Mahmoud Khalil’s Case Is About the Future of Free Speech

Despite some recent advances in his case against the Trump administration, Mahmoud Khalil remains confined for opposing genocide in Gaza — an imprisonment that makes a mockery of the First Amendment.

A demonstration in support of Mahmoud Khalil while a hearing takes place outside the Court in Newark, New Jersey, on March 28, 2025. (Kena Betancur / AFP via Getty Images)

The Trump administration’s McCarthyite deportation drive hit another roadblock on May 28. US district judge Michael E. Farbiarz found that a provision of the Immigration and Nationality Act, granting the secretary of state the power to expel noncitizens if the secretary determines they pose adverse consequences for US foreign policy, was likely unconstitutional when applied to Mahmoud Khalil. The once-obscure Cold War–era law has taken center stage as Secretary of State Marco Rubio has invoked it to retaliate against critics of Israel’s genocide in Gaza.

The ruling came as Judge Farbiarz weighs Khalil’s challenge to the constitutionality of his detention. Although the ruling is a step toward Khalil’s freedom and a rebuke to Donald Trump and Rubio, it leaves the permanent resident behind bars — for now. This is in sharp contrast to the cases of Badar Khan Suri, Mohsen Mahdawi, and Rümeysa Öztürk, similarly targeted by Rubio using the same Cold War provision, where federal judges have granted them bail pending a final ruling on their constitutional challenges. Although Khalil made a similar motion for bail on March 14, Farbiarz inexplicably has yet to rule on it.

Khalil’s prolonged purgatory is particularly cruel. When agents with Homeland Security Investigations, the law enforcement component of Immigrations and Customs Enforcement (ICE), arrested Khalil, his wife was pregnant. Since then, she has given birth. Khalil was not allowed to be present at the birth of his son, and the Trump administration sought to deny Khalil any contact visits with his newborn son. It took the judicial intervention of Farbiarz for Khalil to be allowed to hold his son for the first time.

The ruling came as the Trump administration appears to be doubling down. During a May 21 congressional hearing, Rep. Pramila Jayapal (D-WA), holding a copy of the US Constitution, confronted Rubio about his violations of the First Amendment. Rubio defiantly responded, “I will continue to revoke student visas.” Shortly after, Rubio announced a pause on all student visas pending increased social media vetting. The cable announcing the policy referenced two Trump executive orders believed to be the rationale for the attempted deportations of Khalil and others, as well as a new US Citizenship and Immigration Services (USCIS) of screening social media of those applying for legal status for “antisemitism.”

In the worldview of the Trump administration and many supporters of Israel, any support for the Palestinian people is deemed “antisemitic.” The Trump administration is developing a new, dystopian regime of mass social media surveillance in order to identify supporters of Palestinian rights to retaliate against. Today the penalization is the revocation of visas. But key architects of Trump’s onslaught on the First Amendment have made it clear that their goal is conflating all speech defending Palestine with terrorism. There is no reason to believe this ends with noncitizens.

As a result, Khalil’s legal challenge is more than one person’s fight for freedom. It is about the future of free expression in the United States.

Illegal Arrests and Kangaroo Courts

Khalil was born in a Palestinian refugee camp in Syria. During the anti-genocide protests at Columbia University in spring 2024, he was a negotiator between the students and the administration. As a result, anti-Palestinian organizations like the right-wing Betar began targeting him. Betar has since taken credit for the Trump administration’s actions against Khalil. (Along with the civil liberties organization Defending Rights & Dissent, where I work, I have filed a series of Freedom of Information Act requests to learn about the full extent of interplay between private blacklisters and the Trump administration in taking retaliatory action against Palestinian solidarity activists.)

As Khalil has sought to challenge both his deportation and his detention, new details have emerged about his arrest. Thanks to filings by his legal team, we now know that Homeland Security Investigations agents entered the private lobby of his apartment building and arrested him without any warrant. According to the Department of Homeland Security (DHS), Homeland Security Investigations was already conducting surveillance of Khalil on the day of his arrest to determine his daily patterns. While conducting this surveillance, they learned from a separate division of ICE that Rubio had made the determination that Khalil posed consequences for US foreign policy.

In the DHS’s version of events, after learning this they determined Khalil posed a flight risk and had to arrest him immediately without time to seek a warrant. The idea that Khalil, who was returning home from an iftar dinner with his wife at the time of his arrest and has since fought to stay in the United States, posed an imminent flight risk is simply not plausible.

