The Courts Versus Trump, Then and Now

On April 11, the day after the Supreme Court issued an emergency ruling in Noem v. Abrego Garcia, requiring the Trump administration to “facilitate” the return to the United States of a Maryland man shipped to a Salvadoran prison, a journalist aboard Air Force One asked President Trump if he intended to comply with the Court’s ruling. “If the Supreme Court said bring somebody back, I would do that,” Trump said. “I respect the Supreme Court.”

And what about the lower court, the journalist asked—pointing to the orders by District Judge Paula Xinis, following the Supreme Court’s ruling.

“Oh, no, no,” Trump clarified. “I’m not talking about the lower court. I have great respect for the Supreme Court.”

The administration’s handling of Abrego Garcia and related cases concerning immigrants sent to El Salvador is, so far, the most ominous signal yet in terms of the relationship between the executive branch and the judiciary, from the Supreme Court down to district judges. The Justice Department has repeatedly dodged requests for information from lower court judges and pushed the boundaries of compliance with the Supreme Court’s orders in both Abrego Garcia and J.G.G. v. Trump, the first case that came before the Court concerning the Alien Enemies Act. But the Alien Enemies Act litigation is only the most extreme example of a broader pattern of government defiance in front of the courts. Just three months into the second Trump administration, it’s become commonplace for judges to excoriate Justice Department lawyers for their inability to clarify basic facts, explain the administration's actions, or provide anything in the way of convincing reasoning to justify their litigating position.

During Trump’s first term in office, the judiciary struggled with how best to approach its interactions with a chief executive unconstrained by fact and unbound from any concern with honoring his oath of office. Should such an administration be granted the traditional deference accorded to the executive branch on matters of national security and foreign policy? Should it enjoy the benefit of the doubt that courts typically bestow when they assume that government officials have acted lawfully? How aggressively can or should courts probe the reasoning that the administration puts forward in court—especially when statements made by Justice Department lawyers to judges are regularly contradicted by the administration in comments outside the courtroom?

From 2017 through 2021, courts wrestled with these issues but never managed to resolve them in a satisfactory or systematic manner. Now, with the second Trump administration flirting with a far more confrontational approach to the courts than the first administration ever did, the question of how the judiciary should engage an aberrant presidency has only grown in urgency and importance. Judges during the first Trump term had to weigh how to handle actions that might well have been plausible uses of executive power if carried out by any other president but were tarred by Trump’s involvement. Now, during the first few months of the second Trump administration, the problem is how to handle actions that no modern executive other than Trump would ever have dreamed of.

Last month on Lawfare, Alan Rozenshtein examined the status of the “presumption of regularity”—the principle that, as the Supreme Court defined it in 1926, “in the absence of clear evidence to the contrary, courts presume that [government officials] have properly discharged their official duties.” In Rozenshtein’s view, the second Trump administration’s aggressive posture in front of the courts has arguably pushed the presumption into “free fall,” with judges increasingly expressing frustration with the executive’s evasiveness and even mendacity. Here, I want to take a slightly different approach to a similar question. How, in practice, did courts express their ambient distrust of the first Trump administration, and how does that compare to the actions they’ve taken this time around?

The strain between Trump and the judiciary became apparent within weeks of the 45th president’s entry into office. On Jan. 27, 2017, Trump issued the first travel ban barring citizens from seven majority-Muslim countries—“we all know what that means,” he commented after reading out the ban’s stated intent of “protecting the nation from foreign terrorist entry”—which courts rapidly blocked within hours of its implementation, as travelers found themselves stranded in airports across the country. As Benjamin Wittes and I wrote at the time, as the litigation over the travel ban wound on, judges at both the district and appeals levels continued to rule aggressively against the administration, even after the White House unveiled a newer and better-lawyered version of the ban. Given the far more careful wording of the second executive order, and the ban’s location at the intersection of two areas in which courts are inclined to defer to executive authority—national security and immigration enforcement—one might have expected courts to back off.

