Donald Trump, Mahmoud Khalil, and Free Speech Under Siege: “We’re in an Alarming Period”

“Do you believe in the First Amendment, Tom Homan?” yelled one incensed protester in the direction of the Trump administration’s so-called border czar. Homan was in Albany on Wednesday to try to convince New York lawmakers to make it easier for the federal government to detain and deport immigrants by doing away with protections that grant them sanctuary at the local level.

But the crowd gathered at the state capitol had other ideas. They were there to protest the disappearance and attempted deportation of Mahmoud Khalil, the Palestinian activist, green-card holder, and Columbia graduate student ICE detained last weekend over his role as one of the faces of student protests that rocked the university last spring—activities the Department of Homeland Security later claimed were “aligned to Hamas,” whatever that means.

As Homan walked away, the protester, who happened to be Zohran Mamdani, a state representative and New York City mayoral candidate, kept yelling questions at him, all while being held back by a state trooper: “How many more New Yorkers will you will you charge without targeting?” Homan didn’t answer. But standing alongside lawmakers on the same day, he made clear that “free speech has its limitations.” Pressed during an interview aired Thursday with NPR’s Michel Martin, DHS’s newly confirmed second-in-command, Troy Edgar, wouldn’t even say whether criticism of the government was a deportable offense.

And there it is. Hardly a week after Donald Trump declared to a joint session of Congress that he “brought back free speech in America,” his White House and the broader administration have shown their true colors: Through a series of crackdowns, executive orders, announcements, and other enforcement actions, they’ve turbocharged what can be fairly described as one of the greatest assaults on the First Amendment in modern history, harkening back to McCarthyism.

Except the ringleader this time is not a senator spreading fear about left-wing activism, communism, and un-American activities from his perch in Congress. It’s the president of the United States, armed with the full force of state power to go after political adversaries, protesters, dissenters, news organizations, immigrants, law firms, and institutions of higher education deemed out of step with his policies, priorities, and vision for the world. “We’re in an alarming period to say the least,” Lee Bollinger, a First Amendment scholar and former president of Columbia University, tells me. (Out of deference to the current leadership, he declined to address the current troubles at Columbia, which in many ways is ground zero for the Trump administration’s multipronged offensive against student activism and academic freedoms.)

The targeting of Mahmoud Khalil is revealing of how the government is pulling out all the stops to add a veneer of legality to its targeting campaign. On paper, at least, Khalil’s offense appears to be little more than not falling in line with the administration’s stance on the Israel-Hamas war that has ravaged Gaza. “The Secretary of State has determined that your presence or activities in the United States would have serious adverse foreign policy consequences for the United States,” reads the charging document initiating deportation proceedings against Khalil, which notes that “he refused to sign” it.

What are the “serious adverse foreign policy consequences” of Khalil’s activism? The administration hasn’t said. “The allegation here is not that he was breaking the law,” one unnamed White House official told the Free Press.

Yet Trump has proudly trumpeted the arrest, which he said was “the first arrest of many to come,” as if to suggest that Khalil’s views or involvement in the Gaza solidarity encampment on campus are themselves the crime. A day after that pronouncement, the White House press secretary, Karoline Leavitt, all but confirmed the reason Khalil and the university, from which he’s set to graduate in May, were made examples: Columbia, in the administration’s view, hadn’t done enough to identify people “engaged in pro-Hamas activity,” which in turn served as a warning to everyone else: “We expect all America’s colleges and universities to comply with this administration’s policy.”

The government’s invocation of the secretary of state’s authority to cancel Khalil’s status as legal permanent resident, which still must be approved by an immigration judge, is breathtaking in its own right. It relies on a section of the federal immigration code that would allow Marco Rubio to pick and choose the messengers and messages the administration deems contrary to the national interest. The former Florida senator has forcefully denied that the administration’s moves against Khalil have anything to do with free speech. “This is about people that don’t have a right to be in the United States to begin with,” he told reporters Wednesday. “No one has a right to a student visa. No one has a right to a green card.”

Stephen Vladeck, a law professor at Georgetown who has written about Khalil’s case, would only point to one other example, from the 1990s, of a secretary of state invoking the aforementioned provision in a deportation proceeding. Because of the law’s vagueness and overbreadth, it is only a matter of time until someone targeted by it, either in this or a future case, mounts a direct challenge to it. In the interim, his lawyers’ main concern, as reflected in a hearing on Wednesday in federal court in Manhattan, is getting their client released and back with his wife, who is eight months pregnant, while vindicating his right to advocate for his beliefs without repression.

