Less than a month into the second Trump administration, the White House began publicly toying with the idea of defying court orders. In the weeks since then, it’s continued to flirt with the suggestion, not ignoring a judge outright but pushing the boundaries of compliance by searching for loopholes in judicial demands and skirting orders for officials to testify. And now the administration may have taken its biggest step yet toward outright defiance—though, as is typical of the Trump presidency, it has done this in a manner so haphazard and confused that it’s difficult to untangle what actually happened. But even amid that haze, so much is very clear: Donald Trump’s most dangerous tendencies—his hatred of immigrants; his disdain for the legal process; his willingness to push the boundaries of executive authority; and, newly, his appetite for going to war with the courts—are magnifying one another in a uniquely risky way.

The case in question involves Trump’s invocation of the Alien Enemies Act to accelerate deportations of Venezuelan migrants without going through the normal process mandated by immigration law. The statute, which is almost as old as the country itself, has an unsavory pedigree: It was passed in 1798 along with the notorious Alien and Sedition Acts, part of a crackdown on domestic dissent in the midst of rising hostilities between France and the fledgling United States. Before this weekend, it had been used only three times in the country’s history. On Friday, at a speech at the Justice Department—itself a bizarre breach of the tradition of purportedly respecting the department’s independence from the president—Trump hinted that he would soon be invoking the statute, this time against migrants whom the administration had deemed to be members of the Venezuelan gang Tren de Aragua.

From here, the timeline becomes—perhaps intentionally—confusing. At some point over the ensuing 24 hours, though it remains unclear exactly when, Trump signed an executive order to that effect. Before that order was even public, the ACLU filed suit in federal court seeking to block the deportation of five Venezuelans who it believed might be removed. (In a sickening twist, several of the plaintiffs say they are seeking asylum in the United States because of persecution by Tren de Aragua.) By 5 p.m. on Saturday, Judge James Boasberg of the U.S. District Court for the District of Columbia had convened a hearing over Zoom. Things had happened quickly enough that the judge apologized at the beginning of the hearing for his casual appearance; he had departed for a weekend away without packing his judicial robes.

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Thanks to the Alien Enemies Act’s age and sparse use, many of the legal questions around its invocation are novel, and Boasberg admitted to struggling to make sense of these issues so quickly. The broad authority to rapidly remove noncitizens clearly appealed to Trump, who has always been adept at identifying and exploiting grants of executive power that allow him to put pressure on the weak points of the constitutional order. In an additional twist, the administration announced that it would be using this authority not just to deport supposed members of Tren de Aragua who lack U.S. citizenship or permanent residency, but to send them to a horrific Salvadorean mega-prison established by El Salvador’s president, Nayib Bukele, the self-professed “coolest dictator in the world.”

The problem with this clever scheme, as the ACLU argued during the Saturday-evening hearing, is that the Alien Enemies Act does not actually apply to this situation. The statute provides the president with the authority to detain and quickly remove “all natives, citizens, denizens, or subjects” of a “hostile nation or government” in the event of a declared war against the United States or an “invasion or predatory incursion.” The United States is, obviously, not at war with Venezuela; Tren de Aragua, against which the executive order is directed, is not a “nation or government”; and in no reasonable sense is an invasion or incursion taking place. Trump is attempting to get around these many problems by proclaiming Tren de Aragua to be “closely aligned” with Venezuelan President Nicolás Maduro, to the extent that the gang and the Venezuelan government constitute a “hybrid criminal state.” Building on several years of unsuccessful right-wing legal efforts to frame migration across the U.S.-Mexico border as an “invasion,” the executive order likewise frames Tren de Aragua’s presence within the United States as an “invasion or predatory incursion.”

These claims range from weak to laughable, and that’s before we consider the range of other legal problems raised by Trump’s use of the law. The best card the government has to play is the argument that courts simply can’t second-guess the president’s assertions here, based on a 1948 case in which the Supreme Court found that it couldn’t evaluate President Harry Truman’s decision to continue detaining a German citizen under the Alien Enemies Act well after the end of World War II. But the circumstances of that case, Ludecke v. Watkins, were substantially different from the circumstances today. During Saturday’s hearing, Judge Boasberg concluded that the ACLU had made a strong argument that the Alien Enemies Act can’t be invoked against a gang. At the ACLU’s request, the judge not only issued a temporary order barring deportation of the five plaintiffs under the Alien Enemies Act, but also blocked the administration from removing any other Venezuelan migrants from the country on those grounds while litigation continues.

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If the chain of events ended there, this would be a familiar narrative about Trump’s hostility to immigration and his penchant for making aggressive arguments in court. But there is another layer to this story that moves it into the territory of potential crisis. While the timeline remains confused, it appears that at least three planes traveled from the U.S. to El Salvador on Saturday evening, two of them departing during the hearing; all three flights arrived in El Salvador (following stopovers in Honduras) after Boasberg issued both oral and written rulings barring the deportations. A White House spokesperson confirmed to The Washington Post that 137 people on the flights had been deported under the Alien Enemies Act.

President Bukele has adopted a posture of smug mockery toward the court: “Oopsie … Too late,” he posted on X yesterday morning, with a screenshot of a news story about the judge’s ruling. Secretary of State Marco Rubio shared the post. But the Trump administration can’t seem to decide what exactly happened and whether or not what happened was a gutsy commitment to presidential power or, instead, a terrible mistake. An Axios story published last night quotes a jumble of anonymous officials apparently at odds with one another: “It’s the showdown that was always going to happen between the two branches of government,” one official said, while another frantically clarified, “Very important that people understand we are not actively defying court orders.” The administration appears to have settled on the baffling argument that it wasn’t actually defying Judge Boasberg, because the order didn’t apply to planes that were already in the air and outside U.S. territory. To be clear, that is not how things work.

The judge has called for a hearing at 5 p.m. today, when the government will be required to answer a range of questions posed by the ACLU as to when the flights departed and landed and what happened to the people on them. We should pay close attention to what the Justice Department says in court, where lies—unlike quotes to reporters or comments on television—can be punished by judicial sanctions. The administration has talked a big game about its willingness to ignore the courts, but in this instance, it may have engineered a legal crisis at least in part by accident. Will it be able to muster the same audacity when standing in front of a judge?