Instead, they dug in, ruling with what immigration law expert Peter Margulies described as a “marked lack of deference.” In one May 2017 en banc ruling upholding an injunction against the second iteration of the ban, the U.S. Court of Appeals for the Fourth Circuit cited Ex parte Milligan to argue that “the question for this Court, distilled to its essential form, is whether the Constitution … remains ‘a law for rulers and people, equally in war and in peace’”—a rhetorically striking choice, but legally, as Andrew Kent noted at the time, a bit of a stretch. The en banc court likewise pointed to a pair of precedents typically relied upon as counseling judicial deference to the political branches on matters of immigration (Kleindienst v. Mandel and Kerry v. Din) and instead leveraged them to suggest an authority to look behind the executive’s proffered reasoning to investigate bad faith.

The Supreme Court, of course, ultimately upheld the constitutionality of the third iteration of the ban, although it did so in conjunction with expressions of anxiety from Chief Justice John Roberts (writing for the majority) and Justice Anthony Kennedy about the divergence between the crass and hateful actions of the president and the Constitution’s more elevated expectations of the person occupying that office. A year later, though, Roberts himself would move toward a more flexible approach in order to push back against obvious bad faith on the part of the administration. In the census case, Dept. of Commerce v. New York, the chief justice crafted a majority opinion that probed beyond the pretextual justification offered by the administration for adding a citizenship question to the census, reasoning: “If judicial review is to be more than an empty ritual, it must demand something better than the explanation offered for the action taken in this case.”

As Justice Clarence Thomas noted in a somewhat irritated concurrence, this broke new legal ground in allowing judicial investigations of agency decision-making processes. Thomas pointed to the presumption of regularity in his concurrence, arguing that Roberts’s inquiry into pretext “offends” that presumption. As Aram Gavoor and Steve Platt write in their study of the idea, the presumption of regularity is not particularly well-defined: They describe it as “a multidimensional deference principle with undemarcated boundaries,” across both civil and criminal law, that the executive branch is basically trustworthy and does as it says. The legal battle over the travel ban could be described as not only a fight over immigration law but also a fight over what the presumption of regularity actually means, and what it takes for that presumption to be overcome. On one side, proponents of the courts’ power to peek behind “the explanation offered” by the government in court; on the other, those who claim that courts must accept precisely what the government tells them.

The presumption is a useful way of conceptualizing the overall problem that courts faced in confronting the fact that they simply could not trust that the first Trump administration meant what it said in court. There are other frameworks for understanding this difficulty, too, and for seeking to understand what it meant for courts to view the executive branch with renewed skepticism. Wittes and I, for example, suggested that we might understand this judicial scrutiny as an expression of lack of faith in the president’s ability to uphold his oath.

In the years since 2017, a number of legal scholars have suggested alternative modes of addressing the issue. Daphna Renan suggests that indications of “institutional collapse” within the executive branch might “cause a court to adjust its own structural norms of deference,” although she notes that there is no “neat formula” available. Drawing on Renan, and with the presumption of regularity as a starting place, Samuel Issacharoff and Trevor Morrison write that judges might adopt “a presumption of a constitutional safe harbor when government actors perform within established frameworks”—and wield increased skepticism if the executive’s actions are “in direct repudiation of similarly well-settled and publicly understood norms or practices.” Kate Shaw asks what form this skepticism might take for lower courts tasked with “evaluating internal executive-branch decisions and decisional processes.” Sandy Levinson and Mark Graber, meanwhile, take the view that the tenure in office of an “anti-Publian president” should push courts to adopt a kind of presumption of irregularity. Rozenshtein, for his part, examines the role of executive “virtue,” and what it means when the courts can see that the president doesn’t have any.

There’s a great deal to be said about all these different approaches. My point here, though, is less to provide a literature review and more to underline that the first Trump administration unsettled core judicial assumptions about the functioning of the executive branch—assumptions that have proved to be so foundational that scholars are still trying to untangle what it means now that they’ve turned out to be shaky.

Courts, too, are still trying to untangle this issue. What I’ve sketched out here might give the impression of a relatively linear story: Over the course of the first Trump administration, judges, including on the Supreme Court, grew increasingly skeptical of the administration and increasingly willing to investigate bad-faith claims. (Gavoor and Platt, for example, suggest that the presumption of regularity proved more durable than someone who examined only those first few months of litigation against the first Trump administration might have expected.) The overall process was more of a confused push and pull as district judges struggled to adapt to unusual legal and political circumstances and found their approaches sometimes slapped down, and sometimes embraced, by higher courts.

