SF Immigration Attorney Says First Amendment Should Protect Mahmoud Khalil From Deportation

File folders and a laptop were spread across the dining room table in Marc Van Der Hout’s home in San Francisco’s Noe Valley neighborhood. The veteran immigration lawyer was working overtime to represent Mahmoud Khalil, one of the pro-Palestinian student activists the Trump administration has been trying to deport.

Khalil’s story has sparked national attention, but it’s not totally uncharted legal territory for Van Der Hout, 76. He has been fighting for the civil rights of immigrants for decades. This time, that means working on two cases at once.

First, Van Der Hout and a law partner are fighting Khalil’s deportation before an immigration judge at the detention facility in Jena, La., where Khalil has been held for over two months.

Second, Van Der Hout is part of a national team of lawyers, including the ACLU and the Center for Constitutional Rights, arguing in federal district court in New Jersey that the Trump administration’s push to deport Khalil is illegal.

“You cannot deport someone under the laws for their beliefs,” Van Der Hout said. “That’s against the Constitution. But that’s what the government’s trying to do in this case and in other similar cases.”

Khalil, 30, was finishing his master’s degree at Columbia University’s School of International and Public Affairs when he was arrested March 8 in the lobby of his student apartment building by U.S. Immigration and Customs Enforcement agents. Administration officials later indicated that the arrest stemmed from his role in campus protests of Israel’s bombardment of Gaza, following Hamas’ attack on Israel in October 2023. Khalil, a Syrian-born Palestinian, has not been charged with a crime.

Khalil is among numerous immigrant students and academics who’ve been targeted by the Trump administration, especially after speaking out about the war in Gaza. But in recent days, judges have ordered ICE to release several of them from detention, including Columbia student Mohsen Mahdawi, Tufts University student Rumeysa Ozturk and Georgetown University scholar Badar Khan Suri.

Echoes of the Cold War

Khalil’s case centers on an obscure 1952 provision in immigration law that allows the Secretary of State to personally declare someone deportable if their presence or activities could have “serious adverse foreign policy consequences” —even if, like Khalil, they’re a lawful permanent resident (or green card holder), the most durable legal status a noncitizen can have.

Congress modified the Cold War-era law in 1990 to protect speech and associations that were otherwise lawful, and raised the standard for deportation. At that time, lawmakers said that the foreign policy deportation power should be used “sparingly” and “not merely because there is a likelihood that an alien will make critical remarks about the United States or its policies.”

“It has been rarely, rarely used,” Van Der Hout said. “It is completely outrageous that they are using this type of statute to go after Mahmoud in this case.”

Over the years, Van Der Hout has litigated a number of nationally significant cases — and he said Khalil’s case echoes one from nearly four decades ago. In that case, which went all the way to the U.S. Supreme Court, the attorney represented a group of pro-Palestinian activists in Los Angeles, dubbed the LA-8, who the Reagan administration was trying to deport.

“They basically used the same facts: ‘You’re speaking out against U.S. policy in the Middle East, speaking out in support of Palestinian groups overseas,’” he said. “We eventually won that case, but it took 20 years.”

Fast forward to today, and a similar argument is playing out.

Shortly after Khalil’s arrest, Secretary of State Marco Rubio appeared on CBS’ “Face the Nation” saying the government had the right to deport student visa holders, as well as green-card holders like Khalil, for their protest activity.

“We don’t need these people in our country. We never should have allowed them in in the first place,” he said. “If you are in this country to promote Hamas, to promote terrorist organizations, to participate in vandalism, to participate in acts of rebellion and riots on campus, we never would have let you in if we had known that.”

In a memo to the Department of Homeland Security, Rubio cited the rarely-used 1990 immigration statute and declared that Khalil was deportable because his presence in the U.S. would “compromise a compelling foreign policy interest” as a result of his participation in “antisemitic protests and disruptive activities, which fosters a hostile environment for Jewish students in the United States.”

