Anthropic has bucked the rules of Trump’s Washington. It’s cost them.

At first glance, it might seem like the two frontier AI labs are in a similar position in President Donald Trump’s Washington. But nothing could be further from the truth. Anthropic has had a far rougher ride in Trump’s D.C. than OpenAI, or pretty much any other tech company.

Twice now the administration has taken unprecedented actions that pose a potentially existential risk to the startup, which is valued at $965 billion and which has filed paperwork for an IPO that is expected in the coming months. First, in April, the Pentagon labelled Anthropic a “supply chain risk” after it refused to accept contract language that the Pentagon was insisting upon. Then, two weeks ago, it got hit with export controls on Mythos as well as Fable, a version of the same model built for wider commercial release—after the discovery of a Fable jailbreak that could allow users to circumvent guardrails designed to prevent users from accessing Mythos’ full cyber capabilities.

Trump administration officials have repeatedly engaged in vitriolic attacks against the company, and its CEO Dario Amodei. Trump himself posted on social media that the company consisted of “leftwing nut jobs” who were trying to “strong-arm the Department of War” (the Pentagon, recently renamed by Trump) when the administration took the decision to label the company a “supply chain risk.” During the same dispute, Emil Michael, the undersecretary of defense for research and engineering, posted on X that “it’s a shame that Dario Amodei is a liar and has a God-complex.” Michael’s boss, defense secretary Pete Hegseth, called Amodei “an ideological lunatic” during an April Congressional hearing. Meanwhile, David Sacks, Trump’s former AI and crypto czar, who continues to hold roles on several government technology advisory committees, has repeatedly accused the company of running a “sophisticated regulatory capture” strategy based on fear-mongering about AI’s dangers. He has also said the company has an “agenda to backdoor Woke AI and other AI regulations” by supporting state-level AI laws.

During the recent export controls dispute, anonymous senior U.S. officials repeatedly sought to portray Amodei as arrogant and aloof, refusing to make himself available when the White House called. (Anthropic has disputed these accounts, saying Amodei was on the phone with the administration within an hour and fifteen minutes of the White House calling.) No other tech company has been subjected to these kinds of attacks from Trump administration officials.

At the heart of the conflict is a deliberate choice Anthropic has made: unlike nearly every other major tech company, it has refused to flatter or appease the White House. Washington insiders call it politically naïve. Anthropic’s employees and recruits, as well as some of the AI company’s customers, call it a feature. But investors may have other ideas. Continued hostility between the Trump administration and Anthropic could, at the very least, make it harder to sell public market investors on a stock listing. At worst, it could significantly hobble the company’s ability to continue to develop advanced AI models and undo the widespread enterprise adoption Anthropic’s existing AI models have enjoyed. This is the story of a company that has bet its political survival on being technically correct in a town that runs on loyalty.

There’s a standard Trump playbook. Anthropic isn’t following it.

When Trump was elected to a second term in 2024, a number of prominent tech CEOs had reason to be worried. Chief among them was Meta CEO Mark Zuckerberg. Zuckerberg had made the call to suspend Trump from Meta’s social media platforms after the January 6, 2021 U.S. Capitol attack. In response, Trump had branded Facebook “an enemy of the people” and called Zuckerberg a “criminal,” even threatening him with life imprisonment if he thought the CEO was trying to swing the 2024 election against him. What’s more, Zuckerberg had everything to gain if he could get Trump on side. Meta was facing a landmark federal antitrust prosecution that Trump, if he could be convinced, might pressure the Justice Department to drop or settle.

So Zuckerberg went out of his way to cozy up to Trump. He appointed a Trump loyalist Dana White to Meta’s board, ended content moderation in favor of a “community notes” system, and promoted Republican Joel Kaplan to head its global affairs team. Zuckerberg personally donated $1 million to Trump’s inauguration fund and Meta was among the companies donating to the construction of Trump’s $300 million White House East Wing ballroom. Meta also brought in Dina Powell McCormick, a former Trump deputy national security advisor with deep ties to the Trump family, to help lead the company’s AI strategy.

