Photo: Carolyn Van Houten/The Washington Post/Getty Images
The Saturday that Judge James Boasberg, the chief judge of the federal district court in Washington, D.C., was assigned the case challenging Donald Trump’s invocation of the Alien Enemies Act, he was not dressed for the occasion. The case had been filed alongside an urgent motion to prevent the deportation of five people their lawyers feared would soon be disappeared to El Salvador. At an emergency hearing conducted on Zoom that evening, convened to figure out whether judicial intervention was needed to prevent any wrongful deportations, Boasberg had to apologize to everyone present. “I went away for the weekend and brought with me neither a robe nor tie nor appropriate shirt, so thank you all for being appropriately attired and hope you will forgive my casual ones,” he said.
By the end of the hearing, which was adjourned for about an hour so the government could figure out if any planes carrying migrants had departed, Boasberg made up his mind. “I am prepared to rule,” he said, before proceeding to issue a pair of orders preventing anyone covered by the proclamation from being deported. It was followed by this directive: “Any plane containing these folks that is going to take off or is in the air needs to be returned to the United States.” He left the details up to the government. “However that’s accomplished, whether turning around a plane or not embarking anyone on the plane or those people covered by this on the plane, I leave to you. But this is something that you need to make sure is complied with immediately.”
The Trump administration didn’t comply. And in the weeks since, Boasberg and the Justice Department have been in a standoff, with the judge demanding an explanation for why his orders weren’t followed, and the government claiming that once the planes were in the air, there was nothing to be done. “No court has the power to compel the President to return them, and there is no sound basis to read the Court’s minute order as requiring that unprecedented step,” the department wrote last week. On Thursday, Boasberg will hold yet another hearing to get to the bottom of things and potentially determine if holding the government in contempt is warranted.
How Boasberg rules there, and how the administration responds, will be the first true test of whether the constitutional order that Trump has spent every day of his second term attacking will hold. At a moment when people the nation over are being abducted off the streets or receiving notice that their days here are numbered, without a semblance of even an opportunity to be heard, how Boasberg holds the government to our most basic shared commitments may yet set the tone for the next four years.
Trump has called the judge a “radical left lunatic,” a “troublemaker,” and an “agitator,” to name but a few descriptors the president has used in one of his many Truth Social posts complaining about judges who don’t rule as he would like. Boasberg, who has kept a steady hand over every proceeding and ruling since, appears up for the challenge of judging the administration, applying the same rigor to the case that those who have watched him up close have seen in his more than 20 years as a judge.
To wit, in a recent ruling he threaded something of a legal needle. Rather than deciding whether courts have the authority to second-guess a president’s invocation of a wartime statute that “lay dormant for 75 years” following World War II, Boasberg — in a studious 37-page opinion that was rich with facts, law, history, and the judge’s own reservations about “a host of complicated legal issues” — boosted Trump in ways that would shock House Speaker Mike Johnson, who all but threatened to defund the court where the judge sits. He fully affirmed that the law the president invoked, the Alien Enemies Act, is constitutional. He did not question that the president has the authority to detain people subject to the law or a proclamation Trump issued earlier this month invoking it. He also noted that none of his court orders thus far, which the Justice Department has fiercely contested and are now at the Supreme Court, prevented the administration from rapidly deporting people who were, in fact, members of Tren de Aragua, the transnational Venezuelan gang Trump targeted with his proclamation. Or that the government couldn’t apprehend other noncitizens who may be subject to Trump’s proclamation. His own orders, Boasberg added, don’t even require a single person to be released.
After reviewing the relevant precedents, Boasberg only had one objection: “It follows that summary deportation following close on the heels of the Government’s informing an alien that he is subject to the Proclamation — without giving him the opportunity to consider whether to voluntarily self-deport or challenge the basis for the order — is unlawful.” That’s it.
Boasberg has ordered the administration to explain whether his orders have been violated. In response, the government has done everything but cooperate: It has invoked the state-secrets privilege, essentially telling the judge that he’s entitled to no additional information about the flights he ordered returned; has accused him of misconduct and wants him removed from the case; and has argued that a federal court has no power over how the president exercises his authority abroad. In the coming days, the Supreme Court will have a say on how Boasberg has been ruling and conducting himself in these proceedings so far. Implicit in the Court’s judgment, because the issue is not directly before it, is how the weakest and least dangerous branch deals with the branch that wields executive power, controls the military, and has all the guns and the enforcement authority — and is headed by a president who appears ready to defy it.
