First Amendment

FIRE Says the Law Trump Is Using To Deport Mahmoud Khalil Is Unconstitutional. Trump's Sister Agreed.

As a federal judge, Maryanne Trump Barry said the provision is unconstitutionally vague. That's especially problematic when it is used to punish speech.

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For weeks, President Donald Trump and other federal officials have made it clear that they want to deport Mahmoud Khalil, a legal permanent resident of the United States, because they do not like what he had to say as an organizer of anti-Israel protests at Columbia University. Last week, the government began citing an additional justification, saying Khalil, who is married to a U.S. citizen, was not completely forthcoming about his employment history when he applied for a green card last March.

Those belated allegations, the government's lawyers say, provide an "independent basis" for deporting Khalil. "The new deportation grounds are patently weak and pretextual," one of Khalil's lawyers, Ramzi Kassem, told The New York Times, which notes that "the Trump administration appears to be using the new allegations in part to sidestep the First Amendment issues raised by Mr. Khalil's case." As a brief from the Foundation for Individual Rights and Expression (FIRE) shows, those issues pose a real problem for Trump's plan to expel legal residents he perceives as "terrorist sympathizers."

Immigration agents arrested Khalil in New York City on March 8 and briefly held him in New Jersey before taking him to a detention center in Louisiana. Last week, Jesse Furman, a federal judge in Manhattan, transferred the case, Khalil v. Joyce, to New Jersey because that is where Khalil was when his lawyers first challenged his detention. FIRE, joined by several other civil liberties groups, including the Rutherford Institute and the First Amendment Lawyers Association, therefore filed its brief in the U.S. District Court for the District of New Jersey.

The Trump administration does not claim Khalil has committed any crimes that would make him deportable. Rather, the government says he is "subject to removal" under 8 USC 1227(a)(4)(C)(i), which authorizes the deportation of "an alien whose presence or activities in the United States the Secretary of State has reasonable ground to believe would have potentially serious adverse foreign policy consequences for the United States." FIRE says that "Foreign Policy Deportation Provision" (FPDP), which Congress approved in 1952 as part of the Immigration and Nationality Act, is unconstitutional, and so is its application to Khalil or other legal residents whose views offend the government.

"The only court to address the FPDP's constitutionality (so far as we can find) held it unconstitutionally vague," FIRE says, citing Massieu v. Reno, a 1996 decision by a federal judge in New Jersey. "The range of circumstances that could warrant deportation" under the FPDP "is virtually boundless," the judge said. The law grants the secretary of state "unrestrained power," she noted, "authoriz[ing] a heretofore unknown scope of executive enforcement power vis-a-vis the individual with utterly no standards provided to the Secretary of State or to the legal aliens subject to its provisions."

The FPDP "provides absolutely no notice to aliens as to what is required of them," the judge added. "The statute represents a breathtaking departure both from well established legislative precedent which commands deportation based on adjudications of defined impermissible conduct by the alien in the United States, and from well established precedent with respect to extradition which commands extradition based on adjudications of probable cause to believe that the alien has engaged in defined impermissible conduct elsewhere."

Although FIRE does not mention it, the author of that opinion was President Trump's sister, Maryanne Trump Barry, who later served on the U.S. Court of Appeals for the 3rd Circuit. "I will never forget the many times people would come up to me and say, 'Your sister was the smartest person on the Court,'" Trump wrote on Truth Social after Barry died in 2023. "I was always honored by that, but understood exactly what they meant—They were right! She was a great Judge, and a great sister."

Barry, according to Trump, was by no means a "Radical Left Lunatic"—one of those "Crooked Judges" who are always trying to obstruct his agenda for political reasons. She nevertheless thought the statute on which he is relying to deport Khalil was unconstitutional. Although the 3rd Circuit later reversed her decision, its rationale was that the plaintiff had failed to exhaust his administrative remedies, not that Barry's take on the FPDP was wrong.

Using that "unrestrained" and "virtually boundless" authority to deport a legal resident based on the opinions he has expressed raises obvious problems under the First Amendment, notwithstanding Secretary of State Marco Rubio's insistence that Khalil's case "is not about free speech." FIRE argues that the deportation threat constitutes viewpoint-based discrimination, which is presumptively unconstitutional, and amounts to government retaliation for constitutionally protected speech. It says that would be true even if Khalil had expressed support for Hamas (which he denies) because "philosophical support for a terrorist organization (let alone mere overlap of certain political beliefs) is fully protected by the First Amendment."