A similar playbook of flattery, donations, and the appointment of executives perceived as Trump allies to key government affairs posts has been followed by other tech CEOs who thought they might otherwise be in Trump’s crosshairs, such as Amazon founder Jeff Bezos and Apple CEO Tim Cook. According to a recent book by New York Times journalist Maggie Haberman, Trump ridiculed some of these tech CEOs for their obsequiousness in private but seemed to revel in it nonetheless—and there’s no denying that these tactics seem to have largely kept these technology giants from becoming government targets. (Although Zuckerberg failed in his efforts to get Trump to drop the antitrust suit against Meta, which is currently underway.)

Anthropic’s arch-rival OpenAI has also played this game. Its policy chief Chris Lehane grew up in Democratic political campaigns, but in the years before joining OpenAI became best known as a highly-effective hired gun for the crypto and tech industry in its fight against regulation. That earned him the admiration of many in Trump’s circle, who are also investors in crypto currency ventures or come from Silicon Valley’s libertarian circles, where regulation is seen as an impediment to innovation. Meanwhile, Greg Brockman, OpenAI’s cofounder and president, has emerged as the single largest donor to Trump Super PAC MAGA Inc.

Starting in a hole and continuing to dig

Anthropic, by contrast, started in a hole and kept digging. Amodei, Anthropic’s cofounder and CEO, had reportedly called Trump “a feudal warlord” in a now-deleted Facebook post urging friends to vote for Kamala Harris. His sister and fellow cofounder Daniela Amodei donated to Harris’s campaign and had, early in her career, worked for Hillary Clinton.

As if that weren’t enough, many of the Silicon Valley personas who ended up with key advisory roles in the Trump administration were on-record being critical of AI companies, including Anthropic and OpenAI, that had warned of AI’s potentially existential risks and were advocating for AI regulation in the years before they assumed official positions. In 2023, on his popular podcast, “All In,” Sacks, who would later become Trump’s AI and crypto czar, criticized the administration of then President Joe Biden for its AI policy, warning repeatedly that leading AI labs would push for regulations only they could comply with—the same “regulatory capture” charge he’d later level at Anthropic specifically. JD Vance, then still a Senator, told a Congressional hearing in July 2024 that he was worried about “some preemptive overregulation attempts that would frankly entrench the tech incumbents that we already have.” As Vice President, Vance has played a key role in tech policy deliberations.

Sacks and Sriram Krishnan, who would become a White House AI policy advisor, were also close associates of Elon Musk, having worked for him at Twitter/X. Musk, a key Trump tech advisor, had long accused Anthropic’s Claude of being “woke AI”—a line Sacks adopted, accusing the company of being run by “committed leftists.”

Rather than hire executives that might have tempered the Trump team’s predisposition to regard the company with animosity, Anthropic made a series of moves that antagonized them. It hired several outgoing Biden administration AI policy officials. These included Ben Buchanan, who helped architect Biden’s “diffusion rule,” a system of export controls on critical AI technology that Trump criticized and then dismantled when he took office; Elizabeth Kelly, who had headed the U.S. AI Safety Institute under Biden; and Tarun Chhabra, a coordinator for technology and national security on Biden’s National Security Council. In March 2025, after law firms Skadden and Latham & Watkins reached legal settlements with Trump, Anthropic pulled its legal work from the two firms. Amodei reportedly told staff he wouldn’t work with law firms that were caving in to what he saw as Trump’s assault on the rule of law.