Likewise, the Supreme Court did not always stick with the skepticism it embraced in the census case. The justices repeatedly handed Trump victories as his administration went on—particularly on the Court’s emergency docket, where the conservative majority often intervened to allow controversial policies blocked by the lower courts to go into effect. And over the course of the Biden administration, the aberrant behavior of the first Trump administration seemed to fade from the justices’ memories. Consider the Court’s 2024 ruling establishing broad presidential immunity from criminal prosecution, which betrayed a striking willingness on the part of the majority to ignore the potential implications of how a malicious chief executive might abuse that power—or at least to forget that this concern had been squarely before them just a few years prior. Perhaps, having experienced four years of an executive branch functioning within normal boundaries, the need for judicial tools to respond to an out-of-control executive appeared less urgent to the conservative justices, and Special Counsel Jack Smith’s decision to charge Trump over his engineering of the Jan. 6 riot itself appeared to be the aberration.

This, then, was the state of affairs heading into the second Trump administration: a judiciary operating with some experience in handling an aberrant executive, but an experience that remained undertheorized and provided little in the way of a road map for navigating future crises. Three months later, where do things stand?

Anyone who had been hopeful that a second Trump administration would prove more circumspect than the first is, at this point, surely disappointed. The administration has been on a rampage, and the tally of court rulings against it reflects as much. It has been blocked from slashing grant awards to universities, freezing trillions of dollars in federal funds, refusing to provide Maine with money to feed schoolchildren, punishing law firms, suspending refugee admissions, barring the Associated Press from the White House press pool, dismantling the Consumer Financial Protection Bureau, forbidding transgender people from serving in the military, deleting public health data from government web pages, refusing to honor the Constitution’s guarantee of birthright citizenship, … and so on. By one count, judges have granted over 90 temporary restraining orders or preliminary injunctions. A preliminary overview by the political scientist Adam Bonica, conducted in late March, found that Trump’s losses in court thus far have been dealt equally by judges across the political spectrum.

We are, to be sure, in early days yet. But my sense is that while courts are pushing back aggressively against the administration, they are not coming up against doctrinal limits as they did in 2017. During the first months of the first Trump administration, judges weighing the legality of the travel ban had to ask themselves what to do about an executive order that appeared facially lawful but that was obviously motivated in fact by malice. Today, there’s less of a need to investigate pretext, because the extreme and aberrant nature of what Trump is attempting is right there on the surface—and in many cases, the administration is outright gloating over that abuse of power. This is the difference between an administration that leveraged the Justice Department’s Office of Legal Counsel (OLC) to cobble together arguments for poorly-thought-through and malicious policies, and an administration that is reportedly ignoring OLC altogether in favor of just doing whatever it wants.

To put it another way, a judge analyzing a facially neutral executive order, who must weigh whether a president’s campaign-trail and off-the-cuff comments may be considered as evidence of anti-Muslim animus, has a genuinely difficult job. A judge considering whether a president may unilaterally terminate the Constitution’s guarantee of birthright citizenship, in contrast, has a very easy one. So, too, does a judge ruling on an executive order that explicitly states that the White House is seeking to punish law firms on constitutionally impermissible grounds. There’s no longer any need to question whether the judge can permissibly examine the president’s comments outside court, because the retaliatory purpose of the order is right there in the text itself.

As Rozenshtein notes, judges have also grown more and more willing to express distaste and distrust toward the government in what arguably constitutes an erosion of the presumption of regularity—operating at a speed that far outpaces anything that took place during the first Trump administration. “The Court is left with little confidence that the defense can be trusted to tell the truth about anything,” wrote Judge Amy Berman Jackson of the Consumer Financial Protection Bureau (CFPB), granting a preliminary injunction against the attempted dismantling of the agency. Judge Loren AliKhan explicitly denied the government a “presumption of good faith” in choosing to extend a temporary restraining order against the Office of Management and Budget’s (OMB’s) blanket freeze of federal funds, rather than accept the administration’s arguments that its rescission of the OMB memo in question rendered the case moot. Judge Beryl Howell, confronted with internal government guidance that seemed to undercut the executive’s claims of compliance with a temporary restraining order in Perkins Coie’s lawsuit over a retaliatory executive order, warned that the government’s conduct “raised some concern about the general presumption by courts ‘that executive officials will act in good faith.’” In both J.G.G. and Abrego Garcia, Judges James Boasberg and Paula Xinis have excoriated the Justice Department’s bad faith and have made movements toward finding administration officials to be in contempt of court.

