The gavel falls, and another executive order hits the skids. Federal judges, cloaked in black robes and armed with injunctions, have become the bane of President Donald Trump’s second term, much like they were for President Franklin D. Roosevelt nearly a century ago.
But Trump is involved in an important fight over the legitimate powers of the federal judiciary and his own under Article II of the Constitution. The outcome will have major implications for the constitutional separation of powers that go far beyond whether Trump is able to implement his preferred policies.
Since Trump returned to the White House in January, his agenda — slashing federal agencies, curbing immigration, and empowering the Department of Government Efficiency under Elon Musk — has collided head-on with the federal judiciary. The clashes began almost immediately. On Feb. 4, a federal judge in New York blocked DOGE’s access to Treasury payment systems, citing privacy concerns raised by 19 state attorneys general. Days later, judges in New Hampshire, Washington, and Maryland halted Trump’s executive order attempting to end birthright citizenship, a cornerstone of his immigration crackdown. By mid-April, the Congressional Research Service tallied 17 Trump policies blocked by federal courts, a pace that dwarfs the judicial resistance faced by the last two Democratic presidents.
The pattern is familiar: Trump acts, opponents sue, and a judge, often appointed by a Democratic predecessor, issues a nationwide injunction. Trump’s response? A mix of defiance and social media broadsides. In March, he suggested the administration might ignore a court order to halt deportations of alleged Venezuelan gang members, posting, “He who saves his Country does not violate any Law.” Vice President JD Vance chimed in, questioning whether judges can “control the executive’s legitimate power.” Even Chief Justice John Roberts, typically reserved, felt compelled to push back, issuing a rare statement criticizing Trump’s calls to impeach judges who rule against him.
The Supreme Court, with its 6-3 Republican-appointed majority, has been cautious, avoiding direct confrontation. In April, it ruled against Trump’s attempt to freeze $2 billion in foreign aid, splitting 5-4, and sidestepped the merits of a Venezuelan migrant case by citing procedural errors. These narrow, technical rulings suggest the justices are wary of a showdown with a president who thrives on challenging institutional legitimacy. Yet the lower courts, emboldened by a lack of congressional pushback, remain the primary battleground. With Republicans controlling Congress, the judiciary is the last line of defense for Trump’s opponents, leaving the courts as the only check on his ambitions.
Looking ahead, the legal gauntlet shows no signs of easing. Trump’s push for mass deportations, including a plan to target 425,000 migrants with prior removal orders, faces lawsuits from immigrant advocacy groups and blue-state governors. His impoundment efforts, withholding congressionally authorized funds to starve agencies such as the U.S. Agency for International Development, have drawn fire from Democrats and even some GOP senators wary of executive overreach. DOGE’s mission to fire tens of thousands of federal employees and Trump’s attempt to wind down the Department of Education are mired in litigation over civil service protections and congressional authority. And looming on the horizon is a possible Supreme Court battle over nationwide injunctions, which critics argue give individual judges outsize power to derail executive action undertaken by a nationally elected president.
For Trump, the stakes are monumental. His supporters see him as a wrecking ball to the deep state, fulfilling a mandate to shrink government and restore national sovereignty. Every judicial block fuels their narrative of an elitist system thwarting the will of the people. But the courts aren’t just a nuisance. They’re a structural barrier, rooted in the Constitution’s checks and balances, that could stall Trump’s revolution unless he navigates them shrewdly.
Enter Franklin D. Roosevelt, a president who faced a similar judicial wall and, through a mix of audacity and adaptation, found a way through. In 1932, Roosevelt swept into office promising a “New Deal” to lift America from the Great Depression’s depths. His first term saw a flurry of legislation — banking reforms, public works, agricultural subsidies, and labor protections — designed to stabilize the economy and empower the federal government. But the Supreme Court, dominated by conservative justices dubbed the “Four Horsemen,” had other ideas. Between 1934 and 1936, the court struck down key New Deal programs, including the National Industrial Recovery Act and the Agricultural Adjustment Act, as unconstitutional overreaches.
Roosevelt, fresh off a 1936 landslide, wasn’t about to let nine unelected justices derail his vision. In February 1937, he unveiled the Judicial Procedures Reform Bill, a brazen plan to “pack” the Supreme Court by adding one justice for every sitting justice over 70, up to a maximum of six. The pitch was couched in practical terms — older justices needed help with caseloads — but no one was fooled. Roosevelt wanted to stack the court with liberals who would greenlight his agenda.
The backlash was swift. Newspapers decried Roosevelt as a dictator-in-waiting. The American Bar Association, with 86% of its members opposed, joined a coalition of civil libertarians and corporate lawyers to tank the bill. Even Democrats, including Senate Judiciary Committee leaders, rebelled, issuing a scathing report calling the plan “an invasion of judicial power.” By July 1937, after 168 days of debate, the bill was dead.