The judges who work at the E. Barrett Prettyman Courthouse, which is right across the Capitol, are not strangers to high-profile political disputes. Because of their proximity to power, they’re accustomed to legal challenges related to presidential authority, government secrecy, the workings of federal agencies, and the relationship between the three branches of government. But over the past four years, another thing set them apart: Together, they handled more than a thousand prosecutions stemming from the January 6 insurrection — arraignments, bail hearings, trials, guilty pleas, sentencings, appeals, you name it.
In the midst of it all was Boasberg, whose perch as chief judge also gave him visibility into the grand-jury process — a highly secretive endeavor where sometimes witnesses resist subpoenas to testify and choose to litigate them. It was in this capacity that Boasberg ordered former vice-president Mike Pence to testify in the probe led by special counsel Jack Smith. “The bottom line is that conversations exhorting Pence to reject electors on January 6th are not protected,” Boasberg wrote in his 2023 ruling. “There is no dispute in this case that Pence lacked the authority to reject certified electoral votes.” Once Smith secured Trump’s indictment, Boasberg and other judges stood watch in his own packed courtroom as the then-former president was read his charges and pleaded not guilty in front of a magistrate.
A former homicide prosecutor, Boasberg received unanimous confirmation from the Senate when, in 2011, President Barack Obama elevated him from the local Washington court, where he had served for many years as an appointee of George W. Bush, to the federal district court. NBC News recently uncovered a grainy image of Justice Brett Kavanaugh, Boasberg’s friend and roommate at Yale Law School, when the two of them sat side-by-side during an investiture ceremony for Boasberg.
Chief Justice John Roberts, who issued an unusual statement noting that impeachment is not the appropriate course when the government disagrees with a judge’s ruling, is also familiar with Boasberg’s work. The chief has hired law clerks who have worked in the judge’s chambers and also appointed him to the secretive Foreign Intelligence Surveillance Court, which reviews authorization requests for wiretaps and other sensitive methods of foreign-intelligence gathering. In this role, Boasberg oversaw efforts to reform the FBI’s “significant errors and omissions” related to former Trump adviser Carter Page.
No matter who you talk to in Washington legal circles, you’d be hard-pressed to find anyone with anything bad to say about Boasberg, a native Washingtonian whose close associates call “Jeb” and who, at six-foot-six, is said to cut an imposing figure. More than one person, lawyers and judges alike, have told me that they’re glad that this and other Trump-related controversies have landed in his courtroom and not others’. “Given his credibility across the spectrum,” says one lawyer who practices regularly in the district and appeals courts in Washington, “he’s better equipped to withstand these attacks than many would be.”
“Judge Boasberg is one of the finest judges in the United States, period,” says retired circuit judge David Tatel, who served for nearly 30 years in the appeals court in Washington. “I reviewed his work for years. Some of his decisions might be called conservative. Some of them might be called liberal. But they’re all faithful applications of law to the facts before him.”
Indeed, some of his actions in recent years can be characterized as favorable to Trumpworld. To name but a few examples, Boasberg hasn’t gone as harshly as other judges on people convicted over the Capitol riot, he took a hard stance against FBI lawyers involved in the Page affair, and he once rejected a lawsuit to force the IRS to make public Trump’s tax records.
By happenstance, Boasberg was again thrust into the spotlight last week for drawing a case challenging the lawfulness of Signalgate — more specifically, to force the Trump administration to preserve every Signal message sent on the app while The Atlantic’s Jeffrey Goldberg was an unwitting witness to it all. The judge quickly ordered those messages preserved while the litigation plays out. Once again, Trump is none too pleased. “How disgraceful is it that ‘Judge’ James Boasberg has just been given a fourth ‘Trump Case,’ something which is, statistically, IMPOSSIBLE,” the president wrote. As is with every case filed in the federal court in Washington, the case was assigned randomly.
Stephen Vladeck, a Georgetown law professor who has been keeping close track of a number of Trump-related controversies now pending before the Supreme Court, told me that the Venezuelan deportations case Boasberg is overseeing is a touchstone for the rule of law itself. “The Alien Enemy Act case is a flashpoint not only because the legal issues it presents so fundamentally implicate the rule of law in the most elementary sense, but because the Justice Department’s behavior also poses a direct challenge to the ability of even the most principled, well-regarded federal judges to obtain compliance with their mandates,” Vladeck said. “It’s hard to imagine how any other case could so centrally implicate where we are at this moment — and where we’re going.”
