After Minneapolis, tech CEOs are struggling to stay silent

It was November October 12, 2016, four days after Donald Trump won his first presidential election. With the exception of a few outliers (looking at you, Peter 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 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 bumped into Tim Cook, Apple’s CEO. We knew each other, but at that point, I had never sat down with him for an in-depth interview. But this was a moment when raw emotions were sparking all kinds of conversations, even among journalists and famously cautious executives. We ended up talking for 20 minutes.

I will not go into the details of the private conversation. But no one would be surprised to hear what was mutually understood on the street corner: We were two people distraught by what had happened and we shared the same unspoken belief that it wasn’t good.

I’ve returned to that day many times, certainly last year when Cook gifted President Trump with a shiny goofy sculpture with a 24-karat gold base, and most recently last weekend when he attended a White House screening of a $40 million Melania Trump documentary. 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 shot 37-year-old VA ICU nurse Alex Peretti 10 times. Also, there was a snow storm coming, which would have provided a good excuse to miss an event that might haunt attendees for the rest of their lives. But there was Cook, feted as a competitor’s media producer, looking sharp in a tuxedo, posing with the film’s director, who has not worked since six women accused him of sexual misconduct or harassment. (He has denied these accusations.)

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, the CEOs of companies like Facebook, Amazon, and Google walked a tightrope between objecting to policies that violated their companies’ values ​​and cooperating with the federal government. Last year, however, their default strategy, executed with varying degrees of enthusiasm, was to lavishly cajole the president and cut deals whose victories Trump could claim. These executives have also funneled millions toward Trump’s inauguration, his future presidential library, and the massive ballroom he is building to replace the destroyed East Wing of the White House. In return, business leaders hoped to mitigate the impact of tariffs and avoid burdensome 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 shaping that venerable institution’s opinion pages to resemble White House fan pages. Zuckerberg once co-founded a group that advocates for immigration reform and wrote an op-ed bemoaning the uncertain future of a young businessman he was coaching who happened to be undocumented. Last year, Zuckerberg officially cut ties with the group, but by then he had already positioned himself as a Trump sycophant.

When Google employees protested Trump’s immigration policies during his first term, co-founder Sergey Brin joined their march. “I wouldn’t be where I am today or live any kind of life I’m living today if this wasn’t a brave country that truly stood for freedom,” said Brin, whose family fled Russia when he was six. Today, families like his are being pulled from their cars and classrooms, sent to detention centers, and flown out of the country. Brin and fellow founder Larry Page built their search engine on the type of government grants that the Trump administration no longer supports. However, Brin is a Trump supporter. Alphabet CEO Sundar Pichai, himself an immigrant, oversaw Google’s $22 million contribution in the White House ballroom and was among the tech tycoons who fawned over Trump at a White House dinner in September where CEOs competed to see who could dishonestly please Trump. Another immigrant, Microsoft CEO Satya Nadella, once criticized Trump’s policies during his first term as “cruel and abusive.” In 2025, he was among those who paid tribute to the president.