Remember when Donald Trump told people that they’d get tired of winning once he was in office? If you are a Trump Administration lawyer, it surely doesn’t feel that way. Based on the useful litigation tracker compiled by the group Just Security, the Trump Administration, in its second incarnation, has lost in thirty-six of fifty-six cases decided so far in the federal district courts and not yet subject to appellate rulings. It has lost in ten of fifteen cases that have been decided at the next level of review, the federal circuit courts of appeals. These numbers are especially striking because the cases are at a preliminary stage, when the hurdles are high for those seeking to block an Administration action.
With six emergency petitions challenging four different Administration policies now before the Supreme Court, the coming days should provide a better sense of how Trump will fare there. The early indications are not good for the Administration: the Court effectively rebuffed a request for emergency intervention involving the U.S. Agency for International Development, albeit by a vote of 5–4. In another case, a challenge to Trump’s order restricting birthright citizenship, the Court set a briefing schedule so languid—those opposing the Administration’s position were given two full weeks to respond—as to send the unmistakable message that the Justices did not share Trump’s view on the urgency of the situation.
These statistics don’t merely indicate that the Administration is on the wrong side of the law. They also reflect bad lawyering. The Administration’s hyper-aggressive litigation strategy combines maximalist assertions of the scope of Presidential power with the insistence that any potential intrusion on executive authority necessitates emergency relief. It is belligerent in tone, treating federal judges like junior associates at law firms, when not asserting that they are biased partisans. It dispatches attorneys like so much legal cannon fodder, to defend the Administration’s actions with little or incorrect information about the underlying facts. It is grudging, if that, on compliance with court orders, all but inviting judges to find the Administration in contempt of court. Add to this Trump’s out-of-court behavior, which has included assailing a respected district-court judge as a “radical left lunatic,” calling for his impeachment, and going after Big Law with blatantly unconstitutional executive orders. An Administration that is going to want the vote of Chief Justice John Roberts might do well to recall that Roberts spent years in private law practice.
One lawyer leading the anti-Trump advocacy surmised that the Justice Department is “trying to play to Trump, and Stephen Miller,” the deputy White House chief of staff. “It’s a very bad strategy,” the attorney added. “We’re by the day gaining more credibility with the Supreme Court by just not being crazy about court orders and judges.” Jack Goldsmith, a professor at Harvard Law School and a senior official in the Justice Department under George W. Bush, has reached the same conclusion. The Trump Administration’s “open disrespect toward and aggressive political attacks on lower court judges will surely have a negative impact on the way that some and maybe most Supreme Court Justices approach the legal issues coming to the Court,” Goldsmith wrote last month on his Substack, Executive Functions. The Justice Department did not respond to a request for comment.
One possible explanation for this self-defeating behavior is that the Trump Administration doesn’t actually care about winning—at least, not about winning in court. It cares about inflicting damage, as swiftly and brutally as possible—putting agencies “into the wood chipper,” for example, as Elon Musk boasted about U.S.A.I.D. Perhaps the Administration will eventually lose in court, but the harm already done will be irreparable. Meanwhile, this argument goes, the Administration reaps political benefit by picking fights on base-friendly issues such as immigration and transgender rights, and by waging rhetorical war against judges. Calls for impeachment now, impeachment forever will result in zero actual impeachments, but they serve as invigorating rallying cries.
Maybe this is the Administration’s approach; in that case, it’s important to acknowledge that there can be a divergence between the tactics that sober-minded lawyers would prefer and the demands of their hot-headed clients. When your hot-headed client is the President of the United States, you can do only so much. That reality was evident in February, early in the litigation wars, when the acting Solicitor General, Sarah Harris, felt compelled to drop a soothing footnote in an emergency request that the Supreme Court block a lower-court order reinstating Hampton Dellinger as the head of the Office of Special Counsel. “The Executive Branch takes seriously its constitutional duty to comply with the orders of Article III courts,” Harris, a former law clerk to Justice Clarence Thomas, assured the Justices. (Dellinger has since withdrawn the appeal, which he appeared destined to lose.)
This observation was no random aside—it followed the President’s alarming statement, on social media, that “He who saves his Country does not violate any Law. ” In an earlier post, Vice-President J. D. Vance, a graduate of Yale Law School, asserted that “judges aren’t allowed to control the executive’s legitimate power.” Proclamations like these are not helpful when you are trying to convince judges that the executive is making a legitimate assertion of power. In the end, as Chief Justice John Marshall declared in Marbury v. Madison, “It is emphatically the province and duty of the judicial department to say what the law is.”
Putting aside the prospect that Trump will resort to open defiance of the Court, the fact is that the courts will be the final arbiter of whether Trump can revoke the constitutional guarantee of birthright citizenship, unilaterally shutter departments created by Congress, fire commissioners at independent agencies without cause, ban trans people from serving in the military, punish law firms because of whom they hire or what clients they represent, or—well, the list goes on. On some of these initiatives, such as the power to control independent agencies, the Administration is likely to encounter a receptive audience, especially before the high court. On others, such as birthright citizenship, the Administration has a tougher path to victory. Making preposterous arguments, employing disrespectful language, and treating judges like obstreperous obstacles rather than life-tenured members of a coequal branch does nothing to help its cause.
In one case—which challenges the removal of Venezuelan migrants accused of being gang members, under the supposed authority of the Alien Enemies Act, a 1798 law that has only been used in wartime—U.S. District Judge James Boasberg unloaded on a lawyer for the government for using “intemperate and disrespectful language I’m not used to hearing from the United States.” In a hearing Thursday, Boasberg, saying the government had “acted in bad faith,” appeared inclined to find it in contempt of an order he had issued not to remove the migrants.
In another case, involving Musk and the Department of Government Efficiency, or DOGE, U.S. District Judge Tanya Chutkan ruled for the Administration, but she admonished lawyers for being disingenuous about the extent of DOGE’s authority over personnel actions. “Defense counsel is reminded of their duty to make truthful representations to the court,” Chutkan wrote in a footnote. Another judge in the District of Columbia, Ana Reyes, was even sharper in response to the government’s argument that its executive order barring transgender individuals from serving in the military applied only to people with gender dysphoria—notwithstanding a tweet from Defense Secretary Pete Hegseth and the Defense Department’s official account asserting flatly, “Transgender troops are disqualified from service without an exemption.”