Does it matter that Khalil is not a U.S. citizen? In the 1945 case Bridges v. Wixon, the Supreme Court held that "freedom of speech and of press is accorded aliens residing in this country." That case involved a longtime legal resident from Australia who was deemed deportable based on the allegation that he had been affiliated with the Communist Party.

"Once an alien lawfully enters and resides in this country, he becomes invested with the rights guaranteed by the Constitution to all people within our borders," Justice Frank Murphy wrote in a concurring opinion. "Such rights include those protected by the First and the Fifth Amendments and by the due process clause of the Fourteenth Amendment. None of these provisions acknowledges any distinction between citizens and resident aliens."

Trump's sister made the same point in Massieu. "Make no mistake about it," Barry wrote. "This case is about the Constitution of the United States and the panoply of protections that document provides to the citizens of this country and those non-citizens who are here legally and, thus, here as our guests."

At the height of the Red Scare in 1952, the Supreme Court nevertheless rejected the First Amendment claims of several immigrants who were threatened with deportation because they had been members of the Communist Party. But that decision in Harisiades v. Shaughnessy was based on an understanding of the First Amendment that the Court later repudiated.

"The claim is that, in joining an organization advocating overthrow of government by force and violence the alien has merely exercised freedoms of speech, press and assembly which [the First] Amendment guarantees to him," Justice Robert H. Jackson wrote in the majority opinion. "The assumption is that the First Amendment allows Congress to make no distinction between advocating change in the existing order by lawful elective processes and advocating change by force and violence, that freedom for the one includes freedom for the other, and that, when teaching of violence is denied, so is freedom of speech."

Not so, Jackson said, citing the Court's 1951 decision in Dennis v. United States, which upheld criminalization of membership in the Communist Party based on a "clear and present danger" exception to the First Amendment. The Court had recognized that exception in the 1919 case Schenck v. United States, which involved Socialist Party leaders who were prosecuted under the Espionage Act for distributing anti-draft literature during World War I. But the Court renounced the "clear and present danger" test in the 1969 case Brandenburg v. Ohio, which held that even advocacy of criminal conduct is constitutionally protected unless it is both "directed" at inciting "imminent lawless action" and "likely" to do so.

The Supreme Court's approval of deporting legal residents on ideological grounds, in other words, hinged on a view of the First Amendment that also tolerated criminally punishing U.S. citizens for their political affiliations. Needless to say, that is not how the courts (or most Americans) understand freedom of speech today.

The Trump administration's invocation of the "unconstitutionally vague" FPDP, FIRE notes, is apt to have a chilling effect on the speech of university students. In fact, that is Trump's explicit goal.

During his 2024 campaign, Trump said, "Any student that protests, I throw them out of the country. You know, there are a lot of foreign students. As soon as they hear that, they're going to behave." After Khalil's arrest, Rubio explained the message that the Trump administration is sending to students who engage in "anti-Semitic activities" on campus: "We're going to kick you out. It's as simple as that."

Jewish friends who oppose Khalil's detention insist he is not remotely antisemitic and favors a peaceful resolution of the Israeli-Palestinian conflict. But even speech that is explicitly antisemitic or pro-Hamas is constitutionally protected, and the power that Rubio is exercising sweeps much more broadly, encompassing any speech related to foreign policy that he views as contrary to the national interest.

"Allowing the Secretary of State to retaliate against speakers if he deems it in the national interest would place the United States among strange bedfellows when it comes to freedom of speech," FIRE says. It notes that the Chinese government asserts the authority to censor or punish speech that undermines "the interests of the state," while Russia's laws "permit the '[r]estriction of access to information' in the name of protecting 'morality,' its system of government, and the 'security of the state.'" Saudi Arabia likewise "prohibits expression that serves any 'foreign interest' conflicting with the 'national interest' or that 'stir[s] up discord among citizens.'"

The United States "has charted a different course than the world's censorial kings and regimes," FIRE says. "Secretary Rubio's attempt to deport Mr. Khalil violates the First Amendment and betrays more than two centuries of American commitment to free and open expression."