It was November 12, 2016, four days after Donald Trump won his first presidential election. With the exception of a few suppliers (looking at you, Peter Thiel), almost everyone in the tech world was shocked and horrified. At a conference I attended that Thursday, Facebook CEO Mark Zuckerberg said it was “crazy” 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 ran into Tim Cook, the CEO of Apple. We knew each other, but at the time, I had never really sat down with him for an in-depth interview. But this was a time when raw emotions were starting all kinds of conversations, even among journalists and conservative celebrity executives. We ended up talking for what must have been 20 minutes.
I will not go into the details of the private conversation. But it shouldn’t surprise us that no one felt the same understanding in that corner of the street: We were two people who were surprised by what had happened and shared the same unspoken belief that it was not good.
I’ve thought back to that day many times, most notably last year when Cook gave President Trump a shiny 24k gold-based Apple gift, and most recently this past weekend when he attended the White House screening of a $40 million vanity documentary about Melania Trump. The event, which included Amazon CEO Andy Jassy (whose company sponsored the project) and AMD CEO Lisa Su, took place hours after Trump administration troops in Minneapolis put 10 bullets into 37-year-old Department of Veterans Affairs ICU nurse Alex Pretti. Also, a snow storm was coming, which would provide a good excuse to miss an event that would haunt the attendees for the rest of their lives. But there was Cook, who was picking up a competitor’s media product, who looked sharp in a tuxedo, and was posing with the film’s director, who had not worked since he was accused of sexual misconduct or harassment of half a dozen women. (He denied these allegations.)
Cook’s presence reflects the behavior of many of his peers in the $2 billion tech CEO club, all of whom run businesses that are at high risk of the president’s potential ire. During Trump’s first term, CEOs of companies like Facebook, Amazon, and Google walked the fine line between opposing policies that violated their company’s values and cooperating with the federal government. Over the past year, however, their default strategy, carried out with varying degrees of enthusiasm, has been to flatter the president and cut deals when Trump can claim victory. The administration also plowed millions into Trump’s inauguration, his future library, and the mock playroom he’s building to replace the demolished East Wing of the White House. In return, corporate leaders hoped to blunt the impact of taxes and avoid onerous regulations.
This behavior disappointed many people, including me. When Jeff Bezos bought the Washington Post, he was seen as a public hero, but now he’s shaping the opinion pages of that venerable institution into the White House cheerleader. Zuckerberg once co-founded an immigration reform group and wrote an op-ed bemoaning the uncertain future of an undocumented young entrepreneur he was mentoring. Last year, Zuckerberg officially severed ties with the group, but by then had set himself up as Trump’s part-time employee.
When Google workers protested Trump’s immigration policies during his first term, Google co-founder Sergey Brin joined their march. “I wouldn’t be where I am today or have the life I have today if this wasn’t a brave country that really stood up and stood up for freedom,” said Brin, whose family fled Russia when he was 6 years old. Brin and co-founder Larry Page built their search engine on a type of federal grant that the Trump administration no longer supports. Still, Brin is a Trump supporter. Alphabet CEO Sundar Pichai, also an immigrant, oversaw Google’s $22 million donation in the White House ballroom and was among the tech giants who flattered Trump at a September White House dinner where CEOs competed to see who could donate to Trump the most hypocritically. Another immigrant, Microsoft CEO Satya Nadella, once criticized Trump’s first-term policies as “cruel and abusive.” In 2025, he was among those giving hosannas to the president.