Late on Thursday, as instructed by the federal judge who temporarily halted Khalil’s deportation, his lawyers filed an amended petition seeking his immediate release and return to New York. But they’re not just thinking about their client. They also want to invalidate any future attempts by Rubio to carry out the administration’s policy “of targeting noncitizens for removal based on First Amendment protected speech advocating for Palestinian rights.”

The case against Mahmoud Khalil is only the tip of the iceberg in the Trump administration’s onslaught against the First Amendment. The government’s abrupt cancellation of $400 million in federal funding from Columbia—and the threat to do the same at dozens of other colleges and universities—raises thorny questions about free speech and the latitude the government has to make a “value judgment” about the policies it wants to support. As it happens, the Knight First Amendment Institute at Columbia, which has been critical of Khalil’s arrest, has called the current state of the law “confusing” and “incoherent.”

Without an indication of what procedures were followed, let alone findings that could be challenged in court (as the law requires), the National Institutes of Health has linked some of these cuts directly to Columbia’s “continued inaction in the face of persistent harassment of Jewish students.” The escalation continues: In an extraordinary letter to Columbia leadership demanding “immediate compliance,” the Trump administration on Thursday outlined a series of repressive measures—from student expulsions to ramped-up law enforcement on campus to an overhaul of the internal disciplinary structure—aimed at ensuring university’s “continued financial relationship with the United States government.”

This is uncharted territory. And there’s no telling how the current Supreme Court, which has greenlit other funding restrictions in decades past, will view the current wave of budgetary pain the government is inflicting—or whether these schools will fold or fight back.

But anyone who has been paying attention to these and other rollbacks since the changing of the guard in Washington can have little doubt that the Trump administration is working overtime to wield federal funding as a political cudgel. Indeed, just as universities began feeling the wrath coming from Washington, last week, people who have chosen careers in public service learned that Trump signed an order purporting to withdraw student loan forgiveness promises for anyone working with organizations committed to causes that Trump doesn’t like, including those supporting immigrants or LGBTQ+ clients. If the purpose is to weaken legal resistance, the gambit may well work.

An even more striking example of this trend is the singling out of the law firm Perkins Coie, which has long represented Democrat candidates and successfully challenged Trump’s own attempts to subvert the democratic process during the 2020 election. In what was a clear act of retaliation for this work, the president restricted the firm’s lawyers from accessing government buildings and prevented various agencies from interacting with them. But Perkins Coie, rather than submit, quickly challenged this punishment as a violation of its rights under the First Amendment and other provisions.

Ruling from the bench on Wednesday, Judge Beryl Howell in Washington quickly blocked Trump’s order, noting that its impact “casts a chilling harm of blizzard proportions across the legal profession”—and that it “runs head on into the wall of First Amendment protections.” When the order was first announced last week, I observed that no respectable lawyer should’ve signed off on it, let alone defend it. I was validated when the Justice Department had to dispatch a political appointee, department chief of staff Chad Mizelle, whose own qualifications have been questioned in the past, to stand up in court and do so. (The law firms that declined to represent or express solidarity with Perkins Coie for fear of losing business in Trump’s Washington get no points for courage.)

Likewise, the Baltimore-based judge who blocked Trump’s executive orders barring diversity, equity, and inclusion efforts undertaken by federal contractors recognized that his ruling was necessary to “prevent the chilling effects” inherent from Trump actions. The judge said the orders amounted to viewpoint discrimination, which the First Amendment forbids—and that the plaintiffs who challenged them had “reasonable fears” that the vagueness of Trump’s mandates would prevent them from operating effectively.

And that’s not even counting Trump’s comments earlier this week that people who protest Tesla dealerships will be branded domestic terrorists. Or the White House’s decision to bar the Associated Press from its press pool for not kowtowing to Trump’s rebranding of the Gulf of Mexico. Or the Federal Communications Commission’s investigations of CBS, NPR, and PBS for coverage or decisions that are core to their identities. Or the purges of climate science and public health data, webpages, and other records that belong to all of us but the government has sought to suppress.

Litigation has curbed some of these abuses. But Bollinger, who has been at the center of major legal showdowns in the past, tells me that many of the areas where the Trump administration is pushing the limits of the First Amendment haven’t been tested yet in the courts and aren’t straightforward to resolve under current doctrine: “These are novel and new questions under the First Amendment.”

Doctrinal novelty or uncertainty never stopped even the most oppressed among us, across time and administrations, from embracing freedom of speech as a fundamental value. As happened during the first Trump administration, the courts can even follow the lead of the very organizers and immigrants’ rights activists being targeted. As goes Mahmoud Khalil, so go the rest of us. It is the people who have risen up to demand his release, with the First Amendment as their guide, who can have the final say on what its protections mean today.