With potential retirements looming, Trump eyes lasting imprint on Supreme Court, experts say
Having managed to become only the second person to be elected to non-consecutive terms, alongside Grover Cleveland, President Donald Trump has an opportunity to hand-pick an ideological majority on the Supreme Court.
President Donald Trump nominated three Supreme Court justices for appointment during his first term in the span of just three years.
Most presidents fill one, occasionally two, Supreme Court seats during a four-year term. So Trump’s three successful nominations — replacing Justices Antonin Scalia and Ruth Bader Ginsburg after their deaths, and Justice Anthony Kennedy following his retirement — made an unusually consequential single term.
Now, having managed to become only the second person to be elected to non-consecutive terms, alongside Grover Cleveland, who was the 22nd and 24th U.S. president and successfully appointed four justices to the Supreme Court, Trump has an opportunity to hand-pick an ideological majority that could continue to define the court for decades to come, experts say.
Though there is still much to play out over the next few years, experts say it is possible that Justices Clarence Thomas and Samuel Alito — ages 77 and 76, respectively — retire or leave the court during Trump’s second term. Organizations such as the progressive advocacy group Demand Justice have already begun organizing a campaign to block any potential nominees, even though neither justice has shared plans to retire.
If Alito and Thomas were to retire, the resulting supermajority — if Trump once again had successful nominations to the court — could cement for generations how the Constitution is applied to major questions, including on voting and elections, environmental policy, the administrative state and many other aspects of public life, experts say.
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After the high court rebuffed Trump in February by striking down his use of emergency powers to implement tariffs on foreign countries, the president was questioned about whether he wanted Thomas or Alito — the two conservative justices who ruled in his favor in the case — to retire. Fresh off the defeat and visibly irked by the outcome, Trump said during a press conference at the White House that he hoped the two justices “stay healthy” and remain on the court.
But asked last month in a conversation with Maria Bartiromo of Fox News about his plan for the court should vacancies arise, Trump suggested that he is prepared to appoint up to three justices. Republican Sen. Chuck Grassley, of Iowa, who chairs the Senate Judiciary Committee, the body tasked with vetting judicial nominations, likewise signaled a readiness to speedily process potential candidates to the court before the November midterms.
The last president to seat five justices, back in the 1950s, was former President Dwight D. Eisenhower. Before that, William Howard Taft, the 21st president, seated five justices and elevated one to chief justice in the early 1900s. Before Taft, the last president to appoint at least five justices was Ulysses S. Grant, who served consecutive presidential terms from 1869 to 1877.
Talk of potential retirements kicked up in the wake of the tariff decision as Alito gears up for an October book launch a day after the Supreme Court’s next term is set to begin, according to Hachette Book Group, his publisher. Alito was also hospitalized last month after he fell ill during a dinner, but he has since returned to the bench. It also comes as Thomas marks an extraordinary milestone on the court: this week, he became the second-longest-serving Supreme Court Justice in history with more than 34 years of service.
Vacancies are all but inevitable, experts say, and increasingly the decisions of when to retire and how to fill seats reflect a shift in approach that has been decades in the making. Those decisions have moved away from an emphasis on serving on the bench until justices are more or less incapacitated, a shift that one legal commentator described as “strategic career-management.”
Jeremy R. Paul, a professor of law and former dean of the Northeastern University School of Law, argued that Trump has strong incentives to remain invested in the shaping of the court — even beyond key Republican policy issues.
In 2024, the Supreme Court ruled that former presidents are entitled to immunity from criminal prosecution for actions taken within the scope of their official duties. It was a major decision, Paul said, that significantly expanded the legal protections afforded to a sitting executive, and especially for Trump, who has faced multiple criminal indictments in recent years.
But the court stopped short of clearly defining what constitutes an “official” versus “unofficial” act, leaving that distinction to be worked out in lower courts — and in the future, likely after Trump leaves office and would potentially need to invoke those protections.