Even as Roosevelt lost the court-packing battle, he won the war. In the spring of 1937, the Supreme Court began upholding New Deal laws, including the National Labor Relations Act and the Social Security Act. Historians call it “the switch in time that saved nine,” attributing the shift to Justice Owen Roberts, who flipped to the liberal side. Some argue Roberts was swayed by Roosevelt’s pressure. Others say he was already leaning that way. Either way, the court’s pivot legitimized a vast expansion of federal power, cementing Roosevelt’s legacy. Over his 12 years in office, Roosevelt appointed eight justices, reshaping the judiciary without ever passing his controversial bill.
Former President Joe Biden and many congressional Democrats hatched their own court-packing scheme to thwart the current Republican-appointed majority. But one needn’t support these constitutionally dubious plans to see how Trump can fight his own political battles against federal judges testing the limits of their power.
Like Roosevelt, Trump faces a judiciary skeptical of his transformative vision. Like Roosevelt, he is backed by a popular mandate and a compliant Congress yet stymied by judges wielding constitutional vetoes. And like Roosevelt, Trump’s rhetoric, blasting “activist” judges and hinting at defiance, risks alienating the very institution he needs to advance his agenda.
But conservatives, of course, aren’t exactly FDR fans. His New Deal laid the groundwork for the sprawling federal bureaucracy that Trump is attempting to dismantle. His court-packing scheme, to many on the Right, was a power grab that flirted with authoritarianism. So, what can Trump learn from a president whose legacy is anathema to conservative principles? The answer lies not in Roosevelt’s ends but in his means — his ability to adapt, pressure, and outlast his opponents.
Trump’s public attacks on judges, while crude, keep the judiciary on notice. His base loves it, and it signals to the courts that defiance comes with political costs. The Supreme Court’s Republican-appointed majority, already sympathetic to executive power, may hesitate to kneecap Trump’s agenda if public support holds. But Trump must tread carefully. He risks alienating a judiciary with lifetime appointments that could outlast his term.
In Roosevelt’s case, time was on his side. Retirements and deaths allowed him to appoint justices who shared his vision. Trump, at 78, won’t serve 12 years, but his first term already delivered three Supreme Court justices, tilting the balance rightward. If Justices Sonia Sotomayor or Elena Kagan retire, Trump could cement a 7-2 conservative supermajority. Lower court appointments, too, will shape the judicial landscape for decades. Trump’s team should prioritize filling vacancies with judges who share his deregulatory zeal, ensuring long-term wins even if short-term battles falter.
As the Supreme Court eventually met Roosevelt halfway, upholding New Deal laws without requiring a constitutional overhaul, Trump could seek a similar detente. For instance, scaling back DOGE’s most legally vulnerable plans, such as firing protected civil servants en masse, could blunt judicial resistance while preserving core reforms. On immigration, narrower executive orders targeting specific criminal populations might survive scrutiny better than blanket measures. Compromise isn’t weakness. It’s a prudent strategy that Trump can use to keep the bigger fight alive.
Roosevelt’s court-packing plan flopped because the public, despite supporting the New Deal, revered the Supreme Court’s independence. Trump’s defiance resonates with his base, but new research shows that Americans, including many Republicans, still back checks and balances. To sustain his momentum, Trump must frame his battle as one against judicial overreach, not the rule of law itself. His gift for narrative, honed on social media and at rallies, can rally voters to pressure Congress and the courts, much as Roosevelt leveraged his fireside chats.
For conservatives, these lessons come with a caveat: Roosevelt’s victory expanded government in ways that clash with Trump’s mission. His judicial triumphs entrenched a regulatory state that conservatives have fought for generations. Trump’s challenge is to apply Roosevelt’s tactical savvy — pressure, patience, compromise, and public persuasion — without embracing his statist goals. The Constitution’s checks, which frustrated Roosevelt and now vex Trump, are a feature, not a bug, designed to prevent any one branch from steamrolling the others.
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Trump’s clashes with the courts are more than legal skirmishes. They’re a test of whether a determined president can reshape a system rigged to resist change. Roosevelt proved it’s possible, not by bulldozing the judiciary but by outmaneuvering it. Trump, with his knack for disruption, can follow suit — not by emulating Roosevelt’s policies but by borrowing his playbook. In the process, he can tear down the administrative state Roosevelt built.
The courts may slow Trump down, but history shows they won’t stop him. For a president who thrives on defying the odds, that’s a challenge worth relishing.
Daniel Ross Goodman is a Washington Examiner contributing writer and the author, most recently, of Soloveitchik’s Children: Irving Greenberg, David Hartman, Jonathan Sacks, and the Future of Jewish Theology in America.