This is not to say that Anthropic has refused to work with the White House altogether. The company notes that Amodei attended an energy event with Trump in Pennsylvania in the summer of 2025, where the President laid out his vision of U.S. energy and AI supremacy. Amodei also joined Trump on a trip to Japan in the fall of 2025. The company also voiced support for the White House’s AI Action Plan and participated in the White House’s AI Education Taskforce event as well as signing the White House’s Pledge to America’s Youth. In an October 2025 interview, Amodei told Fortune that the company has “lots of friends in the Trump administration” and that the company was more aligned with Trump than some of his advisors, such as Sacks, gave them credit for. In an earlier October blog post widely interpreted as a response to a series of highly-critical social media posts about the company from Sacks, who was angry the company was advocating for state-level AI regulation, Amodei went out of his way to say Anthropic concurred with Vance’s recent remarks that AI will have both benefits and harms, and that U.S. policy should try to maximize the benefits and minimize the harms.

But it was notable that Amodei was not invited to a White House dinner in September attended by leaders from other major U.S. tech companies and AI labs, nor was he among the tech CEOs Trump invited along on his state visit to the U.K. that same month.

And Amodei made clear he would not kowtow to the President. “When we disagree [with the White House], we’re going to say so,” Amodei told Fortune back in October. “If we agreed with everything that some government official wanted us to, I’m sure that could benefit us in business in some way. But that’s not what the company is about.”

Anthropic’s refusal to agree to a Pentagon contract that did not include explicit prohibitions on the U.S. military using their AI models for autonomous weapons or domestic mass surveillance won praise from many AI researchers, including those working for rival labs such as OpenAI and Google DeepMind. It also proved popular with consumers, especially when OpenAI did agree to a Pentagon contract that included language giving the U.S. military the right to use its AI models for “any lawful purpose.” Despite OpenAI including language in the contract highlighting that current U.S. policies or laws did not allow fully autonomous weapons or domestic mass surveillance, OpenAI faced a backlash, with many dropping OpenAI’s ChatGPT and downloading Anthropic’s Claude.

In an angry message that he posted to employees on Anthropic’s internal Slack in March, when the Pentagon designated the company a supply chain risk, and which then leaked to the press, Amodei said: “The real reasons [the Department of Defense] and the Trump admin do not like us is that we haven’t donated to Trump (while [OpenAI and its president Brockman] have donated a lot), we haven’t given dictator-style praise to Trump (while Sam has), we have supported AI regulation which is against their agenda, we’ve told the truth about a number of AI policy issues (like job displacement), and we’ve actually held our red lines with integrity rather than colluding with them to produce ‘safety theater’ for the benefit of employees (which, I absolutely swear to you, is what literally everyone at DoW, Palantir, our political consultants, etc, assumed was the problem we were trying to solve).” Amodei later apologized for the message’s tone.

Optics and personalities matter

Amodei’s diagnosis of the problem is likely correct. Yet the company seems to continually miscalculate the extent to which this dynamic will jeopardize its business. In the latest dispute over the danger posed by the jailbreak to its Fable model, Anthropic tried to minimize the risk the jailbreak posed, saying it only unlocked some of the underlying Mythos model’s powerful cyber capabilities and was not a “universal” bypass of Fable’s guardrails. Technically, the company was likely correct. More than 100 independent cybersecurity experts signed an open letter calling for the export controls on Fable and Mythos to be lifted, arguing that the jailbreak did not expose capabilities that were not already available from other AI models and that, furthermore, the ability to scan code for vulnerabilities was vital to cyber defenders.

That may be why Amodei felt justified in turning down the administration’s request to voluntarily pull Fable off the market, according to a story in Politico. But even if that was the right decision on a technical basis, it was a poor political one. According to the publication, Treasury Secretary Scott Bessent told Amodei as much, saying to the CEO he was making “a bad decision.”

The administration certainly seemed to relish the opportunity to punish Anthropic for its own previous statements that Mythos posed a serious threat. “You can’t tell everyone that your product might destroy the world and then not expect the government to be involved,” an administration official told Politico. “They’re politically naive.”

