President Donald Trump has had a largely successful year at the Supreme Court, but on Friday, he was handed his first loss in months, and more difficult decisions from the justices appear on the horizon.
Since the Trump administration took office in January, it has petitioned the Supreme Court’s emergency docket more than two dozen times and has been overwhelmingly successful. The administration had a winning streak on the emergency docket dating back to May, but that streak was broken Friday in an immigration judge free speech case, and 2026 could offer more losses at the high court for Trump, as the justices issue opinions on some of his major policies.
Immigration judge free speech petition marks first loss in months
The Trump administration asked the high court to halt the proceedings of a case in federal court challenging a policy requiring immigration judges to receive permission when giving speeches pertaining to their duties. The administration claims a federal appeals court erred by allowing the case to proceed for additional fact-finding in federal court, rather than deferring to the Merit Systems Protection Board, which deals with disputes brought by federal employees.
Chief Justice John Roberts granted an administrative stay on Dec. 5, but the full court later lifted the administrative stay and declined to give the administration its requested pause of proceedings. The unsigned order said the administration’s request came too early in the process and invited it to refile its petition after the case is more developed.
“At this stage, the Government has not demonstrated that it will suffer irreparable harm without a stay. This denial is without prejudice to a reapplication if the District Court commences discovery proceedings before the disposition of the Government’s forthcoming petition for a writ of certiorari,” the Friday order said.
While not a complete loss for the administration, the ruling marked the first time since various immigration related petitions earlier this year that the president has been on the losing side of an emergency docket order.
Prior to Friday, the most recent loss for the administration on the emergency docket was in May when the high court halted deportations under the Alien Enemies Act in Texas. The May order had followed some similar previous orders on deportations and immigration matters, which the Trump administration had been on the losing side of on the emergency docket.
Trump still awaiting decision on National Guard emergency docket case
While the Trump administration racked up its first loss on the emergency docket in months, it has been awaiting a ruling on whether it can deploy troops to Chicago since October. Solicitor General D. John Sauer filed the petition to the court’s emergency docket 66 days ago, longer than the typical six to eight weeks the Supreme Court has taken to respond to Trump petitions this year.
The legal battles over the administration’s use of the National Guard in major cities, where immigration enforcement has been met with unruly protests, have spanned multiple federal courts, but the Chicago case marks the first time the Supreme Court has been asked to weigh in. The deployments in Chicago, Portland, and Los Angeles include federalizing state National Guard troops to defend federal assets and officials, according to the administration.
Trump’s attempt to deploy troops to Chicago was halted by a federal district court, an order which was upheld by a federal appeals court, leading to an emergency petition at the Supreme Court. Sauer urged the justices to lift the court-imposed stay of the deployment, arguing it “improperly impinges on the President’s authority and needlessly endangers federal personnel and property.”
“This case presents what has become a disturbing and recurring pattern: Federal officers are attempting to enforce federal immigration law in an urban area containing significant numbers of illegal aliens,” Sauer wrote in his Oct. 17 petition to the Supreme Court.
“The federal agents’ efforts are met with prolonged, coordinated, violent resistance that threatens their lives and safety and systematically interferes with their ability to enforce federal law,” the petition continued.
After initial briefs were filed by the Justice Department and Illinois officials, the high court requested additional briefs asking whether “regular forces” in the law Trump invoked to deploy the National Guard include the military. The federal statute, 10 U. S. C. §12406, outlines when a president may federalize and deploy the National Guard, including in instances when “the President is unable with the regular forces to execute the laws of the United States.”
The Trump administration argued the military is not included in the “regular forces” mentioned in the federal law outlining when the president can deploy the National Guard, while Illinois officials argued it does include the military.
The Trump administration has faced a mixed bag of rulings in different National Guard cases across different federal courts, with the U.S. Court of Appeals for the Ninth Circuit being the only lone court to allow a deployment — in Los Angeles — to continue in the interim.
There is no set timeline for the Supreme Court to issue orders regarding emergency petitions, meaning an order on the petition could come at any time.
Tariffs, birthright citizenship, and Federal Reserve firing could be difficult decisions for Trump
While the emergency docket has offered up several wins for Trump early in his second term, the Supreme Court’s merits docket appears poised to offer some high-profile losses in 2026.
The administration is currently awaiting decisions on the president’s sweeping “Liberation Day” tariffs and on whether the president can fire independent agency heads without cause, after oral arguments in both cases were held in late 2025. In the first several months of 2026, the high court will hear arguments over whether Trump’s birthright citizenship order is constitutional and an emergency docket case over whether to allow the firing of Federal Reserve governor Lisa Cook, which Trump claims he properly did for cause.
During arguments in the tariffs case, the justices appeared skeptical of the administration’s arguments that the president had the power to issue sweeping tariffs under the International Emergency Economic Powers Act. The justices did appear likely to side with the administration on the president’s view of firing independent agency heads, after previously siding with Trump multiple times on the emergency docket on the matter.
SUPREME COURT GRAPPLES WITH HOW MUCH EXECUTIVE POWER INDEPENDENT AGENCIES REALLY EXERT
The birthright citizenship case is expected to be an uphill battle for the Trump administration, after the executive order was struck down by various courts as unconstitutional.
After a busy year at the Supreme Court in 2025, the Trump administration is hoping to continue its overwhelmingly positive record among the justices into 2026, despite the end of the winning streak in the closing months of the year.
