President Donald Trump appears to be losing his grip on the Supreme Court.
After notable victories during his first year in office, Trump has faced significant resistance from judges in recent months, including a crushing defeat on his tariff policy. Arguments in the high court on Wednesday revealed that another loss could be looming over his effort to end birthright citizenship for undocumented immigrants and foreigners on short-term visas.
Trump emerged victorious in some of the nearly 30 emergency appeals filed with the high court last year on issues ranging from immigration to mass firings of federal employees to the sudden end of billions of dollars of federal grants and contracts.
Critics, including some liberal judges, said the high court was being too deferential and treating every lower court’s rebuke of Trump policy as a national emergency worthy of immediate action.
But the rejection of Trump’s signature tariff program and the administration’s use of the National Guard to control anti-ICE protests, as well as the president’s tough trip this week to the birther policy, are challenging the notion that the court is firmly in Trump’s pocket.
“I don’t think it’s possible for this administration to perform as well on the court going forward as it has done over the last 14 months, partly because it’s hard for them to perform better over the last 14 months,” said Stephen Vladeck, a Georgetown law professor and leading critic of the court’s handling of the so-called shadow docket.
Legal experts said that, as the court moves away from fast-moving emergency appeals to hearing cases in the more time-intensive regular process, the administration is likely to face greater resistance from judges.
“It’s going to be very difficult and the administration is going to win some, but they’re also going to lose some,” said Roman Martinez, who clerked for Chief Justice John Roberts and Justice Brett Kavanaugh when he was an appeals court judge.
“The big lesson here is that the court is going to be more skeptical of the administration on the merits than on the shadow side,” Vladeck said.
john sawyer’s secret weapon
A major factor creating more pain for Trump in court is his lawyers’ loss of control over which cases come before judges. When the administration’s initial policies were blocked by federal judges, Solicitor General John Sawyer decided which cases should be taken on emergency appeal to the Supreme Court and which cases should be allowed to languish in lower courts.
As Sawyer’s team looked at the many injunctions issued by district court judges, Justice Department lawyers prioritized cases where they had a good chance of winning emergency relief.
Other cases, some of which were high-profile, were not referred to court. In particular, the administration missed the chance to file an emergency appeal to the Supreme Court against orders blocking Trump’s crackdown on Harvard University and his attempt to close several major law firms.
“If you just look at the win-loss tracker, yes, it was great for the administration through most of 2025, but the sample set was not a random selection of cases,” said Martinez, who worked in the solicitor general’s office during the Obama administration. “This was the set of cases that President Trump’s legal team chose to take to court. And those lawyers were savvy and selective, they chose to appeal cases where their positions were inherently stronger.”
choices become difficult
As cases progress, the choices for the government become increasingly difficult, with officials often forced to decide between taking their chances at the Supreme Court or abandoning a policy altogether. Additionally, cases that reach the court on an emergency basis often return for full briefing and arguments.
“At the beginning of the process, it’s more the case that the Solicitor General can dominate that conversation. But as cases come back to court later, the SG loses a fair amount of control,” Vladeck said.
As the process progresses, Sawyer may continue to try to influence which cases reach the court, but he may not always succeed.
A clear example of this came last month when the Trump administration informed the D.C. Circuit Court of Appeals that the administration is no longer seeking to revive Trump’s executive orders attacking specific law firms — orders that were similarly blocked by district court judges.
The move required Sawyer’s approval, which could have led to a potentially negative ruling on the issue from the appeals court. However, the following day, the Justice Department reversed its stance and announced that it would continue the appeal. It gave the court no explanation for the reversal, but The Wall Street Journal reported Trump claimed he was never consulted about the decision to withdraw.
A White House official, who was granted anonymity to discuss internal deliberations, said the initial filing was due to an omission. “No final decision was made and there was an inadvertent filing that was rectified,” the official said.
Justice Department spokespeople did not respond to requests for comment.
Sawyer suggested that he is aware that he may face a more difficult workload on the high court this year than in Trump’s first year in office.
At a conference of judges last September, Sawyer joked that he now faced the “terrible” prospect of full arguments on all the emergency cases Trump won during his first months in office.
“Who will debate all these matters…?” Sawyer asked.
