A judge told Trump to halt deportation flights. They went ahead anyway.

A legal showdown this past weekend shows that the Trump administration is continuing to test the limits of how far they can get away with ignoring or defying court orders.

On Saturday, Trump officials attempted to rapidly deport a bunch of people they said were Venezuelan gang members to El Salvador — based on a new and initially secret legal rationale — before progressive activists could sue and judges could stop them.

However, the activists did sue and, while deportation flights were either in the air or about to leave, a judge did issue an order to stop them.

But the administration ignored the judge’s order and refused to turn around or halt the flights, which handed over a reported 261 immigrants into Salvadoran custody.

Trump officials cited a few reasons for letting the deportations proceed. One is that, because two of the flights had already departed US territory, the judge’s order (they claim) no longer bound them. They’ve also asserted that the new legal authority Trump invoked — an obscure, rarely-used law known as the Alien Enemies Act — is un-reviewable by federal courts.

Notably, Trump officials seem hesitant to say they were flat-out defying a court order. After an Axios story making that claim was published, it was updated with an anonymous official’s statement: “Very important that people understand we are not actively defying court orders.” But the story makes clear they had the court order in hand and chose to ignore it.

Indeed, the way the Trump administration’s challenge to judicial authority has played out is not through open defiance — there’s no bold “I am defying the courts” announcement. Rather, it’s through sneakily trying to get away with things, pushing the limits, looking for edge cases, and finding whatever legal justification they think seems even remotely defensible.

For instance: They thought they could get away with those in-progress deportations on Saturday. But there hasn’t been news of further Alien Enemies Act deportations since then — and, if they have stopped for now, they are at least putting on a show of belatedly obeying the judge’s order, while appealing it and hoping for the Supreme Court’s eventual blessing.

The tangled series of events involving Saturday’s deportations and a judge’s attempt to stop them

On Friday, Trump secretly signed an order saying he’d assert authority under the Alien Enemies Act — a 1798 law only invoked three times before — to rapidly deport members of the Venezuelan Tren de Aragua gang. Trump officials were trying to send them to El Salvador (where President Nayib Bukele has agreed to accept US deportees), quickly, before they could challenge their deportations in court, make any defense, or argue they were falsely accused.

However, news of Trump’s intention to do this had leaked earlier that week. And, believing the order was imminent, progressive activists filed a lawsuit Saturday morning on behalf of five Venezuelan plaintiffs in US federal custody who feared deportation. US District Judge James Boasberg quickly ordered that those five plaintiffs could not be deported for 14 days, and set a hearing on the topic for late Saturday afternoon. 

Yet Boasberg’s initial order did not fully block Trump’s invocation of the Alien Enemies Act — because he didn’t yet know Trump had already invoked it.

Later Saturday afternoon, shortly before the hearing began, the Trump administration made the Alien Enemies Act proclamation public. Then, while the hearing was underway, two deportation flights departed the US, headed for El Salvador. 

Around 6:47 pm Eastern time, Boasberg issued a verbal order blocking all deportations under the Alien Enemies Act (not just those of the five plaintiffs). He specified that his order may entail turning planes around. He issued his order in writing at 7:26 pm Eastern time.

At that point, the two deportation flights had left US territory. Trump officials discussed what to do and decided not to turn those flights around. Additionally, a third deportation flight reportedly departed the US shortly after Boasberg’s order was issued.

All three flights eventually landed in El Salvador, where 261 immigrants — mostly Venezuelans, but also some Salvadorans — were turned over to Salvadoran custody. A Trump official told the Washington Post that 137 of them were deported under Alien Enemies Act authority, with the rest being deported under other legal authority. (The five Venezuelans who sued were not deported and remain in US custody.)

Trump officials’ claims about what happened here will soon be scrutinized in court

Per Axios’s Marc Caputo, White House deputy chief of staff for policy Stephen Miller “orchestrated” all this with Homeland Security Secretary Kristi Noem. Caputo’s sources claim their goal was to have the deportations already finished before any judge stopped them — and they were somewhat foiled. “We wanted them on the ground first, before a judge could get the case, but this is how it worked out,” an anonymous official told him.

Furthermore, Caputo’s administration sources claim that they only declined to order the planes back “on advice of counsel,” with the fact that two planes were over international waters being decisive. But this would not justify allowing the third flight to depart the US shortly after Boasberg’s order.

More details may be coming soon, as Boasberg has scheduled another late afternoon hearing Monday to question whether the administration complied with his order. For now, though, this seems like the latest effort from the Trump administration to test the limits of what they can get away with in defying the courts. Which means we may find out what, if anything, the courts can do in response.