It was also probably unwise for Anthropic to choose an outside cybersecurity expert to vet the Fable jailbreak research—Luta Security founder and CEO Katie Moussouris—who was politically suspect in the eyes of Trump’s circle. Former White House deputy chief of staff Taylor Budowich posted on X to point out that Moussouris listed her pronouns on her X profile and was wearing a hat supporting Democrats in her profile photo. “These people really just don’t get it…,” he said about Anthropic’s choice of cyber expert. It didn’t help that cybersecurity expert Chris Krebs had been on X vouching for Moussouris’ abilities. Trump had fired Krebs in November 2020 after Krebs, who was then a top U.S. cybersecurity official, contradicted Trump’s claims about rampant election fraud and tampering with electronic voting machines in that month’s presidential election.

Anthropic has tried to adjust its lobbying efforts to be more Trump-friendly. Following its contract fight with the Pentagon, it belatedly engaged Ballard Partners, a Republican-leaning lobbying shop with a reputation for helping clients navigate Trump world. The company has also bulked up its own in-house policy team in D.C., including hiring a number of Republicans and former Trump officials. These include Chris Liddell, a former deputy chief of staff in Trump’s first White House, and Mary Croghan, who served in the Office of Cabinet Affairs, in Trump’s first term. Anthony Cimino, who is now Anthropic’s head of federal affairs, served on the Republican staff of the House Financial Services Committee. The company has also added Republicans, including former Missouri Senator Roy Blunt, to its national security advisory board.

Anthropic’s policy strategy is ‘on brand’ but off-kilter for Trump’s D.C.

But those efforts may be too little too late. And some Washington insiders say that given the way Anthropic has tried to position itself, not just politically but commercially, as an organization dedicated to AI safety, there may be a limit to its ability to bend in ways that will satisfy Trump’s team.

“I think they probably underestimated the necessity of building relationships and of the influence of money [in Washington],” Brendan Steinhauser, CEO of the Alliance for Secure AI, a Washington lobbying group that has been supporting AI regulation from the right, told Fortune. But he said that the real problem is essentially what Amodei diagnosed in his angry Slack message—other tech companies have been willing to do whatever the administration wants; Anthropic hasn’t.

“Anthropic, as a company, has a very clear brand and culture,” he said. “I think they’re just kind of acting in a way that is on brand for them, and Dario is acting in a way that is on brand for him.”

Steinhauser said that if the company were to shift its stance, it might alienate its employee base, which is a key constituency in a world where AI research and engineering talent is scarce and in high demand. It also, he said, might alienate some of the consumers that have flocked to Claude because Anthropic didn’t bow to the Pentagon’s demands.

“Is it putting them in some hot water with the administration? Yes. But I think it’s like a price that they’re potentially willing to pay to do what they think is the right thing to do,” Steinhauser said.

Stumbling toward a reset with the White House

Given these constraints, and given its lack of an in-house Trump whisperer, Anthropic has been hoping to depersonalize the conflict between Amodei and Trump’s team. After his initial involvement in phone calls with Trump officials two weeks ago, Amodei has let other Anthropic executives take the lead in negotiations with the White House. Anthropic first dispatched a team of technical executives, including one of its top cybersecurity researchers, Nicholas Carlini, Logan Graham, who evaluates AI models for risks, and Dave Orr, the company’s head of safeguards, to Washington, D.C., to meet with U.S. cybersecurity officials in the hopes of quickly convincing them to relax the export controls. The team has, according to a story in Politico, been working on a shared framework with the government for gauging exactly how much risk particular jailbreaks of model guardrails pose.

But, perhaps in belated recognition that the White House’s objections to Anthropic’s models are as much about politics as technical risks, Anthropic has also designated Tom Brown, an Anthropic cofounder who has been heading up the company’s efforts to secure enough computing capacity for its business, and Sarah Heck, the company’s new head of policy, who served on the National Security Council during Trump’s first administration and was a career diplomat before that, to lead negotiations with the White House.

Those negotiations have started paying dividends, as the U.S. government’s decision to relax export controls on its Mythos model indicates, although the company still has not succeeded in getting the export controls on its Fable model, which it was no doubt counting on to generate a good chunk of revenue, lifted.

Anthropic is realizing, belatedly, that being right is not the same as winning—not in Trump’s Washington.