A federal judge conducting a “fact-finding” hearing Monday over the whether the Trump administration knowingly violated a court order when it handed over more than 200 alleged gang members to El Salvadoran authorities over the weekend told DOJ attorneys it was “heck of a stretch” for them to argue that his order could be disregarded.
U.S. District Judge James Boasberg, in verbal instructions issued during a hearing on Saturday, told the government to turn around any aircraft that had already departed the country if they were still in the air. However, sources said top lawyers and officials in the administration made the determination that since the flights were over international waters, Boasberg’s order did not apply, and the planes were not turned around.
The verbal instructions from Boasberg accompanied a temporary restraining order blocking the Trump administration from deporting noncitizens currently in custody, which the judge issued less than two hours after Trump attempted to invoke the 18th century Alien Enemies Act to deport alleged members of the Venezuelan gang Tren de Aragua.
Deputy Associate Attorney General Abhishek Kambli argued Monday during a “fact-finding” hearing convened by Judge Boasberg thay the judge’s directive on Saturday evening to turn around the flights did not take effect until it was put in writing later that evening.
“You knew in the morning that there would be a hearing at 5 p.m., so any plane that you put into an air in or around that time you knew that I was having a hearing about,” the judge responded. “So when I said directly to turn those planes around, the idea that my written order was pithier, that this could be disregarded, that’s a heck of a stretch.”
Lawyers with the Department of Justice refused to provide any additional information about the Trump administration’s recent deportations under the Alien Enemies Act, arguing disclosure of the information “national security and diplomatic concerns.”
Kambli insisted that the Trump administration had complied with the court’s written order — but provided no additional information to support the claim — before offering seemingly conflicting defenses and arguing the breadth of Trump’s authority as president made the removals lawful.
Alleged members of the Venezuelan criminal organization Tren de Aragua who were deported by the U.S. government, are detained at the Terrorism Confinement Center in Tecoluca, El Salvador in a photo obtained Mar. 16, 2025.
El Salvador Presidential Press Office via AP
“Once that they are in international waters, the president has authority outside of the Alien Enemies Act, which would not have been subject to either order,” Kambli said.
“My equitable powers are pretty clear that they do not lapse at the water’s edge,” Boasberg replied.
Kambli, however, repeatedly refused to provide more information to support his claims, insisting the information would risk national security.
“The information that I am authorized to provide is that no plane took off from the United States after the written order came through,” Kambli said.
Judge Boasberg — who previously oversaw the United States Alien Terrorist Removal Court — pushed back on the idea that the information could not be disclosed to the court.
“What’s the basis for not disclosing it to me?” he said.
“Your Honor, it is based on national security concerns with flight patterns and things of that sort,” Kambli said.
Boasberg ordered the DOJ to submit, by noon Tuesday, a sworn declaration of what they represented in a filing Monday — that a third flight that took off after his written order on Saturday carried detainees who were removable on grounds other than the Alien Enemies Act.
He said he would hold another hearing on Friday, barring any stay on the proceedings from the appeals court.
Prior to the hearing, DOJ attorneys argued in a Monday court filing that the court should vacate the hearing because they do not believe they violated the court’s orders, and they are not prepared to provide any further operational security or national security details to the plaintiffs or to the public.
Justice Department attorneys subsequently asked the circuit court to step in and stop the hearing and to assign the case to a different judge, but the hearing proceeded as planned.
Top DOJ leadership wrote in a filing that “an oral directive is not enforceable as an injunction” — claiming the government not violate any order because the oral directive in court, issued at 6:46 p.m. ET Saturday, was not in the written order that was filed to the docket at 7:25 p.m. ET.
In a court filing late Sunday night, lawyers with the ACLU and Democracy Forward Foundation argued that the Trump administration may have committed a “blatant violation” of the court’s directive by acting as if the order only applied to flights in U.S. airspace and individuals on American soil.
“This Court orally and unambiguously directed the government to turn around any planes carrying individuals being removed pursuant to the AEA Proclamation,” the filing said.
Lawyers with the Department of Justice insisted in a court filing Sunday that they removed “gang members” pursuant to Trump’s Alien Enemies Act proclamation before the court issued its order.
However, lawyers representing some of the migrants argued that assertion not only conflicts with the timeline of events but also misconstrues when the United States loses jurisdiction of the noncitizens.
“Whether or not the planes had cleared U.S. territory, the U.S. retained custody at least until the planes landed and the individuals were turned over to foreign governments,” the plaintiffs’ filing said. “And the Court could not have been clearer that it was concerned with losing jurisdiction and authority to order the individuals returned if they were handed over to foreign governments, not with whether the planes had cleared U.S. territory or had even landed in another country.”
Plaintiffs’ attorneys said that based on publicly available information, it appears that two flights carrying migrants under the Alien Enemies Act landed after the court’s verbal and written orders. They added that “public comments made by Defendants and the President of El Salvador” boasting about the court being “too late” to stop the deportations reinforces concerns that the Trump administration may have violated the order.
“Defendants could have turned the plane around without handing over individuals subject to the Proclamation and this Court’s [Temporary Restraining Order],” the lawyers argued.
Finding the deportations would cause irreparable harm, Boasberg’s temporary restraining order on Saturday barred the Trump administration from deporting “all non-citizens who are subject to the AEA proclamation” for at least 14 days.
“You shall inform your clients of this immediately any plane containing these folks that is going to take off or is in the air needs to be returned to the United States,” Boasberg said during Saturday’s hearing. “However that’s accomplished, turning around the plane, or not embarking anyone on the plane. … This is something that you need to make sure is complied with immediately.”
