Former federal judge says Trump is playing a 'dangerous game' with Judge Boasberg

Washington (CNN) — US District Judge James Boasberg said Thursday that he is looking at whether “probable cause” exists to hold Trump administration officials in contempt for violating his orders halting the use of the Alien Enemies Act to deport alleged Venezuelan gang members.

The comments from Boasberg mark a significant escalation in a standoff between the administration and the chief judge of the trial-level court in Washington, DC, over deportation flights it allowed to continue last month despite his orders that the government turn the planes around immediately pending a legal challenge to Trump’s use of the sweeping wartime authority.

The case has emerged as one of the highest-profile and most contentious court battles of President Donald Trump’s second term, with the president calling for Boasberg’s impeachment over his handling of the matter, leading to a rare rebuke of the rhetoric from Chief Justice John Roberts.

Boasberg signaled repeatedly during a hearing Thursday afternoon that he was inclined to move forward with contempt proceedings, including, potentially, with witness testimony from government officials – though the judge added that he won’t make a decision on whether to do so until next week at the earliest. At the start of the hearing, he told Justice Department attorney Drew Ensign that there was a “fair likelihood” that the government didn’t comply with his orders but that he was open to be persuaded otherwise.

Thursday’s hearing lasted less than an hour, but much of it featured tense exchanges between Boasberg and Drew Ensign, a Justice Department attorney whose answers to the judge’s questions about the government’s actions last month seemed to irk the court.

Ensign at times stonewalled Boasberg, claiming that he couldn’t answer some of the judge’s questions because the information sought was covered by attorney-client-privilege. And the lawyer appeared exasperated as he ticked through the individuals within the Trump administration whom he quickly told about the judge’s orders on March 15.

But his non-answer on certain questions central to the defiance issue drew some of the most notable responses from the judge.

“You standing here have no idea who made the decision to not to bring the planes back or have the passengers not be disembarked upon arrival?” Boasberg asked at one point after Ensign said he didn’t know who made those calls.

”As we proceed with potential contempt proceedings, that may become relevant,” the judge added.

Throughout the hearing, the judge appeared visibly frustrated with Ensign. He threw his glasses onto the table in front of him in frustration as he questioned the attorney, who stuttered through some of his responses, declaring that he had no knowledge of the operational details of the flights headed to El Salvador.

The judge’s questions revealed his belief that the government rushed to deport migrants under the Alien Enemies Act proclamation to get ahead of a potential court order that would block the administration from doing so.

Noting that, even before Trump’s proclamation was released, government officials were organizing flights that would ultimately remove the migrants under the authority, Boasberg said the “only inference” was that preparations were being made to quickly deport people under the 1798 law once it was announced. Once the proclamation was released, prompting an overnight challenge from the ACLU, the government continued to move forward with deportation plans, Boasberg pointed out.

“Why wouldn’t the prudent thing be to say, ‘Let’s slow down here. let’s see what the judge says?’” Boasberg asked.

The tension in the courtroom was palpable – onlookers never took their eyes off the judge as he pressed Ensign on whether he truly did not know that people were still being put on the planes carrying deportees on March 15, including Kilmar Armando Abrego-Garcia, whom the Trump administration has admitted was sent to El Salvador due to an “administrative error.”

Lawyers from the Justice Department looked visibly concerned during the proceedings, with one placing his hand on his forehead and looking down as the questioning intensified.

At the center of the case is Trump’s invocation of the sweeping wartime authority in a 1798 law to let his administration quickly carry out the deportations. Shortly after, civil rights group representing the Venezuelans mounted a legal challenge, and Boasberg said from the bench during a March 15 hearing that any planes carrying migrants deported under the authority must immediately return to the US.

But two such flights carrying more than 100 migrants continued to El Salvador the day of the hearing, and Boasberg promptly embarked on a fact-finding mission about the flights, vowing to “get to the bottom of whether they violated my order – who ordered this and what the consequences will be.”

Attorneys for the Trump administration have argued that Boasberg’s oral command “did not amount to a binding injunction” and that a written order he issued shortly after the proceedings is the controlling ruling in the matter.

That written order contained no such language about the planes and instead just said the administration was enjoined from removing the migrants subject to Trump’s proclamation invoking the law while the judge’s temporary restraining orders remained in effect.

Lawyers from the ACLU and Democracy Forward, which are representing the Venezuelans challenging Trump’s proclamation, counter that the judge’s written order on March 15 encompassed his oral order by including the language, “As discussed in today’s hearing,” and argue that there’s no question that the administration violated the court’s orders.

“The purpose of the Court’s order was unmistakable – to keep individuals from being handed over to a foreign government,” they told Boasberg in court papers. “And counsel for Defendants stated that he ‘understood’ on March 15 that the Court had orally directed the government to turn planes around immediately.”

This story and headline have been updated after Thursday’s hearing.

CNN’s Angelica Franganillo Diaz contributed to this report.

The-CNN-Wire
™ & © 2025 Cable News Network, Inc., a Warner Bros. Discovery Company. All rights reserved.