Mahmoud Khalil and the limits of liberty

Hundreds of protesters gathered on Wednesday morning outside Thurgood Marshall U.S. Courthouse in New York City, many wearing keffiyehs, a traditional Arab headdress for men that has become synonymous with pro-Palestinian causes. Others wore masks to conceal their identity. They carried signs that said, “Free Mahmoud Khalil,” “ICE off our campuses,” or “Stop U.S./Israeli Genocide of Palestinians Now.” At least a dozen demonstrators who refused to clear a road in front of the courthouse were arrested after scuffles with officers.

Inside the packed courtroom, the atmosphere was more restrained as U.S. District Judge Jesse Furman held a brief hearing on Immigration and Customs Enforcement agents’ Saturday arrest of Mahmoud Khalil.

The Trump administration has called for the deportation of Khalil, a recent Columbia University graduate and a leader in pro-Palestinian protests that have racked the university. In a court filing, Khalil’s attorneys describe him as “a Palestinian, born in a refugee camp in Syria, who holds Algerian citizenship.” He is married to a U.S. citizen, and his status as a legal permanent resident of the United States affords him the same constitutional rights as a citizen, including free speech. The Trump administration has claimed national security concerns outweigh those rights. “The secretary of state has reasonable grounds to believe that [Khalil’s] presence or activities in the United States would have potentially serious adverse foreign policy consequences for the United States,” a notice of removal said.

President Donald Trump wrote in a Monday Truth Social post that Khalil’s arrest was “the first … of many to come.” On Friday, ICE officials in Newark, N.J., said that they had detained Leqaa Kordia, who is reportedly Palestinian, for overstaying a student visa that was revoked in 2022 for what the Department of Homeland Security said was a “lack of attendance.” Kordia was also arrested last spring due to her participation in the pro-Palestinian protests at Columbia. DHS said that Columbia student Ranjani Srinivasan, an Indian national, self-deported earlier this week after officials revoked her student visa last week for “advocating for violence and terrorism.”

After Khalil’s detention, free speech advocates immediately voiced disapproval. In a Monday letter to Trump administration officials, the Foundation for Individual Rights and Expression acknowledged that campus demonstrations since the Hamas attack on Israel on Oct. 7, 2023, involved both constitutionally protected speech and unlawful conduct. But FIRE said the government’s statements thus far had not alleged that Khalil had committed any unlawful conduct.

In a Tuesday statement, FIRE was more direct: “This is America. We don’t throw people in detention centers because of their politics. Doing so betrays our national commitment to freedom of speech.”

The Trump administration contends Khalil did more than exercise his free speech rights. “This is an individual who organized group protests that not only disrupted college campus classes and harassed Jewish-American students and made them feel unsafe on their own college campus, but also distributed pro-Hamas propaganda flyers with the logo of Hamas,” White House press secretary Karoline Leavitt said on Tuesday.

Erielle Azerrad, a legal fellow at the National Jewish Advocacy Center, also noted Khalil’s actions and similar legal cases. In a recent City Journal article, she pointed to a 2018 federal appeals court ruling that upheld a decision by immigration judges that denied entry to an alien who had distributed flyers on behalf of Iranian terrorist organizations. “Publicly supporting a terrorist organization in a capacity ordinarily described as ‘speech’ may still render an alien deportable,” even if no monetary or other support is provided, wrote Azerrad.

Regent University School of Law professor Brad Jacob, a First Amendment expert, told me that, so far, the government has not produced evidence that Khalil was involved in anything more than First Amendment-protected political speech. Jacob said that there has been no showing that Khalil engaged in criminal behavior, encouraged others to do so, or incited immediate lawless action.

“He was just talking about how good Hamas is, how what they’re doing over in the Mideast is wonderful, how he hopes they exterminate all the Jews,” he said. “This looks like protected First Amendment speech, however offensive it might be.”

For doubters, Jacob suggested an analogy to which religious conservatives may be more sympathetic. “Just flip it around and have someone on a green card [a legal permanent resident like Khalil] who says something that’s viewed as totally offensive by a Democratic administration,” he said.

Jacob described a hypothetical situation with authorities detaining a non-citizen pro-life demonstrator who shouts “you’re murdering babies” to women entering an abortion center. “Then they say, ‘We’re revoking your green card. You have to leave the country,’ even though there’s been only First Amendment speech,” he said.

But Jacob agreed that much depends on how much authority the secretary of state has under the immigration laws and what evidence is sufficient to show that Khalil poses a national security risk or incited criminal behavior. Whatever court inherits Khalil’s case will decide those questions.

After booking Khalil at 2:20 a.m. Sunday morning in New York City, authorities moved him to a New Jersey detention center. While there, Khalil’s attorneys filed a writ of habeas corpus—a remedy for unlawful custody by the government—in the Southern District of New York, which includes Manhattan. Later that day, officials transported Khalil to an ICE facility in Louisiana, where he remains. On Monday, Judge Furman in Manhattan ordered the government not to deport Khalil until Furman could address the legal issues.

Those multiple transfers complicate the next legal steps for Khalil. In the Manhattan courtroom Wednesday, Assistant U.S. Attorney Brandon Waterman argued the court had no jurisdiction to rule on the petition filed by Khalil’s attorneys as Khalil was in New Jersey when the petition was filed. But Waterman said there could also be an argument that the case has to be heard in Louisiana, where Khalil is currently confined.

Furman ordered further briefing on the issue of location but seemed unlikely to keep the case in Manhattan. Late Wednesday evening, the government followed up its in-court argument, filing a motion to dismiss the habeas corpus petition or transfer it to the federal court in the Western District of Louisiana. It argued that, since the habeas corpus petition was not filed in New Jersey while Khalil was confined there, the New Jersey court never had jurisdiction.

On Thursday evening, Khalil’s attorneys filed an amended habeas petition that broadens their challenge. They ask the court not only to release Khalil but also to set aside what they call Secretary of State Marco Rubio’s “unlawful policy of targeting noncitizens for removal based on First Amendment protected speech advocating for Palestinian rights.” They also asked the court to release their client on bail.

Khalil’s detention comes as some on the extreme left and right of the political spectrum increase anti-Semitic attacks and universities grapple with how to respond. The Anti-Defamation League, an organization that tracks concerns about anti-Semitism, reports an “unprecedented increase” of anti-Semitic harassment and violence on college campuses since Hamas attacked Israel, documenting at least 1,200 incidents between Oct. 7, 2023, and Sept. 24, 2024.

At many universities across the country, pro-Palestinian student activists—often aided by off-campus advocacy organizations—not only protested what they called Israel’s “illegal occupation” but erected unlawful encampments that barred Jewish students’ access to libraries and other university facilities. Some also vandalized and occupied buildings and taunted and harassed Jewish students.

After a July hearing in a lawsuit brought by Jewish students at the University of California at Los Angeles, U.S. District Judge Mark Scarsi castigated university officials for their inaction. He ordered UCLA to prevent any future anti-Semitic zones on campus, and he found the encampment’s exclusion of Jewish students “abhorrent” and “unimaginable.”

ADL supports the administration’s deportation of Khalil, tweeting its appreciation for “the Trump administration’s broad, bold set of efforts to counter campus antisemitism.” That refers to Khalil’s detention and a Jan. 29 executive order addressing measures to combat anti-Semitism.

Since January, the Trump administration has launched Title VI investigations into discrimination at five universities and warned 55 other universities and colleges that a failure to address anti-Semitism at their schools will expose them to enforcement action—including funding cutoffs. Last week, the administration cut $400 million in federal grants to Columbia University.