Contempt of Court? Trump Administration Faces Legal Reckoning Over Deportation Flights

What Judge James Boasberg ordered — and how Trump is responding.

People protest alleged the movement of alleged Venezuelan criminals from the USA to a high-security prison in El Salvador.

Family members of Venezuelans who were moved from the USA to a high-security prison in El Salvador protest in Caracas, Venezuela, on April 9, 2025. (Getty Images)

President Trump is once again facing legal pushback over his hardline immigration policies.

On Wednesday, U.S. District Judge James Boasberg found there was probable cause to hold the Trump administration in criminal contempt for allegedly defying a court order to halt the deportation of migrants to El Salvador.

The confrontation dates back to March 15, when Trump invoked the centuries-old Alien Enemies Act to deport more than 130 Venezuelan nationals — many of them without due process — to a Salvadoran mega-prison. The move came just hours after Boasberg had ordered the administration to stand down, explicitly instructing officials to ground any deportation flights, or reroute those already in the air back to the United States.

But instead of compliance, Boasberg noted, top officials exhibited a “willful disregard” for the court’s order. In his ruling, the judge pointed to celebratory social media posts from administration figures, including Secretary of State Marco Rubio, who cheered the fact that deportation flights were still en route.

“The Constitution does not tolerate willful disobedience of judicial orders — especially by officials of a coordinate branch who have sworn an oath to uphold it,” Boasberg wrote in a 46-page opinion.

And the legal fallout may be just beginning: At least seven lawsuits have now been filed in federal courts across New York, Texas, Colorado, California, and Nevada by migrants facing imminent deportation under the Alien Enemies Act — setting up a broad and fast-unfolding legal test of the administration’s authority.

What did Judge James Boasberg say in his order?

Boasberg is giving the Trump administration one final chance to comply with his earlier directive: Advise him that they intend to take steps to “purge their contempt,” or identify the specific individuals who decided to continue the deportation flights despite his orders. If they don’t, the judge says he’s prepared to identify the officials responsible for defying his March 15 order and refer them for prosecution.

“The Court does not reach such conclusion lightly or hastily,” Boasberg wrote. “Indeed, it has given Defendants ample opportunity to rectify or explain their actions. None of their responses has been satisfactory.”

Boasberg didn’t just focus on the deportations themselves — he also took aim at how the administration responded in the lead-up to his ruling. He faulted officials for repeatedly dodging basic questions about the flights, a pattern that escalated into a dramatic turn: The Trump administration invoked the state secrets privilege, claiming it couldn’t reveal when the planes took off or landed, due to national security concerns.

The judge also criticized what he called “several hyper-technical legal arguments” aimed at justifying their actions — including the claim that they only had to follow his written order, not the oral one delivered from the bench. “Such arguments were unconvincing then and remain so now,” Boasberg wrote.

The order has drawn attention from legal experts, including Paul Schiff Berman, a law professor at George Washington University. “Judge Boasberg is not a radical by any means,” Berman says. “He’s served on the Foreign Intelligence Surveillance Court, where he regularly handled classified information. As he noted in his ruling, he doesn’t take this matter lightly, but it’s essential that the government comply with court orders. Therefore, he must investigate whether members of the administration intentionally defied his previous directive.”

What does Boasberg’s order mean, and how has Trump responded?

The order is a serious escalation in a high-stakes standoff between the judiciary and the executive branch. Though the Supreme Court has since lifted Boasberg’s pause on deportations, the judge is focused on the administration’s conduct while the order was still in effect — and whether officials knowingly violated it.

For the Trump administration, which has doubled down on its claim that it has no legal obligation to bring back any of the swiftly deported men, the ruling is a legal and political blow. Officials say that because the migrants are now in Salvadoran custody, the U.S. has no power to retrieve them, even though the administration paid El Salvador $6 million to detain them for the next year.

The White House responded in seeming defiance, signaling that this legal showdown is far from over: “We plan to seek immediate appellate relief,” said spokesperson Steven Cheung on X. “The President is 100% committed to ensuring that terrorists and criminal illegal migrants are no longer a threat to Americans and their communities.”

What does criminal contempt mean, and could Trump face jail time?

Probably not. Legal experts widely agree that Trump is unlikely to face imprisonment over the contempt proceedings. While criminal contempt — any offense in which someone is accused of disobeying a court order or disrupting proceedings — can carry fines or jail time, the Supreme Court’s 2024 ruling on presidential immunity casts a long shadow over any effort to prosecute a sitting or former president for actions tied to official duties.

“The president can’t be prosecuted for any criminal infringement related to his official presidential acts,” says Berman. “So assuming this qualifies as such, it would likely shield him from being held in criminal contempt.”

Legal experts suggest that lower-ranking officials may still face legal repercussions. And if contempt charges are brought against lower-ranking officials, Trump could simply pardon them.

“This is part of a broader showdown between the Trump administration and the judiciary,” Berman said. “The judge wants to get to the bottom of who was responsible — and hold them accountable.”