On a Monday night NBC News segment, Anthropic CEO Dario Amodei expressed concern over “some of the things we’ve seen in the last few days,” referring to the violence of Border Patrol agents in Minneapolis.

Amodei focused on the importance of preserving democracy at home, both on NBC and in a post on X that specifically called out “the horror we’re seeing in Minnesota.” On NBC, he said he’s a believer in arming democracies to defend against autocratic countries, and that “we need to defend our own democratic values at home.” He added that Anthropic has no contracts with Immigration and Customs Enforcement (ICE).

Meanwhile, in an internal Slack message to OpenAI employees that got leaked to The New York Times, Sam Altman said, “What’s happening with ICE is going too far.”

“Part of loving the country is the American duty to push back against overreach,” Altman wrote. “There is a big difference between deporting violent criminals and what’s happening now, and we need to get the distinction right.”

Apple CEO Tim Cook also penned an email to his staff, which was leaked to Bloomberg, saying he was “heartbroken by the events in Minneapolis.”

Tech workers, including employees of both companies, have been calling on their chiefs to call the White House and demand that ICE leave U.S. cities in the aftermath of Border Patrol agents killing two U.S. citizens in Minneapolis. In an open letter, tech workers also urged their CEOs to cancel all company contracts with ICE and speak out publicly against ICE’s violence. 

Employees calling for CEOs to take action are encouraged and want more to join the ranks.

“We’re glad to hear the CEOs of OpenAI and Anthropic condemning the ICE murders,” the ICEout.tech organizers, whose identities remain unknown, told TechCrunch (before Cook’s email was leaked). “Now we need to hear from CEOs of Apple, Google, Microsoft, and Meta, all of whom have remained silent despite calls all across the industry.”

While Amodei, Altman, and Cook may be taking something of a stand — one in public, the other two internally — all three CEOs couched their statements with praise for Trump, as well. 

Cook said in his email that he had a “good conversation” with President Trump and appreciates “his openness to engaging on issues that matter to us all.” Apple employees were reportedly angry that Cook had attended an exclusive screening of a documentary about First Lady Melania Trump hours after ICE shot and killed U.S. citizen Alex Pretti.

Amodei applauded Trump’s consideration to allow Minnesota authorities to conduct an independent investigation into the shootings by federal agents after multiple videos of Pretti’s death circulated online. It remains to be seen if that investigation will happen, but a growing number of Republicans have begun to call for an investigation, as well. (Amodei’s sister and Anthropic’s president Daniela Amodei posted on LinkedIn that she was “horrified and sad to see what has happened in Minnesota. “What we’ve been witnessing over the past days is not what America stands for,” she wrote.)

In Altman’s message to his staff he also said he was encouraged by Trump’s more recent responses and said he hopes the president, “a very strong leader,” will “rise to this moment and unite the country.”

Altman assured them that OpenAI would “try to figure out how to actually do the right thing as best we can, engage with leaders and push for our values, and speak up clearly about it as needed.” Altman has yet to publicly criticize the administration’s immigration agenda, or how it is deploying Border Patrol agents into American cities. 

J.J. Colao, founder of PR firm Haymaker Group and one of the signatories on ICEout.tech’s letter, called Altman out for trying to “have it both ways” by calling Trump a strong leader, “as if the president bears no responsibility for ICE’s actions.” He added: “On net, I think his statement is helpful, but the performative tribute to the president does a lot to diminish it.”

Of course, the Trump administration’s current AI-forward policies have helped fuel explosive growth at companies like OpenAI and Anthropic over the past year; OpenAI raised at least $40 billion and is in talks to raise another $100 billion at an $830 billion valuation, and Anthropic has raised $19 billion and is in talks to raise another $25 billion at a $350 billion valuation.

Still, such words of praise for Trump is an about-face for Altman. In the lead up to Trump’s first term in 2016, Altman posted the following to his own blog:

“[Trump] is not merely irresponsible. He is irresponsible in the way dictators are…To anyone familiar with the history of Germany in the 1930s, it’s chilling to watch Trump in action.”

At that time, he called Trump a “demagogic hate-monger” who dangles the lie that he will “Make America Great by keeping us safe from outsiders” to distract from the fact that he actually has “no serious plan for how to restore economic growth.” Altman acknowledged that he took some risk by writing his post, and ended on a quote that has been attributed to Edmund Burke: “The only thing necessary for the triumph of evil is for good men to do nothing.”

“This would be a good time for us all—even Republicans, especially Republican politicians who previously endorsed Trump—to start speaking up,” he wrote.

And Amodei also appeared to be more passionate about his opposition to Trump allowing Nvidia to sell AI chips to China, calling the decision “crazy” last week during the World Economic Forum and likening it to “selling nuclear weapons to North Korea and [bragging that] Boeing made the casings.”

Whether these CEOs are doing everything that some among their workforce want them to do remains to be seen. Still, given what’s at stake for their companies, even internal and mild-mannered critiques are notable.

Spokespeople from Anthropic and OpenAI confirmed that neither company has contracts with ICE, but did not respond to TechCrunch’s requests for more information. TechCrunch has reached out to Apple.

This story has been updated with comment from J.J. Colao and to include Tim Cook’s leaked email.

Got a sensitive tip or confidential documents? We’re reporting on the inner workings of the AI industry — from the companies shaping its future to the people impacted by their decisions. Reach out to Rebecca Bellan at rebecca.bellan@techcrunch.com or Russell Brandom at russell.brandom@techcrunch.com. For secure communication, you can contact them via Signal at @rebeccabellan.491 and russellbrandom.49.