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A federal judge Monday ordered the U.S. Justice Department to provide a sworn declaration by noon ET Tuesday with details on how planeloads of alleged members of Tren de Aragua were deported 

despite his order to turn the planes around

The hearing on Monday centered on whether the government complied with Judge James Boasberg's temporary restraining order, and it included a debate about when exactly the order was issued and where U.S. custody over deportees ends. Also discussed: whether an oral order versus a written order holds the same weight when it comes to restraining 

It came after Boasberg's emergency order Saturday that told the administration to stop using wartime powers to immediately deport people it said were part of the Tren de Aragua gang, and turn around any planes already in the air. Senior Justice Department officials in a filing on Sunday argued that the order came too late to stop the deportations, as planes were already outside U.S. territory.

The American Civil Liberties Union and Democracy Forward had sought to block the deportations of five Venezuelan men for 14 days and later broadened the request to all people who could be deported under Trump's Alien Enemies Act proclamation concerning Tren de Aragua.

Government lawyers on Sunday wrote that "some gang members subject to removal under the Proclamation had already been removed from United States territory" by the time the judge issued his written order at 7:26 p.m. ET on Saturday.

But lawyers from the civil rights groups argued that even though the judge's written order came at 7:26 p.m., the judge had actually issued an oral order between 6:45 p.m. ET and 6:48 p.m. ET that directed the government to turn around any planes carrying people being removed under the Alien Enemies Act. And that oral order should hold the same weight, they said.

The groups quote the judge as saying "that you shall inform your clients of this immediately, and that any plane containing these folks that is going to take off or is in the air needs to be returned to the United States. … However that's accomplished, whether turning around a plane or not embarking anyone on the plane or those people covered by this on the plane, I leave to you. But this is something that you need to make sure is complied with immediately."

"Plaintiffs remain extremely concerned that, regardless of which time is used, the government may have violated the Court's command," the groups wrote in a filing on Monday. They said that the U.S. government retained custody of people until the planes landed and they were turned over to El Salvador — and that it didn't matter whether the plane was over international waters or not.

On Monday, White House press secretary Karoline Leavitt said there were "questions about whether a verbal order carries the same weight as a legal order as a written order, and our lawyers are determined to ask and answer those questions in court."

The plaintiffs cited FlightAware data that showed two planes carrying the deportees were still in the air by the time of the judge's written order at 7:26 p.m. A third plane took off at 7:37 p.m., after the written order was released, they said.

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At issue was whether planeloads of alleged members of the Tren de Aragua gang were deported despite the judge's order to turn the planes around.

Judge seeks sworn declaration from Justice Department in deportation case

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