Khalil has sought to challenge the constitutionality of his detention with a habeas petition in federal court. At the same time, removal proceedings against Khalil in immigration court have proceeded. Immigration judges are not part of the federal judiciary created by the US Constitution. They are part of the Department of Justice, the same body often seeking deportation. Sitting above individual immigration judges is the Board of Immigration Appeals. Members of this body are appointed directly by the attorney general, who can also modify or overrule their decisions. To say the deck is stacked is putting it mildly.

During the Clinton administration, the Board of Immigration Appeals issued a rare ruling on the foreign policy provision Rubio is using against Khalil. Under this ruling, once a secretary of state makes a determination under this provision, an immigration judge must find the party is removable. No defense is allowed. As a result, it is no surprise that during an April 11, 2025, immigration hearing, Jamee E. Comans found Khalil removable based solely on Rubio’s determination.

Following a determination of removability, immigration proceedings then move into a relief stage. At this stage, an immigrant found to be removable can put forward reasons why, in spite of this, they should not be deported. At a May 24 immigration hearing, Khalil and his lawyers made the case that he should be granted asylum. They also argued that the lawless nature of his arrest meant the proceedings should be terminated.

Police arrest a student during a protest across New York City demanding the release of Mahmoud Khalil, a Palestinian student activist and recent Columbia University graduate, on March 11, 2025. (Michael Nigro / Pacific Press / LightRocket via Getty Images)

In addition to citing the Rubio determination, the Trump administration has levied charges that Khalil misled immigration officials on his application for lawful permanent residence. This claim centers around the dates for which Khalil worked for the British government in Lebanon and claims he did not disclose his association with a pro-Palestinian student group at Columbia or the United Nations Relief and Works Agency for Palestine Refugees in the Near East. It is unclear why working with UN refugee relief or belonging to a student club would impact his application.

His lawyers have also denied the charge and attempted to submit evidence refuting it. Judge Comans refused to hear it during the May 24 hearing. Her rationale was that she had made no ruling based on this claim, and her decision that Khalil was removable was based solely on Rubio’s invocation of the Cold War law. She also warned Khalil’s lawyers not to argue with her, as they would lose.

Khalil’s case remains at heart about whether the secretary of state can unilaterally expel a lawful permanent resident from the United States based on his or her political speech.

Constitutional Challenges

Even though Congress has severely limited federal courts’ abilities to hear challenges to immigration removal proceedings, they still remain the best hope for those targeted by Trump and Rubio. That is why Khalil and others targeted have filed federal habeas petitions arguing their detention is unconstitutional.

Khalil’s lawyers have accused the Trump administration of trying to slow walk his federal habeas challenge while speeding up the immigration proceedings. The Trump administration has repeatedly challenged the jurisdiction of Judge Farbiarz to hear the case in federal court in New Jersey. The Third Circuit Court of Appeals denied a request from the Trump administration to take up their challenges. Khalil’s constitutional challenge thus continues in New Jersey, even as an immigration judge in Louisiana moves forward with removal proceedings.

As part of the challenge to his detention, Khalil has sought a preliminary injunction against the Trump administration. The injunction asks the judge to release Khalil from detention, vacate Rubio’s determination, and stop the Trump administration from “enforcing their Policy of arresting, detaining, and removing noncitizens who engage in speech in the United States supporting Palestinian rights or critical of Israel.”

In his late-night Wednesday ruling, Judge Farbiarz ruled Khalil is likely to prevail on his claim that the provision Rubio relies on is unconstitutionally vague when applied to Khalil’s activism. Farbiarz has ruled that an ordinary person reading the statute would never have known that it could apply to purely domestic speech. He also noted that only one federal judge has ever made a ruling on the provision. That ruling found the provision unconstitutional. (It was later overturned for unrelated reasons.)

While Farbiarz ruled Khalil is likely to prevail in his challenge to the Cold War provision, he ruled Khalil was unlikely to prevail on constitutional grounds in his challenge to the Trump administration’s claim that his “application for lawful permanent residence was allegedly inaccurate.” However, Farbiarz has never ruled on this ground, choosing to focus on the constitutionally suspect Rubio determination.

While establishing that Khalil is likely to prevail on the merits of his challenge is the first step to winning a preliminary injunction, Farbiarz has perplexingly demanded Khalil submit additional information to the court before a final ruling. While the ruling is a partial victory for Khalil, the continued kicking the can down the road, especially when other federal judges are granting bail, is dismaying.

Khalil may be a step closer toward freedom, but for now he remains locked away in a private immigration detention center in Jena, Louisiana. Not only is a father separated from his young child, but every minute Khalil remains confined for opposing a genocide casts a shadow across the First Amendment.