As the U.S. Supreme Court commences its 2025–26 term, Chief Justice John Roberts enters his third decade at the helm, facing perhaps the most consequential and turbulent period in the Court’s modern history. President Donald Trump, newly re-elected for a second term, stands at the center of a series of legal and constitutional battles, with the Supreme Court frequently called upon to weigh in on sweeping executive actions and the boundaries of presidential authority.

Roberts, appointed in 2005 by President George W. Bush, has seen the Court’s ideological landscape shift dramatically over two decades. Now, at age 70, his influence and judicial philosophy of institutional restraint are under renewed scrutiny as critics argue the Court is failing to check the expansion of executive power wielded by a norm-breaking White House.

Mounting Executive Power and the Supreme Court’s Response

President Trump’s second administration has ushered in a wave of aggressive executive actions: targeting political adversaries for criminal prosecution, sweeping federal workforce cuts, and pressuring universities via funding controls. Last week’s 20-year anniversary of Roberts’ leadership was marked not just by reflection but by urgent debate on the Court’s modern role.

Many observers note that, in the opening months of Trump’s return to office, his administration has prevailed in 21 out of 25 emergency appeals to the high court—decisions often rendered without full briefing or oral arguments, a process known as the “shadow docket.” These expedited and frequently unexplained judgments have drawn sharp criticism for their lack of transparency and for muddying legal precedents for lower courts.

“They’re making, in essence, merits decisions and not explaining them for the public, not explaining them to lower-court judges,” noted longtime political reform advocate Fred Wertheimer.

Some lower court judges have expressed frustration with the Supreme Court’s methods, warning that brief, precedent-setting decisions leave them with little guidance and undermine public trust in the judiciary.

Presidential Immunity Ruling and Its Ripple Effects

Tensions peaked with the Supreme Court’s July 2024 ruling, written by Roberts himself, which greatly expanded the scope of presidential immunity for official acts. The case stemmed from Trump’s prosecution for alleged efforts to overturn the 2020 election results. Roberts’ opinion held that former presidents are broadly immune from criminal liability tied to their official functions—a determination that supporters called vital for executive independence, but that critics decried as a shield for potential lawbreaking.

Trump swiftly seized on the decision, publicly asserting a sweeping sense of legal invulnerability that has influenced policy and public perception. Congressional Democrats and legal scholars have charged that the Court’s action has emboldened further executive overreach, potentially undermining core democratic institutions.

“The Supreme Court and the chief justice have given Americans zero reason to believe that they will slow this president in any way whatsoever,” commented former appellate judge J. Michael Luttig.

However, some analysts suggest Roberts may have intended the ruling to quiet escalating partisan legal battles, possibly anticipating a different election outcome last year. Still, the precedent now stands as a defining moment in the doctrine of presidential accountability.

Checking Executive Overreach: Limited, Yet Meaningful, Pushback

While the Court has often sided with Trump’s administration, Roberts’ leadership has not been without moments of restraint. This year, the Court intervened to halt broad deportations under the Alien Enemies Act and required due process for targeted Venezuelan migrants, insisting that the administration provide notice and legal access prior to removal—though such decisions often followed government actions that skirted lower-court orders.

In another emergency-docket case, Roberts opposed the administration’s bid to cut $65 million in education grants from blue states, signaling, if quietly, a reluctance to endorse every executive maneuver.

Historically, Roberts shaped critical 5–4 majorities that checked Trump’s ambitions, as in the 2020 DACA case allowing Dreamers to remain in the U.S., and the 2019 ruling blocking a citizenship question on the census. But with the Court’s post-Ginsburg 6–3 conservative supermajority, Roberts’ centrality as a swing vote has diminished, making it harder to steer outcomes toward moderation or incremental change.

The Shadow Docket: Speed Versus Transparency

The Court’s growing reliance on the shadow docket for high-stakes, emergency decisions has amplified debate about judicial transparency. In fiscal year 2025, the number of shadow-docket rulings on significant national policies hit an all-time high. Critics from the bench and bar warn that scant opinions and late-night orders risk damaging the public’s faith in judicial impartiality.

“I analogize the shadow docket to, essentially, rulings on the back of a napkin,” said former federal judge Nancy Gertner.

Nevertheless, some Supreme Court practitioners argue that Roberts’ reluctance to elaborate in such cases reflects a mainstream judicial philosophy: emergency appeals often come before full factual development and should not lock the Court into premature precedents.

Roberts’ Judicial Minimalism Tested

John Roberts began his tenure as chief justice with a philosophy of “judicial minimalism”—the idea that courts should decide no more than absolutely necessary. “If it’s not necessary to decide more to dispose of a case, then, in my view, it is necessary not to decide more,” he famously told the Senate in 2005.

Yet, the current era of deep polarization and relentless confrontation between branches of government has rendered that approach increasingly difficult. The Court is now regularly thrust into disputes over far-reaching constitutional questions, from abortion and gun rights to presidential powers and the future of America’s regulatory state.

This dynamic partially explains why, even as Roberts has sometimes tried to cool institutional rhetoric and slow the pace of legal change, his tenure has also witnessed some of the Court’s most transformative and controversial rulings in decades, including the overturning of Roe v. Wade in 2022, expanding Second Amendment rights, and drastically revising the rules for affirmative action.

Outlook: The Supreme Court at a Crossroads

As another term begins, the Supreme Court faces a docket packed with Trump-related cases: the scope of presidential power over federal agencies, the limits of economic sanctions and tariffs, challenges to regulatory independence, and expected appeals involving free speech, voting rights, and the separation of powers. Legal scholars and lawmakers across the spectrum are calling on the Court, and Roberts in particular, to provide clarity and principled checks as the boundaries of executive authority are redrawn in real time.

Roberts’ influence and the Court’s role as a backstop of constitutional order may be tested further in the coming months and years. What is clear: The decisions handed down under his continued leadership will shape the contours of American democracy for generations to come.