A Tale of Two Deportation Cases

Attorney General Pam Bondi at the Justice Department in Washington, D.C., February 12, 2025. Inset: Mahmoud Khalil at Columbia University, left, and Salvadoran police officers escort alleged members of the Venezuelan gang at the El Salvador International Airport in San Luis Talpa, El Salvador, March 16, 2025. (Craig Hudson, Jeenah Moon/Reuters, Secretaria de Prensa de la Presidencia/Handout via Reuters)

In the case of the Venezuelans, the DOJ is resisting the kind of meticulous review that it provided in Mahmoud Khalil’s case.

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In the case of the Venezuelans, the DOJ is resisting the kind of meticulous review that it provided in Mahmoud Khalil’s case.

W hat a remarkable contrast between the Trump Justice Department’s stances in the two big alien deportation cases in which there were major developments on Wednesday.

With respect to Mahmoud Khalil, the Justice Department took the position that it was essential for the court to understand minute-by-minute where the alien in question was. After all, the answer to the question of whether the Manhattan federal judge had jurisdiction over the alien hinged on this inquiry.

Federal court in Manhattan — the Southern District of New York (SDNY) — has never been a home game for President Trump. Perhaps understandably, the administration would rather litigate the controversial Khalil case someplace else. Its preference was Louisiana, where the federal district judges and, eventually, the Fifth Circuit appeals court, a conservative-leaning tribunal, would likely be more hospitable to the president’s claims of sweeping executive power (which, in this instance, I believe are well-founded).


Hence, the Trump DOJ encouraged SDNY Judge Jesse Furman to establish precisely where Khalil was in the wee hours of a Sunday morning — at the moment when his attorney filed an emergency petition on his behalf. As our David Zimmermann has reported, Judge Furman did precisely that and correctly concluded that he could not exercise jurisdiction.

DOJ was remarkably expansive in recounting Khalil’s travels and the judgment calls the government made along the way. After being arrested and processed in the SDNY, Khalil was detained overnight in a New Jersey detention facility. He was physically in that state (the district of New Jersey for purposes of federal venue) when his habeas corpus petition was filed shortly after 4 a.m. Sunday morning. It was only later in the day, the DOJ explained, that federal agents transported him from New Jersey to JFK International Airport in Queens (which is in the Eastern District of New York, although the Khalil would almost surely have had to pass through the SDNY to get there from New Jersey) for a flight to Dallas (the Northern District of Texas) and finally another flight to the airport and detention facility in the Western District of Louisiana.




Candor and this exacting description of the journey helped the DOJ’s litigating position. To be sure, the administration did not get everything it wanted. Its top-line request was that Furman dismiss the case, which he declined to do given the significant questions it raises about free speech, free association, and the government’s authority to deport aliens legally residing in the U.S. Those substantive issues will be left to the next judge to decide.


Furman, moreover, declined the government’s request that he transfer the case to Louisiana. While that’s where the immigration agents took Khalil, it’s not where he was when his petition was filed. With the government having established that Khalil was in New Jersey at that point, that’s where Furman transferred the case for further proceedings. By law, a habeas petition in this situation should be directed to the federal custodian of a detainee in the place where he is physically located.

To the Trump DOJ, however, this seems like a better draw than the SDNY. We should also note that Judge Furman rejected Khalil’s claim that the Trump administration had engaged in deceptive conduct. He accepted that Khalil was transferred to New Jersey, as detainees frequently are, because of a lack of immigration-enforcement detention space in New York. Yes, Khalil was moved forthwith to Louisiana (where his deportation hearing is scheduled for March 27), but that was because of a bedbug problem at the Elizabeth Detention Center in Newark, N.J., which has limited the government’s use of that facility for anything but short-term detention.


Khalil was not singled out along the way. He made his voyage with other immigration detainees who were similarly shuffled from place to place. His lawyer ended up filing the petition in the SDNY because that’s where she was led to believe Khalil was at 4 a.m. Sunday morning, March 9. But counsel was not intentionally deceived by the government; rather, the online locater for detainees was not updated until later Sunday morning, at which point the attorney was accurately informed that Khalil was in New Jersey but about to be flown south.

That is to say, the fact that Judge Furman is an Obama appointee did not mean he assumed bad faith on the part of the government. He asked pointed questions, as judges weighing tough questions are supposed to do. The Justice Department, as it is supposed to do, ensured that the court was given accurate information (as Khalil’s lawyer conceded). Armed with that information, the judge made the correct legal ruling, which, of course, was the point.


Things are very different in the Washington, D.C., case involving hundreds of Venezuelan aliens the Trump administration deported on Saturday, evading judicial review of its dubious claim that the Alien Enemy Act (along with what the DOJ vaguely claims is President Trump’s constitutional authority) authorized the president to deport the aliens in the absence of any judicial process.

