Trump Gets a Lesson in History–and the First Amendment

Court strikes down his effort to tell West Point what to think.

“If there is any fixed star in our constitutional constellation, it is that no official, high or petty, can prescribe what shall be orthodox in matters of politics, nationalism, religion, or other matters of opinion or force citizens to confess by word or act their faith therein.”

The words, among the most luminous in the history of American constitutional law, come from Justice Robert Jackson in his 1943 opinion in West Virginia State Board of Education v. Barnette, which struck down a state requirement that schoolchildren salute the flag and recite the Pledge of Allegiance.

Tuesday, a federal judge in White Plains had occasion to apply its logic to West Point, issuing a comprehensive rebuke of one of the Trump administration’s most heavy-handed assaults on academic freedom.

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Tim Bakken, the plaintiff in Bakken v. United States Military Academy, is a civilian law professor who has taught at West Point since 2000. In January 2025, within days of taking office, President Trump signed Executive Order 14185, directing the nation’s military academies to stop “promoting, advancing, or otherwise inculcating” theories deemed “un-American, divisive, discriminatory, radical, extremist, and irrational”—a list of adjectives so elastic it could mean whatever the administration needed it to mean on any given day.

The order’s specific mandates were as revealing as its amorphous prohibitions. Faculty were forbidden from teaching that America’s founding documents are racist or sexist. And they were required, affirmatively, to teach that America and its founding documents remain “the most powerful force for good in human history.”

West Point implemented the order through a new Academic Engagement Policy, DPOM 03-24, requiring civilian faculty to obtain prior approval from department heads before many external engagements. The policy subjected every word Bakken wrote or spoke within his area of expertise to administrative review and potential suppression if the content conflicted with Executive Orders or bureaucratic instruction.

A companion classroom directive, delivered orally by West Point’s Dean, told faculty to stop sharing their personal opinions while teaching.

In its reply to Bakken’s lawsuit, the administration offered a series of institutional arguments—ensuring consistent messaging, alerting leadership to faculty appearances, preparing officials for public questions—while also urging the court to defer to military judgment.

U.S. District Judge Cathy Seibel found every one of those justifications to be post-hoc rationalization, unsupported by evidence of any actual harm the policy was designed to cure.

The real purpose of the policy was to demonstrate, in the words of two of Bakken’s own West Point colleagues—one a departmental head and vice chair of the Faculty Council, the other the head of his own department—“radical compliance” with the new administration, in other words, a way to protect senior West Point leadership by showing their obedience to Trump. The government never seriously disputed that characterization.

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Seibel, a George W. Bush appointee, granted Bakken’s motion for a preliminary injunction in an 85-page opinion that documented the several ways in which Trump’s efforts to enforce his own murky ideas of MAGA-approved speech ran afoul of the First Amendment.

Much of Seibel’s opinion addresses the government’s argument that Bakken had no business in federal court at all, that he was required instead to navigate the administrative remedies of the Civil Service Reform Act before any judge could hear him. Turning to the preliminary injunction standard, Seibel found Bakken had demonstrated, most importantly, a likelihood of success on the merits.

But the meat of the matter is Seibel’s First Amendment analysis, and its thoroughgoing rejection of the Administration’s scattershot, tendentious claims.

The constitutional principles at stake are the same ones Justice Robert Jackson articulated in a West Virginia elementary school in 1943. The government does not get to decide what is true, what is orthodox, or what ideas teachers at a military academy are permitted to share with cadets. And the prescription hardly serves the national interest in producing the next generation of military leaders.

Seibel’s reasoning here was dead on: West Point cadets “are not snowflakes who will somehow be harmed by learning about controversial issues or competing viewpoints.” On the contrary, the military and the nation need thoughtful, critical leaders who understand the world and can engage honestly with its complexity—in other words, the opposite of the brainwashed MAGA machines Trump wants the academy to turn out.

Even if the policy weren’t precisely wrong-headed, it would still fall. The governing standard here, which Judge Seibel meticulously applied, requires the government to bear a heightened burden when it imposes a broad, advance restriction on employee speech rather than responding to a specific incident after the fact. It must show that the harms it claims to be addressing are real, not conjectural, and that the restriction directly and materially alleviates those harms.

The administration’s vague submissions failed that test at every point. DOJ offered no evidence of any pre-existing harm the policy was designed to cure, and could not explain why less restrictive alternatives wouldn’t accomplish the same stated goals.

Seibel’s analysis was of a piece with the increasing rejection of the previous “presumption of regularity” that the Trump administration has squandered. She didn’t hesitate to second-guess the administration’s justifications and analyze not what the government said but what it did.

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Seibel concluded that the policy appeared to be “more a reverse-engineered justification” than a genuine attempt to connect the restriction to military necessity, and does little to undermine the evidence that the regulation is “an effort, in compliance with EO 14185, to force Plaintiff and other faculty to conform their speech to the President’s views.”

Ouch. That assessment is perfectly suited to Trump 2.0 and its Orwellian obsession with controlling every narrative.

Worse, that obsession has only coincidental overlap with the truth and history. What does it even mean to be forbidden from teaching that the Constitution, which forbade women and enslaved people from voting, was racist or sexist? How can a teacher possibly talk intelligently about American history under the Stalinist mandate of teaching that America and its founding documents remain “the most powerful force for good in human history.”

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There’s another classic First Amendment problem with the directive. The list of adjectives in Executive Order 14185 is so subjective and value-laden that it invests administrators with near limitless discretion in what they want to prohibit. A command to the nation’s military academies to stop “promoting, advancing, or otherwise inculcating” theories deemed “un-American, divisive, discriminatory, radical, extremist, and irrational” means whatever a loyal Trumper wants it to mean. It vests administrators with precisely the kind of unreviewable discretion the First Amendment forbids. Relatedly, it gives no notice to teachers of how they might fail to conform to the diktat.

Removed from its specific legal context, what this case was really about is the authoritarian’s reflexive ambition to prescribe orthodoxy. Jackson in 1943 condemned exactly that in Barnette: not just compelled salutes, but the government’s assertion that it has the power to determine what is true and require that all proclaim it. We shouldn’t be surprised at Trump’s ambition, which is exactly of a piece with his overall obsession with whitewashing the past and imposing a credo of all glory to him. Fortunately, Judge Seibel saw it for what it was and swatted it down. Chalk up another district court win for the good guys—and the Constitution.

Talk to you later.