Judge Questions Trump’s Deportation of Venezuelans, Setting Up Legal Showdown

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A U.S. judge on Monday ordered Trump administration officials to clarify whether they violated his ruling by deporting hundreds of alleged Venezuelan gang members over the weekend. The move sets up a potential constitutional clash between the presidency and the judiciary. 

The White House, asserting broad executive power, maintains that federal courts “have no jurisdiction” over President Donald Trump’s authority to expel foreign enemies under the Alien Enemies Act, an 18th-century law rarely invoked outside wartime. 

Judge James Boasberg, presiding in Washington, scheduled a hearing for 5 p.m. ET (2000 GMT) on Monday and instructed the government to provide specific details about whether the deportation flights to El Salvador departed before or after his order. 

The hearing follows an emergency filing by the American Civil Liberties Union (ACLU) and other advocacy groups demanding clarity on the administration’s actions. 

This development escalates Trump’s ongoing challenge to the constitutional system of checks and balances, as well as the judiciary’s role in curbing executive power. 

During an emergency hearing on Saturday, Boasberg issued a two-week injunction blocking Trump’s use of the Alien Enemies Act to deport 238 alleged members of the Venezuelan gang Tren de Aragua. He instructed that any flights already en route should return to the U.S. His written order, according to the Justice Department, appeared in the court’s docket at 7:26 p.m. ET (2326 GMT). 

However, on Sunday, El Salvador’s President Nayib Bukele posted footage on social media platform X, showing detainees being removed from a plane under the cover of darkness. 

“Oopsie … too late,” Bukele wrote in response to reports of Boasberg’s ruling. 

White House Press Secretary Karoline Leavitt denied any violation of Boasberg’s order while simultaneously questioning its legitimacy. 

“A single judge in a single city cannot direct the movements of an aircraft … full of foreign alien terrorists who were physically expelled from U.S. soil,” Leavitt stated. 

The administration’s actions reflect an increasing willingness to defy judicial oversight. Since taking office, Trump has tested the limits of executive power by challenging congressional spending authority, dismantling federal agencies, and firing tens of thousands of government workers. 

On Monday, Trump’s border czar, Tom Homan, dismissed concerns over the court ruling and made it clear deportations would continue. 

“Once you’re outside the border, you know, it is what it is. But they’re in international waters, already on the way south, close to landing. You know what? … We did what we had to do,” Homan said during a Fox News appearance. 

When asked about future deportation flights, Homan was blunt: 

“Another flight, another flight every day. We’re not stopping. I don’t care what the judges think,” he added. 

With a Republican-controlled Congress backing his agenda, Trump’s administration has faced legal resistance primarily from federal judges. Advocacy groups have raised concerns that the administration is now openly disregarding court rulings, testing the resilience of judicial oversight in the face of expanding executive authority.

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