Over the past two weeks, immigration lawyers, scrambling from courthouse to courthouse, have secured provisional orders in five states stopping the Trump administration from using the Alien Enemies Act, an 18th-century wartime law, to deport Venezuelans accused of being gang members to a terrorism prison in El Salvador.
Judges have been harsh in appraising how the White House has used the powerful statute. “Cows have better treatment now under the law,” a federal judge in Manhattan said on Tuesday.
But at least so far, the one thing the lawyers have not managed to do is protect another — and harder to reach — group of Venezuelan migrants: about 140 men who are already in El Salvador, having been deported there under the act more than a month ago.
Early Friday, the American Civil Liberties Union took another shot at seeking due process for those men. Lawyers for the group filed an updated version of a lawsuit they brought against President Trump’s use of the Alien Enemies Act on March 15, the first that challenged his invocation of the law.
This time, the A.C.L.U. is asking a federal judge in Washington not to stop the men from being sent to El Salvador, but rather to help them return to U.S. soil.
When the A.C.L.U. filed its initial version of the suit, in Federal District Court in Washington, Judge James E. Boasberg issued an immediate order telling the administration to hold off sending any planes of Venezuelans to El Salvador under the Alien Enemies Act and to turn around any flights that were already in the air.
But that never happened. The administration’s inaction ultimately resulted in a threat by Judge Boasberg to begin a contempt investigation into whether Trump officials violated his original instructions — and now the updated lawsuit.
Altogether, the A.C.L.U. has filed at least seven lawsuits in seven federal courts across the country, challenging Mr. Trump’s proclamation on March 14 invoking the Alien Enemies Act as one of the central tools of his aggressive deportation agenda.
The suits have homed in on two different but related legal issues.
One is a significant procedural question: whether the Trump administration has provided migrants whom officials have asserted are subject to removal under the law with sufficient time and opportunity to challenge their deportations in court.
In a court filing unsealed on Thursday in an A.C.L.U. case in Texas, a top federal immigration official said that the administration had decided that “a reasonable amount of time” for migrants to express their desire to challenge deportations could be as little as 12 hours. The official said that migrants could have at least another day to file their challenges in court.
The other issue the A.C.L.U. has been exploring is more substantive: whether the White House should be allowed to use the act at all against the Venezuelan migrants. The act, which was passed in 1798, is supposed to be invoked only in times of declared war or military invasion against members of a hostile foreign nation.
Trump officials have repeatedly argued that the Venezuelans they are trying to deport are members of a criminal gang called Tren de Aragua and that their presence in the United States amounts to an invasion supported by the Venezuelan government. But that view has been rejected not only by some U.S. intelligence officials, but also by an increasing number of judges considering the A.C.L.U.’s lawsuits.
On Tuesday, for example, during a hearing in Federal District Court in Manhattan, Judge Alvin K. Hellerstein blasted Mr. Trump’s use of the statute, saying it was “contrary to law.”
Several times, Judge Hellerstein, who was appointed by President Bill Clinton, said he believed that Mr. Trump was using the law in inappropriate ways. He noted in particular that the law did not authorize the government “to hire a jail in a foreign country where people could be subjected to cruel and unusual punishment not allowable in the United States jails.”
When Tiberius Davis, a lawyer for the Justice Department took issue with that view, Judge Hellerstein shot him down.
“Your Honor, respectfully, once they’ve already been removed, they’re not in United States custody,” Mr. Davis said. “That’s El Salvador. They’re a separate foreign sovereign.”
“That’s exactly the point,” Judge Hellerstein said.
Another judge, Charlotte N. Sweeney, issued a ruling this week in Federal District Court in Denver determining that Mr. Trump’s proclamation had improperly stretched the meaning of terms like “war” and “invasion” in a way that ran counter to the actual text of the Alien Enemies Act.
“Because the act’s ‘text and history’ use these terms ‘to refer to military actions indicative of an actual or impending war’ — not ‘mass illegal migration’ or ‘criminal activities’ — the act cannot sustain the proclamation,” she wrote.
While the Supreme Court has not weighed in yet on the broad issue of whether the White House is using the statute properly, the court has made a decision on the procedural question of whether Trump officials have given migrants subject to the law due process.
Deciding they had not, the justices ruled in an order on April 7 that the Venezuelan migrants must be warned in advance if the government intends to deport them under the Alien Enemies Act so they can challenge them in court, but only in the places where they were being detained. The justices have not yet laid out their vision of how much — or what type of — warning the migrants should receive.
Still, the A.C.L.U. is using that ruling in its updated lawsuit filed in Washington in tandem with a second Supreme Court decision handed down in a different deportation case. In that decision, the justices determined that the White House had to “facilitate” the release of a Maryland man, Kilmar Armando Abrego Garcia, from Salvadoran custody after officials wrongfully deported him last month in violation of an earlier court order that expressly barred him from being sent to the country.
Lawyers for the A.C.L.U. have sought in essence to merge both of these rulings into a single tool to demand not only that the Trump administration provide the nearly 140 Venezuelans in Salvadoran custody with some way of challenging their circumstances, but also that officials take active steps toward securing their release, since they were not previously given the opportunity to do so.
The lawyers have argued, moreover, that it is appropriate to challenge the deportations in front of Judge Boasberg in Washington even though that is not where the men are currently being held. They say that Washington is the proper venue for legal actions when prisoners are in custody overseas.
But even if this strategy is successful, it could be difficult to force the administration to actually take steps to get the men released from Salvadoran custody.
Mr. Abrego Garcia, for example, remains in El Salvador two weeks after the Supreme Court ordered the White House to help secure his freedom.
Jonah E. Bromwich and Mattathias Schwartz contributed reporting.
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