The memo was the only evidence the government submitted to the Louisiana immigration judge Jamee Comans in pressing for Khalil to be deported. And the judge did not allow Khalil’s legal team to present evidence in his defense at an April 10 hearing, Van Der Hout said. Instead, Comans swiftly ruled in the government’s favor, saying she had no authority to question Rubio’s determination. Comans’ ruling is not yet final, and she has set a second hearing in the immigration case for May 22.

Van Der Hout said the government’s logic is unfounded.

“Really, what they’re saying is, if you criticize Israel, you’re antisemitic. And that’s basically what this case is about,” he said. “I’m Jewish, and I’ve criticized Israel many times for what it’s done to the Palestinian people, and that is not antisemitic.”

He added that Khalil has worked with Jewish groups and spoken out against antisemitism on Columbia’s campus. As evidence, several Jewish Columbia students submitted letters to the court testifying that they consider Khalil an ally, not an antagonist.

A First Amendment Battle With Trump

What the case against Khalil is really about is free speech, Van Der Hout said.

“I think it’s very frightening, and the American public should be very, very concerned that this administration is trying to restrict free speech — no matter whose it is,” he said. “Everybody in the United States, no matter what their status… is protected by the First Amendment of the Constitution. That is absolutely clear.”

But President Trump’s border czar, Tom Homan, has called Khalil a “national security threat” and suggested the First Amendment does not protect his actions.

“Can you stand at a movie theater and yell ‘Fire?’ Can you slander someone verbally? Free speech has limitations,” he said in the days after Khalil’s arrest.

Khalil’s free speech argument is central to the case before U.S. District Judge Michael Farbiarz in New Jersey. Farbiarz, a Biden appointee, is considering a habeas corpus petition charging that Khalil’s arrest and detention are unconstitutional violations of his rights and that the government is retaliating against him for his political views.

Though similar issues arose in the LA-8 case and a couple of others over the years, they were ultimately decided on other grounds, and the question of whether a green card holder can be deported for First Amendment-protected activity hasn’t been squarely settled, UCLA Law Professor Hiroshi Motomura said.

“In a lot of the Trump administration immigration initiatives, they’re pushing things further than other administrations, and so you have issues that haven’t been in the courts before,” he said.

In addition to the free speech concerns, Motomura described the case against Khalil as part of a sea change in the country’s approach to immigration. He said the Trump administration is trying to redefine immigrants as “invaders,” undermining American society, in order to expel them. And it’s sowing doubt among green card holders about how permanent their legal status really is.

“The Trump Administration is saying to these folks, ‘Oh, you thought you were on the inside. You thought you were just about American. But guess what? You’re not.’” Motomura said. “What the administration is trying to do is a really radical intervention in all notions of who belongs and who doesn’t and how we think about this country. And that’s why it’s so fundamental.”

Fielding emails and calls from his dining room table, Van Der Hout continued assembling evidence and editing legal briefs. He believes the outcome of Khalil’s case could have broader implications for Americans, as a test run for quashing dissent among those who speak out against the Trump administration.

“It is very frightening because, yes, it’s right now being directed at immigrants, but it could be directed at United States citizens very soon,” he said.

Late last month, Judge Farbiarz ruled that Khalil’s case can move forward. In it, Khalil is not only challenging his own detention and Rubio’s determination that he’s deportable, but asking the judge to find that the Trump administration’s policy of seeking to deport any noncitizen for “protected speech” is unconstitutional, Van Der Hout explained.

For now, they wait. Farbiarz could rule any day —on the case as a whole or simply the question of whether Khalil can go home to New York while the legal fight unfolds. Last month, while he was incarcerated, Khalil’s wife gave birth to their first child. From the detention center, Khalil published an open letter to his newborn son on Mother’s Day, saying he was “not absent out of apathy, but out of conviction.”

“I probably speak to him every other day,” Van Der Hout said. “He is calm. He understands it’s a political fight. He understands he’s being made an example of.”