Left inset: U.S. District Judge Rita Lin (U.S. District Court photo). Main: Defense Secretary Pete Hegseth meets with South Korea's Defense Minister Ahn Gyu-back, at the Pentagon on Monday, May 11, 2026, in Washington (AP Photo/Manuel Balce Ceneta).
A federal judge in California kicked off a hearing Thursday in Anthropic's lawsuit against the Trump administration by revealing her "preliminary impressions" that the government's case is not going well at all. By the end of the hearing, it appeared the DOJ had done little to change the jurist's mind.
U.S. District Judge Rita Lin made no secret of what she would ask about ahead of the hearing, a proceeding that could lead to a First Amendment win for Anthropic on summary judgment.
Once in court, she remarked at the outset, "I don't see additional evidence from the government really justifying what it did" and, "if anything, it seems like the record in some ways has gotten worse for the government" since she issued a preliminary injunction.
In the earlier stages of the case, the judge appointed by former President Joe Biden in 2023 blasted the "Orwellian" way President Donald Trump and Defense Secretary Pete Hegseth tried to sever ties with the AI contractor. The president and his cabinet official separately posted on Feb. 27 that Anthropic was "WOKE" and "sanctimonious" for believing its model Claude could not and should not be used for "autonomous lethal warfare and mass surveillance of Americans."
It happened after Anthropic CEO Dario Amodei made a public statement explaining why he believed the "two exceptions" to Claude's use matter at an "existential" level.
Trump responded by "directing EVERY Federal Agency in the United States Government to IMMEDIATELY CEASE all use of Anthropic's technology," and Hegseth heard the president's call loud and clear.
The secretary himself issued a "directive" — effective "immediately" — to ban other military contractors from doing business with Anthropic, on top of Trump's executive order permanently banning Anthropic from ever contracting with any agency.
Days later, on March 3, Hegseth designated Anthropic a "supply‑chain risk and threat to national security." One key problem for the government is that the judge has already gotten the DOJ to concede that the so-called "Hegseth Directive" not only had "no legal effect," but also "didn't reflect the immediate intent" of the Department of War.
That was the result of Lin's questioning months ago, after which she issued a lengthy preliminary injunction order blocking the Trump administration from "punishing" the company "for bringing public scrutiny to the government's contracting position" in an apparent act of "classic illegal First Amendment retaliation."
Against that backdrop, the judge informed DOJ attorneys James Harlow and Christian Dibble, and Anthropic lead attorney Michael Mongan, on Thursday that she still doesn't see "evidence" that the AI company posed a threat of sabotaging the Trump administration and national security beyond what the government called a "lack" or "breach of trust."
"Having reviewed the record that the parties have submitted on the cross motions for summary judgment, it appears to me to be largely the same as the record that I assessed at the preliminary injunction stage," Lin remarked. "I don't see additional evidence from the government really justifying what it did. If anything, it seems like the record, in some ways, has gotten worse for the government."
Thus, the first question Lin asked on Thursday was about the "Pickering framework" for "public-employee speech." The Pickering-Garcetti balancing test emerged from a series of decisions dating back to 1968. One of those cases concerned the rights of a public school teacher to comment on "matters of public concern" as a citizen compared to the state's interest in avoiding disruption in the classroom.
The judge wanted to know if the framework applies to "government contractors," like Anthropic, "when the government levies a punishment that goes beyond terminating the parties' contractual relationship or altering its terms[.]"
Lin tacked on a hypothetical, asking Hegseth's lawyers at the DOJ to "imagine" a future administration has a beef with a drone contractor hired for surveillance purposes but which "publicly refuses the administration's request to produce drones" that "can be used for lethal purposes."
The judge called it "really troubling" that the Trump administration was embracing a position that "seems at odds to me with the First Amendment," by "threatening to take away contracts from anyone who might do business with them" after "labeling them as subversive[.]"
She asked the DOJ to "imagine" that the government "just publicly announced that it is terminating every defense contract with anyone who's ever publicly criticized President Trump."
Would that be unconstitutional, the judge asked — apparently thinking it an "easy" question to say "yes" to.
"I mean, I think it would be an easy answer. I would think that the easy answer to that question would be yes. It's a First Amendment violation when the government's sole purpose is to stop public criticism of the president," she said.
"I think that's not this case," Harlow demurred.
"I'm surprised that you can't give a yes to what seems to me to be an easy question," Lin said again.
"And I think if there were to be a case that actually raised that very question, then I think that someone from the department could come up here and perhaps give that clear answer. But I think I've given you the best answer that I can," the lawyer went on.
Perhaps realizing the judge was still struck by the government's seemingly "quite extreme" position, Harlow acknowledged that if "that is the sole legitimate government interest, just saying that we don't like any public criticism," then he agreed it "would be very hard for the government to satisfy its burden."
The exchange stood out enough for Anthropic's lead attorney Michael Mongan to compliment the DOJ lawyer for his skill in advocating for his client under the circumstances.
"I think there's some staggering implications to the answer that you just heard about the hypothetical that the government could come out and say that any federal contractor who criticizes the federal government is subject to punitive actions, and that would be subject to Pickering," he said. "There are thousands and thousands of government contractors. That would lead to an immediate diminishment in their First Amendment rights."
"Now, we heard some careful answers, but not a very clear answer. I think I agree with your honor that the answer to that hypothetical is yes. That would obviously violate the First Amendment. I suspect that the reason that we're not getting a clear answer is that my colleague is a very good lawyer and appreciates that that could very well be the next case," he said.
Lin ended the hearing after an hour and a half, suggesting that her eventual ruling will take into account Trump's directive, Hegseth's directive, and the risk designation either "as a whole" or one-by-one "in terms of deciding whether the [government's] purpose was to retaliate."