was training, who turned out to be undocumented. Last year, Zuckerberg formally cut the ties with the group, but by then he already had a position, among others, Trump today.
When Google employees protested Trump’s immigration policies during his first term, co-founder Sergey Brin he joined their march. “I wouldn’t be where I am today, or living the life I live today, if it wasn’t for a brave country that really stood out and stood for freedom,” said Brin, whose family fled Russia when he was 6 years old. Today, families like his are being dragged from 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 a government grant from the Trump administration no longer supports. Nevertheless, Brin is 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 figures who flattered Trump in a September meeting Dinner at the White House where CEOs competed to see who could flatter Trump the most disingenuously. Another immigrant, Microsoft CEO Satya Nadella, once criticized Trump’s first-term policies as “cruel and abusive” In 2025, he was among them offering hosanna to the president.