To some extent, courts also have more tools in their judicial toolkit than they did during Trump’s first term. Some judges have cited the Supreme Court’s census ruling as grounds for closer examination of the administration’s behavior—such as District Judge Mary McElroy, who pointed to Department of Commerce in holding that the government had unlawfully frozen grants set to be distributed under the Inflation Reduction Act. The end of Chevron deference, which the Supreme Court brought about in its 2024 ruling in Loper Bright Enterprises v. Raimondo, has also allowed judges to look more carefully at agency actions. Most notably, Judge Harvey Wilkinson of the U.S. Court of Appeals for the Fourth Circuit drew on Loper Bright in rejecting the government’s cramped view of the Supreme Court’s order to “facilitate” Abrego Garcia’s return to the United States. (The Justice Department had derived that reading of “facilitate” from an internal Immigrations and Customs Enforcement directive.)

These examples suggest a key distinction between the judicial response to Trump’s first term and to his second. This time, judges’ aggressiveness has appeared less in the substance of their rulings and more when it comes both to remedies and to the sheer pace of litigation. Courts have moved with astonishing speed: Judge Howell, for example, granted Perkins Coie’s motion for summary judgment less than two months after the firm filed the case. Often, courts have worked with particular rapidity as a means of responding to the administration’s newfound tactic of rushing to carry out its goals—bundling Venezuelan detainees onto planes, seizing control of agencies, and dismissing civil servants—in the time before a judge can rule.

“If the defendants are not enjoined, they will eliminate the agency before the Court has the opportunity to decide whether the law permits them to do it,” Judge Jackson explained in her order granting the CFPB injunction. Likewise, in the Alien Enemies Act cases, judges like Boasberg have been quick to grant temporary restraining orders in an attempt to prevent the administration from shipping Venezuelans to a Salvadoran prison with no assurance that they will ever be released. Boasberg himself took the step of rapidly certifying a class—all detained noncitizens potentially subject to removal under the Alien Enemies Act—within hours of a motion by the ACLU, and judges in other Alien Enemies Act cases have since moved with remarkable speed to certify classes in habeas proceedings. Meanwhile, in habeas cases filed by immigrants stripped of their green cards and visas for pro-Palestinian advocacy, federal district judges have quickly issued temporary restraining orders against petitioners’ removal from the country.

This doesn’t mean that the administration has lost every battle. Boasberg, for example, recently declined to grant the ACLU’s motion for a mandated, countrywide 30-day notice period before the removal of any Venezuelans under the Alien Enemies Act. Judge Howell likewise denied a motion for a temporary restraining order that would have blocked Elon Musk’s Department of Government Efficiency initiative from dismantling the U.S. Institute of Peace. In both cases, the judges seemed genuinely appalled by the administration’s conduct, but felt they lacked the power to act. But such instances are, by far, the exception.

This bloodbath in the lower courts made the contrast with the Supreme Court all the more noticeable. Several early rulings on the shadow docket arguably treated the second Trump administration with the same presumption of regularity enjoyed by any president—as in J.G.G., where the Court’s insistence that Alien Enemies Act cases be addressed through habeas alone has provided the government with wiggle room to continue attempting further removals. There was an echo here of the dynamics between the Supreme Court and the lower courts in the travel ban cases, in which a majority of the justices overturned rulings finding the ban unconstitutional.

That is, until recently. The Court’s ruling in Abrego Garcia and its recent decision in a second Alien Enemies Act case, blocking the administration from removing a second tranche of Venezuelans with little notice, might suggest a new willingness to recognize Trump’s games for what they are and deny the administration the presumption of regularity. Here, the echo is of the census case. In that instance, Roberts insisted that the Court was, in the words of Judge Henry Friendly, “not required to exhibit a naiveté from which ordinary citizens are free.”

During the first Trump administration, judges never quite figured out how to theorize an expression of that skepticism. We are months into the second Trump administration, and a great deal depends on the ability and willingness of the courts to counter this onslaught from the executive with both speed and coordination—both areas that are not, traditionally, the judiciary’s forte. In the meantime, Trump and those around him have shown a frightening willingness to attack the authority of the judiciary itself, accusing judges of overstepping their authority and hinting at outright defiance of court orders. This possibility, too, will surely be on the minds of judges as they weigh whether the administration deserves their trust.