In the case of the Venezuelans, the Trump DOJ is fighting tooth and nail against the kind of meticulous minute-by-minute review of how the aliens were handled that it provided in Khalil’s case. It is refusing, in fact, to answer rudimentary questions pressed by Chief Judge James Boasberg of the Washington, D.C., district court about where the alien petitioners were at the relevant times — plainly because the administration and the DOJ did not comply with an order that the aliens not be deported, and hope to obscure that, fully aware of the judge’s order, they could easily have returned the alien detainees to the United States but instead chose to hand them over to a foreign government for what they hoped would be detention outside U.S. court jurisdiction (just as the Bush-43 administration hoped that detaining captured jihadists at a naval base in Guantanamo Bay, Cuba, would put them beyond the writ of federal judges — a bad bet, it turned out).


The judge has directed the Trump DOJ to inform him under oath — ex parte and under seal if necessary — exactly what time and from where the planes took off in the United States, what time they left U.S. airspace, and what time they landed in which countries.




In what would be hilarious if it weren’t behavior so out of character for the DOJ, two hours before their noon deadline on Wednesday, prosecutors filed yet another request to delay answering the judge’s questions (until noon Thursday) and, for lawyers who were asking a judge’s indulgence, their tone was bracingly petulant. The submission, reportedly signed by Attorney General Pamela Bondi and Deputy Attorney General Todd Blanche, among others, accused the judge of “devolv[ing] [the case] into a picayune dispute over the micromanagement of immaterial factfinding.”

Imagine if you were the subject of a DOJ investigation and had misled investigators. If they demanded clarification while considering whether to charge you for false statements, do you suppose they’d just drop the whole thing if you lectured them about not letting the matter “devolve into a picayune dispute over the micromanagement of immaterial factfinding?”


I doubt it.

It’s hard to say what’s more risible: Main Justice’s rant about how Boasberg is interfering with “the President’s authority to protect the national security and manage the foreign relations of the United States” or its threat to withhold responses to Boasberg’s questions under the “state secrets” doctrine.

State secrets? The flight data information in question is a matter of public record — the New York Times has already published the minute-by-minute details. And back in February, as one of his first official acts running Trump’s foreign relations, Secretary of State Marco Rubio announced with great fanfare the agreement of El Salvador “to accept and incarcerate deportees from the U.S. of any nationality, including criminals with American citizenship currently imprisoned in the U.S.,” as CBS News put it. This is such a big secret that, even as the DOJ was signaling the state secrets claim, Secretary Rubio was on Hugh Hewitt’s radio show, relating in lush detail how he made the agreement with the Salvadoran president and what each side hopes to gain from it. It is an arrangement that Salvadoran President Nayib Bukele very publicly confirmed on social media, explaining that transferees from America would be held in a two-year-old “mega-prison” his regime had constructed in its crackdown on criminal gangs.

So not a state secret is what happened to the Venezuelan detainees that Bukele — whose relishing of social media is reminiscent of another president whose name escapes me — mocked Boasberg’s order in a post after the Venezuelans were led into the mega-prison: “Oopsie . . . Too late.”


Boasberg is not trying to micromanage foreign policy. The court is not questioning the legality or prudence of our government’s arrangements with other countries to detain prisoners. Conditions of confinement could become an issue at some point if someone with standing makes a claim that the U.S. is responsible for a foreign country’s sub-standard detention standards. But that is not Boasberg’s concern. Remember, Boasberg, though an Obama appointee to the district court, was originally put on the bench in Washington, D.C., by President George W. Bush. Chief Justice John Roberts put him on the Foreign Intelligence Surveillance Court (FISC), where he ultimately became chief judge. This is not a “Radical Left Lunatic of a Judge, a troublemaker and agitator.” This is not a judge who, like Judge Amir Ali, has tried to micromanage U.S. policy regarding foreign aid (for which we derided Judge Ali here at NR). On the FISC, Boasberg signed off on numerous top-secret intelligence programs; he is uniquely aware that the government has to do business with all kinds of shady characters in the pursuit of American interests around the world. He is not questioning the president’s political judgment.

The relevant questions are (a) whether the Venezuelan detainees were entitled to judicial review before the administration deported them, (b) whether the administration operated in stealth because it realized its legal justification was tenuous (rather than because national security somehow required stealth . . . about a detention arrangement the administration can’t stop talking about publicly), and (c) whether prosecutors misled and defied the court — under circumstances in which, if the government believed Boasberg’s inquiries or order were lawless, it could have filed an emergency appeal. Or it could have forthrightly informed Boasberg that the flights had departed and that the administration believed the court lacked jurisdiction to direct that they be turned around.


What Boasberg is doing has nothing to do with foreign policy or state secrets. He is doing what any federal judge would do if there were a colorable reason to believe the Justice Department was not candid with the court.

Unlike in the Khalil case, the Trump DOJ is resisting the court’s request for a minute-by-minute account of how the Venezuelan alien detainees were moved from place to place. What’s at stake is not secret information. It’s embarrassing information.

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