Decoding the White House’s Conflicting Messages on Deportation Flights

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The White House is attempting a balancing act regarding its swift deportation of hundreds of immigrants to El Salvador, a situation unlikely to resolve smoothly, possibly intentionally.

During Monday’s White House briefing, Press Secretary Karoline Leavitt faced the difficult task of asserting the administration’s compliance with a judge’s orders while simultaneously claiming those same orders were non-binding. This occurred while also defending a senior White House aide’s televised statement, “I don’t care what the judges think,” in response to questions about those orders.

The shifting rhetoric was unified by a flexible approach to facts and justifications.

This strange situation began late Friday when President Donald Trump invoked wartime authority to initiate mass deportations. According to the White House, 137 individuals, identified as gang members from Venezuela, were deported to El Salvador. There, they were met by military, law enforcement, and videographers, before being sent to a location of concern to human rights advocates. An additional 124 individuals were also transported to San Salvador’s airport under different federal laws.

On Saturday, after news of the plan was leaked, U.S. District Judge James Boasberg attempted to halt the deportations without hearings and instructed the administration to return planes carrying 261 migrants. However, the planes had already left U.S. airspace, placing them, according to the administration’s view, beyond the reach of U.S. courts.

By Sunday, Trump’s allies predictably defended the unchecked executive powers and criticized the judges’ authority. Meanwhile, Secretary of State Marco Rubio endorsed a social media post from Salvadoran President Nayib Bukele, expressing schadenfreude at the court’s intervention with a simple, “Oopsie… Too late.”

Trump’s legal team is citing a 1798 law to justify deporting the migrants without court appearances, though the law hasn’t been used since World War II. Legal experts debate its applicability, but Trump’s associates seem more interested in offering various explanations to see which gains the most support, rather than focusing solely on the legal arguments.

During Monday’s press briefing, Leavitt appeared to present multiple justifications, each potentially valid, but collectively creating an impression of a desperate search for justification.

“This administration acted within the confines of the law,” Leavitt stated, omitting that Judge Boasberg, the legal arbiter, had ordered the migrants to remain in the United States.

“All of the planes subject to the written order of this judge departed U.S. soil,” Leavitt noted, implying that international flights were beyond the judge’s jurisdiction. She did not mention that this argument might be invalid and that the judge had intended to ground the planes.

“There’s actually questions about whether a verbal order carries the same weight … as a written order, and our lawyers are determined to ask and answer those questions in court,” Leavitt said, failing to acknowledge that ignoring a judge rarely benefits lawyers.

The timeline illustrates the rapidly changing situation.

At 5 p.m. on Saturday, Boasberg inquired about the start time of the deportations, leading to a court recess for government lawyers to investigate. The plane departed at 5:45 p.m. At 6:52 p.m., Boasberg ordered the planes back to U.S. runways, according to a detailed timeline. The migrants landed at 8:02 p.m.

Throughout the weekend, Trump’s aides and allies openly celebrated outmaneuvering the judge, with even the top border policy official boasting about the administration’s ability to bypass the courts.

“We’re not stopping,” border czar Tom Homan told Fox News. “I don’t care what the judges think. I don’t care what the left thinks. We’re coming.”

This situation has sparked debate in Washington about whether the Trump administration intentionally initiated the deportations on Friday evening to provoke a court battle that could ultimately expand the executive branch’s power over immigration policy.

This approach—acting too quickly for the courts to effectively respond and relying on legal representatives and allies to create confusion—may become a recurring strategy of this White House.

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