Just a week after immigration officials arrested and detained anti-Israel student activist at Columbia University, Mahmoud Khalil, more than a dozen lawyers have lined up to help the 31-year-old activist challenge his impending deportation. 

However, members of Mr. Khalil’s so-called legal dream team are raising eyebrows for their controversial client lists and their anti-Israel activism. 

One such attorney, Ramzi Kassem, who was present during Mr. Khalil’s Wednesday hearing, built his career as the go-to legal counselor for al Qaeda terrorists stuck in Guantanamo Bay. One of his clients, al Qaeda member Ahmed al-Darbi, pleaded guilty in 2014 for planning a deadly terrorist attack on a French oil tanker off the coast of Yemen. He has represented at least 14 other Guantanamo Bay detainees. 

Mr. Kassem, also a Columbia graduate, was a prominent anti-Israel activist on campus. He took up the cause of petitioning the school to rename a dining hall sandwich known as the “Israeli wrap” to what he called the “more inclusive” Middle-Eastern wrap. In columns for the university paper, Mr. Kassem bragged about throwing stones at Israel from the Lebanese border. 

Mr. Kassem has also been vocal in his criticism of the “terrorist” label and in a 2001 op-ed described the September 11 attacks as a result of “resentment these terrorists felt towards the United States” as well as “our country’s policies.” Two decades later, he went on to join the Biden administration as a Senior Policy Advisor for Immigration at the White House Domestic Policy Council. He has not yet responded to the Sun’s request for comment. 

Mr. Khalil will also receive legal support from Diala Shamas, an attorney at the Center for Constitutional Rights. Ms. Shamas has a long history of anti-Israel activism and first responded to the October 7 massacare by resharing a post on X that claimed that Israel was crafting a “preemptive excuse for genocide” by calling the massacre “Israel’s 9/11.” It only took 9 days into the war before Ms. Shamas declared that Israel was committing a “genocide.” 

Ms. Shamas made headlines in 2024 for participating at a controversial lecture at SUNY Downstate Medical Center in Brooklyn that accused Israelis of committing health care “genocide” in Gaza. The panel was denounced by the Jewish American Medical Association as “medical propaganda.” She has not yet responded to the Sun’s request for comment.

Mr. Kassem and Ms. Shamas represent just a fraction of Mr. Khalil’s 19-person legal team which maintains that Mr. Khalil’s arrest is an assault on pro-Palestine speech. His case has also been taken up by the American Civil Liberties Union and the New York Civil Liberties Union. An online fundraiser for Mr. Khalil’s legal defense, “family support” and “long-term justice efforts” has already raised $369,000, nearing its goal of $500,000. 

The 31-year-old activist was arrested last weekend by Immigration and Customs Enforcement officers on a State Department order to revoke his visa and green card. His deportation, however, was temporarily halted by U.S. District Judge Jesse Furman who ruled that Mr. Khalil must remain in the country as the courts weigh his case. Judge Furman refrained from ruling on the petition by Mr. Khalid’s lawyers for his illegal arrest. 

Mr. Khalil, a 31-year-old graduate student born in Syria, served as one of the leading organizers for the anti-Israel student group at Columbia University that was behind some of the most violent protests in the country. He was recently spotted participating in the Barnard College protests that saw anti-Israel student activists illegally occupy a college library and hand out propaganda pamphlets written by the “Hamas Media Office.” 

A spokeswoman for the Department of Homeland Security, Tricia McLaughlin, confirmed in a statement over the weekend that Mr. Khalil’s arrest was related to allegations that he “led activities aligned to Hamas, a designated terrorist organization.” On Tuesday, the White House added that he allegedly distributed pro-Hamas propaganda fliers. 

Mr. Khalil is the first non-citizen student to face deportation for pro-terror activism as the Trump administration follows through on its aggressive approach to quashing campus antisemitism. President Trump has pledged that Mr. Khalil won’t be the last. 

His arrest has sparked debate over the First Amendment and the rights of visa or green card holders. Scores of protestors showed up to his Wednesday hearing in downtown Manhattan, including left-wing actress Susan Sarandon who came under fire last year for claiming that Jews, post October 7, are “getting a taste of what it feels like to be a Muslim in this country.”

On Thursday, hundreds of activists stormed the lobby of Trump Tower in Manhattan to call for Mr. Khalil’s immediate release. The demonstrators, who were united by anti-Israel group Jewish Voice for Peace, carried banners that read: “Jews say Free Mahmoud & Free Palestine” and “Fight Nazis Not Students.” At least 98 individuals were arrested. 

Mr. Khalil is currently being held at an ICE detention center in Louisiana. Attorneys for the Department of Justice are pushing for his legal proceedings to take place in New Jersey, where Mr. Khalil was initially taken after his arrest, or Louisiana.