The Biggest Damn Fool Mistake: Trump and the Roberts Court

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Today the Supreme Court opens its October 2026 Term, though the idea of a term with a beginning and an end is mostly ceremony now. In the shadow docket era, the Court decides important and complicated issues without full briefing or oral argument, and often with the justices languishing at luxury getaways, domestic and abroad, some of them subsidized by Harlan Crow or Paul Singer. Since the last term's final opinions came down, the Court has let construction of the President's ballroom continue on the ruins of the East Wing, and it allowed deportations to third countries to resume over a lower court's finding that migrants were not getting a fair chance to raise fear of torture.

And yet the President cries foul. Asked by Time whether he regrets nominating Neil Gorsuch, Brett Kavanaugh, and Amy Coney Barrett, Trump said: "Yeah. Yeah. What can I do? I put them in. They voted against me too often." He added, "I do like loyalty, yeah." Two weeks earlier, after the Court refused to let the Postal Service rewrite mail-ballot rules fifty days before the midterms, he posted: "These are not the people I interviewed to serve on the United States Supreme Court, they are merely a shell of their original selves."

If only.

In under six years in the White House, Trump has named a third of the Court. Jimmy Carter served four years and named no one. Trump had considerable help. In 2016, Mitch McConnell held Justice Antonin Scalia's seat open for almost a year so the voters could decide. In 2020, with Justice Ruth Bader Ginsburg's seat open and ballots already being cast, Justice Barrett was nominated and confirmed in a manner of weeks.

Dwight Eisenhower is said to have called his choice of Earl Warren "the biggest damn fool mistake I ever made." Historians debate whether he said it; nobody debates the disappointment. Chief Justice Warren, a former Republican governor, wrote Brown v. Board of Education (the unanimous 1954 ruling ending legally mandated school segregation) and led the most liberal (maybe the only liberal) Court in American history. A second line, "I have made two mistakes, and they are both sitting on the Supreme Court," adding Justice William Brennan, rests on thinner evidence still, though a 1957 diary entry by Justice Harold Burton confirms Ike's "disappointment" with both.

Nixon picked Harry Blackmun, who wrote Roe v. Wade three years later. Ronald Reagan nominated Anthony Kennedy who wrote the only four Supreme Court decisions in American history affirming the rights of gays and lesbians. George H.W. Bush's chief of staff called David Souter a "home run" for conservatives. Two years later Souter co-wrote the opinion partially reaffirming Roe in Planned Parenthood v. Casey, and the right adopted a rallying cry: "No more Souters."

Against those benchmarks, the distance between what Trump wanted from his three justices and what he received is barely a rounding error.

With all three in the majority, the Court gave him criminal immunity in Trump v. United States, making him the only president in history to benefit from a shield he is now putting to use in myriad ways. In Trump v. CASA, written by Barrett, the Court ended the nationwide injunctions lower courts had used to halt Trump’s policies. Just this year, it overruled a 90-year-old precedent in Trump v. Slaughter (holding that the President may fire the heads of independent agencies at will), and in Mullin v. Doe it cleared the way for Trump to strip Temporary Protected Status from roughly 350,000 Haitians and 6,000 Syrians while barring courts from reviewing most of how the government got there. A year ago, in Noemv. Vasquez Perdomo, it cleared the way for roving immigration sweeps in Los Angeles, and Justice Kavanaugh wrote that "apparent ethnicity" could be a "relevant factor" in a stop, giving the country the phrase "Kavanaugh stops."

On the emergency docket, Trump's administrations have filed 82 applications in under six years, 41 in his first term and 41 more in less than two years of his second. The Bush, Obama, and Biden administrations filed 27 combined, across twenty years. Lower courts, including his own appointees, rule against Trump far more often than the Supreme Court. A Court Accountability study found he wins about nine times in ten at the Supreme Court.

The losses are the outliers, and so were the asks:

  • He claimed a 1977 emergency statute that never uses the word "tariff," "duty," "tax," or any other synonym for those words authorized him to tax nearly every good entering the country.
  • He asked the Court to read into the Fourteenth Amendment a limit on birthright citizenship that its text and 128 years of precedent foreclose.
  • He tried to fire a sitting Federal Reserve governor, Lisa Cook, without the process the law requires.
  • He sought to federalize the Illinois National Guard and send it into Chicago.
  • He deported Venezuelans under the Alien Enemies Act, a 1798 wartime statute, on roughly a day's notice.
  • He wanted the Postal Service to rewrite election rules less than two months before Election Day.

Despite the major weaknesses of the legal arguments supporting Trump’s positions in these cases, his justices rarely said no together. Kavanaugh would have upheld the tariffs. Gorsuch would have rejected the facial challenge to the birthright order and the objections to the Chicago Guard deployment. Gorsuch and Barrett would have let him fire a sitting Fed governor; that case went against Trump 5-4. Of his marquee losses, only the Postal Service rule, fifty days before an election, drew all three against him.

“Legends both”

To understand what the President clearly wants his appointees to be, look no further than Justices Clarence Thomas and Samuel Alito, whom the President calls “legends both.” In the mail-ballot case, U.S. Postal Service v. California, Alito dissented, joined only by Thomas.

Both justices market themselves as textualists, originalists and federalists. Yet they dropped all three methods the moment they got in Trump’s way. The Elections Clause says the rules for congressional elections "shall be prescribed in each State by the Legislature thereof," subject to modification by Congress. They would have allowed Trump to bypass that Clause entirely by invoking the Post Office's general authority to regulate the mail. Originalism? The Framers, fresh from a revolution against a concentrated executive, kept the executive out of running elections; Thomas and Alito would have handed the executive sweeping, unilateral power in the midterms. Federalism?  When the States told the Court, that in addition to its unconstitutionality, the overhaul was logistically impracticable, Justice Alito wrote, "I take that problem very seriously, but it is not enough to convince me to deny the application."

Eisenhower's "mistakes" gave the country a far more liberal Court than Eisenhower wanted. Trump's justices have given him immunity, CASA, Slaughter, the effective end of the Voting Rights Act, the TPS terminations, Kavanaugh stops, a ballroom, the end of affirmative action, the end of abortion rights, and roughly a .900 batting average. What they refused him was the power to tax by decree, to unmake citizenship by executive order, to fire a Fed governor at will, to send troops into Chicago, and to run the midterms through the Postal Service.

All the conservative justices favor a country run by Republicans instituting GOP policies. All but Thomas and Alito do not, however, favor an unlimited presidency completely independent from the two other branches. That line, which the Court is barely drawing, derives much more from institutional and personal self-interest than partisan disloyalty.   

The Supreme Court term that begins today is already full of important cases involving climate change, assault weapons, and the separation of church and state, among others. Given that the midterms will be long over by the end of the term, expect a virtual sweep for the President, with maybe an outlier here or there. Either way, Trump will complain.

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by Eric Segall and Guest Blogger James Sample, who is a Professor of Law at Hofstra University.

Professor Sample is on the Board of Advisors of Georgia State University's Emmet Bondurant Center for Constitutional Law, Practice, and Democracy. Professor Segall is the Executive Director of the Center.

This essay also appears at Who Decides Who Decides? where Professor Sample writes regularly.