Pick a side, you cowards.
In Trump’s Washington, America’s business leaders show the spinal fortitude of red licorice.
I’m a member of an encrypted group chat I probably shouldn’t be in anymore.
To be clear, I’m in a lot of chats I’ve muted or routinely ignore because I don’t have time. My life is fully focused now on countering corruption. So if it doesn’t have to do with that, I scroll past it. The college-friends thread has been neglected and so has the one of former Capitol Hill staffers. For some people, “group chats” have become the modern equivalent of the early 2000s email chain letter. An ignored nuisance.
But I recently took a renewed interest in this one. It’s a collection of CEOs and venture capitalists who discuss everything from robotics breakthroughs to American politics, and I was added years ago while advising companies on emerging tech and national security. I took a look at the chain, for the first time in a long time, because I was curious to see how these people were reacting to the Trump administration’s growing crackdown on AI companies.
I stumbled on something even more interesting.
Before I get to that, I’ll note that many of the people in the chat were pro-business Democrats who once groaned about Joe Biden’s executive order requiring developers of the most powerful AI models to share safety-test results with the government. Innovation-killing federal meddling, they called it. Trump ceremoniously threw out that Biden-era order on his first day in office. But since then, the Trump White House has undertaken far more heavy-handed moves than its predecessor, like blocking specific AI companies from releasing their products or labeling them a “national security risk.”
So I wanted to see: did Trump’s crackdown strike these techno-optimists as a big-government takeover?
Weirdly, as I scrolled through the chats from earlier this year, I saw that they seemed to welcome the new restrictions. Executives who fretted two years ago about Biden so much as talking about AI policy now praised Trump’s “foresight” in intervening in the marketplace. For a few of the group-chat participants, the motive was transparent. They’re deeply invested in rival firms or were delighted to watch a surging competitor brought to heel. Others, I’ll grant them, harbor genuine worries about the pace of progress.
But for most, it’s something else. Something darker.
What was striking to me was the general about-face. Plenty of these executives and startup vultures were as anti-Trump as it got during the president’s first term. They cheered for the tech-sector resistance or helped lead it, back when companies refused to enable a surveillance state or lend their tools to Trump’s agencies after those bureaucracies appeared to have been coopted to pursue the president’s political enemies. Now, many of these seem entrepreneurs are holding their tongues… or worse, applauding the ruler they once openly reviled.
I scrolled back through months of discussions I’d missed, since auto-disappear was not turned on. The tycoons and wannabe tycoons posted selfies from the White House, articles about “exciting” developments in the Trump administration like an explosion in defense-tech spending, and even favorable comments about the president’s garish America 250th celebrations. If anyone brought up controversies, they seemed to dance around criticism of the president or reached for comically cautious language. “Concerning,” one wrote in April of Trump’s threat to annihilate the Iranian people in a fiery genocide if their leaders defied him. Yes, concerning.
The more I scrolled, the more I felt like the chat was from a parallel reality. A space alien reading it would conclude the Trump administration was broadly celebrated, marred only by the occasional errant remark from its figurehead. Otherwise, all was well and good for the American people, their businesses, their allies, and the world writ large. (Except token costs. Token costs, the group-chat members fretted, were eating up a lot more of their budgets than expected.)
You’ve watched the public version of this yourself. You saw Tim Cook fawning over Trump in the Oval Office. You saw Bill Gates yucking it up with the president at a White House dinner. You saw Sundar Pichai and Mark Zuckerberg (men whose companies once took strident moral stands by defying this president) beaming through tech-summit photo ops. This isn’t even lobbying anymore. Lobbying, at least, was a professional necessity across administrations. This is more like the groveling pursuit of lapdog friendship with the president and his sycophants… a pursuit in which they’re thrown small morsels of mutual affection and expected to sit and drool and wait for more, while the White House wreaks havoc in the economy, raises prices, and creates chaos in global trade.
So let me go back to the Stockholm Syndrome group chat.
Why — in a private chat no less — were so many of them dancing in lockstep to the regime’s music when I knew, knew, they were registered Democrats and former anti-Trump diehards? The answer is a phenomenon rare in America but endemic to autocracies. It’s social fear. Many of these people are afraid of what happens if they say how they really feel. They’re afraid of being found out or snitched on, e.g. that a true believer in the mix, or a rival angling for advantage, will report their disloyalty to a White House that keeps blacklists of people and of insufficiently aligned companies.
I learned this early in Trump’s second term, when big-tech CEOs conveniently forgot they knew me the moment I landed on that blacklist. Despite the fact that some of them were my clients. The fear went beyond major companies. I realized how far the rot had actually spread when my legal defense fund couldn’t find a catering company to hire in a major city to serve soda at a fundraiser. When they found out the purpose of the event (to raise funds for an enemy of the president), these small businesses declined, fearing the possibility of ICE enforcement against their employees.
But a lot has changed since then. Popular defiance against Donald Trump has surged. Celebrities and news organizations have found their voices. Millions of Americans have filled the streets. Even MAGA diehards — from Marjorie Taylor Greene and Thomas Massie to Tucker Carlson, Megyn Kelly, and Tim Pool — have broken with the president in ways once unthinkable.
Yet business leaders seem like the last corner of society still holding out. They’re evidently the most tightly gripped by the president’s Darth Vader chokehold and wary to create daylight with a man who’s created a novel carrot-and-stick system for U.S. companies. While scanning the missives in the group chat, I felt like I was reading the text exchanges of Susan Collins clones, each cheerfully looking the other way until an atrocity forced out a murmur of “concern,” then moving briskly along.
History knows what to call these people. Germany’s industrialists convinced themselves that flattering the new regime was shrewd risk management. Today, they’re remembered as regime collaborators (and some ended up at Nuremberg). Russia’s oligarchs have similarly learned that obedience buys no safety; it just gets them a shorter leash. And when they stray, sometimes they get thrown out of windows.
The lesson is that the compliant never get total protection. They just get used. And then when history shines a light backward, they get remembered for it.
As the defiance to Donald Trump grows in this country, I wasn’t expecting much bravery from America’s business leaders. But I certainly had not anticipated the level of enduring cowardice. It’s not even that I want them all to join the resistance again. In the group chat, a few of those folks harbor true MAGA sympathies. Fine. But I want the rest to publicly pick a side and stop being so mealy mouthed or, worse, offering up fake praise for a man who they believe is an autocrat. At least then they’d stand for something.
Before you get too excited, I’m not going to “Jeffrey Goldberg” these people. They can learn the hard way what capitulation looks like. Not long from now, the most craven among them will start getting subpoenaed for donations to Trump’s ballroom… or get questions from the press about no-bid contracts they secured with Trump’s agencies… or experience the eventual release of emails showing them sucking up to Trump aides who might one day land in federal prison.
I’ll let karma run its course. In the meantime, I might post this essay in the thread. Then I’m leaving the chat.
Your friend, in defiance,
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