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.

Let’s give them the benefit of doubt. Since these CEOs have an obligation to shareholders, there was more than a fig leaf’s worth of justification for attempting to walk the much shakier tightrope of Trump’s second term. If this president perceives a slight, he goes into bully mode, using the full force of government against his perceived enemies. When Cook declined to join Trump on a trip to the Middle East, the president threatened to put higher tariffs on Apple. Cook eventually patched things up by offering Trump billions in domestic investments and giving him that now notorious gold trophy. Other powerful tech CEOs, many of whom had a long history of supporting Democrats, made similar concessions and fawning remarks, apparently deciding it was best to take one for the team.

But after Pretti’s murder, the tightrope finally snapped. Minnesota governor Tim Walz said it succinctly in a press conference on January 22: “We’re no longer having a political debate; we’re having a moral debate.” If there ever was a time for a reset, this was it.

Reading the room, some executives strained to put statements on the record making it clear they opposed killing citizens on the streets. (As of this writing, others, including Nadella, Pichai, and Zuckerberg, have avoided the room entirely and said nothing.) The first to crack, at least a bit, was Sam Altman, the CEO of OpenAI, who was facing pressure from his own employees. One particular source of unhappiness was the campaign contribution record of OpenAI cofounder and CTO Greg Brockman, who recently gave $25 million to a Trump super PAC.

Altman posted an internal Slack message that began with the assertion that loving one’s country meant pushing back when it overreaches. “What’s happening with ICE is going too far,” he wrote. “There is a big difference between deporting violent criminals and what’s happening now, and we need to get the distinction right.” But that was as far as Altman dared to venture. “President Trump is a very strong leader, and I hope he will rise to this moment and unite the country,” he continued. Really? If OpenAI’s GPT-5 had generated the hallucination that this president was interested in becoming a unifying force, Altman would probably issue a red alert that his model needed to be realigned with reality.

The most forceful statement came from OpenAI rival Anthropic. Company president Daniela Amodei wrote on LinkedIn that she was “horrified and sad to see what has happened in Minnesota.” She added, “Freedom of speech, civil liberties, the rule of law, and human decency are cornerstones of American democracy. What we’ve been witnessing over the past days is not what America stands for.” Considering that Anthropic has a lot to lose, including government contracts, it was a rare case of having a backbone. Even more encouraging, the CEOs of some 60 Minnesota-based companies, including giants like 3M and Target, released a letter on Sunday calling for federal and local officials to de-escalate tensions. The language was timid, but the point is that they did it in concert. It made one wonder why the big tech corporations aren’t acting collectively in their own interests, instead of capitulating alone.

Days after the Melania screening, Tim Cook also seemingly started to realize that silence, unlike his gift to Trump, was not always golden. In an internal memo that instantly leaked, Cook shared that he was “heartbroken” by the events in Minnesota and expressed sympathy with “everyone that’s been affected.” He also shared the news that he had “a good conversation with the president where I shared my views.” One can only hope that the views he shared were stronger than the tepid free-floating empathy expressed in his memo.

Until this year, Cook has cultivated an image of dignity and restraint throughout his tenure at Apple. He rewarded shareholders, honored the legacy of his famous predecessor, and introduced some really cool AirPods. Rumors have it that he will step down soon, and he deserves an honorable retirement. In his post-Apple years, and I hope there will be many of them, he will encounter many people at social events, small gatherings, and maybe even on street corners. Though those people might not say it out loud, some will certainly be thinking, “Why did you go to that Melania thing the day Pretti was killed?” He might even ask himself the same question. The weather would have been a great excuse to stay home.

This is an edition ofSteven Levy’sBackchannel newsletter. Read previous newslettershere.