About a dozen protesters demonstrating in support of former Columbia University student Mahmoud Khalil were arrested on Tuesday as they clashed with New York City Police.

Immigration enforcement agents arrested Khalil, a permanent U.S. resident, in New York on Saturday, and he has been moved to an immigration detention center in Louisiana as the Trump administration seeks to revoke his legal status and deport him for his involvement last year in anti-Israel protests on campus.

U.S. District Judge Jesse Furman has ordered that Khalil, whose American wife is eight months pregnant, not be deported while the court considers the legal challenge brought by his lawyers, who argue the government is unlawfully retaliating against him for constitutionally protected speech. His lawyers want him brought back to New York and released under supervision.

On Tuesday, the NYPD made arrests after several protesters blocked a downtown street in Manhattan, even after warnings to clear the roadway, according to the New York Post.

NYPD officers clash with pro-Palestinian demonstrators as they gather outside Gracie Mansion to protest New York City Mayor Eric Adams holding Iftar and demand the release of Palestinian activist Mahmoud Khalil. New York City, U.S., March 11, 2025. (Getty Images)

Earlier, about 350 protesters marched from Washington Square Park to Federal Plaza Immigration Court as they chanted anti-Israel slogans and called for Khalil’s freedom, the outlet noted.

“There is only one solution, intifada revolution,” protesters chanted.

The group was attempting to make speeches in front of the federal courthouse in the middle of the street when they were told by the NYPD to continue walking. When demonstrators attempted to enter City Hall Park, police blocked them and forced them to turn around.

Protesters said Khalil was criminalized for expressing his freedom of speech. They also said he was a “political prisoner.”

“The Trump administration and the complicit Columbia University believe if they separate us from this key cornerstone of our community, our movement will begin to crumble,” the protesters shouted.

Officers also clashed with demonstrators outside Gracie Mansion to protest New York City Mayor Eric Adams holding Iftar — a meal Muslims have at sundown to break the daily fast during Ramadan — as they demanded Khalil’s release.

Pro-Palestinian demonstrators gather outside Gracie Mansion to protest New York City Mayor Eric Adams holding Iftar and demand the release of Palestinian activist Mahmoud Khalil. New York City, U.S., March 11, 2025. (Getty Images)

Free speech groups and other civil rights organizations have criticized Khalil’s detention as a violation of his First Amendment rights to freedom of expression, saying that the Trump administration is seeking to curb speech it disagrees with.

“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 Foundation for Individual Rights and Expression said in a statement.

President Donald Trump has vowed to root out alleged antisemitism by foreign citizens on college campuses after several anti-Israel protests at Columbia and other U.S. campuses after the Israel-Hamas war began on Oct. 7, 2023, following Hamas’ surprise attack on the Jewish State.

Khalil’s next court hearing is scheduled for Wednesday.