“The more people he has on the court that he has picked, the more likely they are to give ‘official acts’ a broad definition,” Paul said.
Trump’s shaping of the court
Retirement intrigue intensifies when a justice reaches an advanced age at the same time as an ideologically aligned president sits in the Oval Office, according to Dan Urman, director of the law and public policy minor at Northeastern University, who teaches courses on the Supreme Court. But Urman noted that ideological kinship has not always tracked neatly.
Justice David Souter, for example, was appointed by Republican President George H. W. Bush but later aligned with the court’s liberal wing, ultimately choosing to retire during Barack Obama’s presidency. Justice John Paul Stevens, appointed by Republican President Gerald Ford, likewise retired during the Obama years and was widely viewed as a leading member of the court’s liberal bloc.
“However, since 2010, when Elena Kagan was confirmed, the political party nominating a justice has served as a shorthand for the justices’ ideology,” Urman said.
Trump’s behind-the-scenes efforts at doing this during his first term are well-documented. There was a concerted pressure campaign to persuade Anthony Kennedy, a conservative jurist who often served as the swing vote, to retire. Trump dangled the possibility of replacing Kennedy with one of his law clerks, which ultimately led to the dramatic 2018 confirmation of Brett Kavanaugh.
Kennedy’s retirement cleared the way for a dramatic shift, replacing a pivotal swing vote who at times tempered the court on major decisions with a reliably conservative one, Urman said. Kavanaugh, who clerked for Kennedy in the early ‘90s, has taken a more conservative approach to constitutional interpretation than his predecessor.
In a way, the appointment of former clerks provides incentive for retiring justices to help anchor their judicial ideology when they’re no longer on the court, Urman and Paul said. “And both Alito and Thomas — and Thomas, in particular — have plenty of law clerks poised to become the next Supreme Court justice,” Paul said. “It would not be at all surprising to see him go to either or both of them and promise them that if they resign now, he’ll name one of their clerks as the successor.”
Kavanaugh’s confirmation was followed in 2020 by Amy Coney Barrett’s, after the death of liberal justice Ruth Bader Ginsburg. And, like those who preceded her, Barrett had clerked for former Justice Antonin Scalia.
Barrett’s confirmation capped Trump’s run of three successful appointments and cemented a conservative bloc that seemed expressly designed to secure wins on a host of Republican-backed legal priorities, including abortion restrictions, expanded gun rights and limits on federal regulatory power, Urman and Paul said.
And that bloc could expand its reach even further if Trump secures additional appointments, with experts pointing to administrative law doctrines, environmental regulations and voting rights protections as key areas likely to face further narrowing or reversal into the foreseeable future. Last week, the Supreme Court ruled along party lines that Louisiana’s redrawn congressional map, which includes two majority-Black districts, was an unconstitutional racial gerrymander in what critics of the decision described as a major blow to the Voting Rights Act.
Proponents of these changes frame them as a long-overdue realignment of the court with constitutional originalism, or the idea that cases should be decided on the basis of the Constitution’s original meaning at the time it was adopted. They, alongside their conservative champions on the court, say that individual states should have the right to decide on many of those issues rather than one single “court of last resort.”
Thomas, widely thought of as the court’s staunchest originalist, and Alito have criticized the more expansive readings of the founding document espoused by proponents of a so-called “living Constitution,” which has helped enshrine abortion rights, same-sex marriage and doctrines such as affirmative action in higher education.
Critics, however, warn that a durable conservative majority could dismantle some of those long-standing precedents and materially narrow the authority of federal agencies, curtailing civil liberties while limiting the federal government’s ability to rein in issues such as climate change, workplace safety and consumer protection. Equally concerning, according to critics, is the present court’s willingness to overturn precedent, or the idea that courts should generally adhere to past rulings to preserve stability in the law.
“The situation with regard to precedent now is troubling,” said Martha F. Davis, university distinguished professor of law. “Even if the court manages to become more ideologically balanced in terms of the membership, you don’t have stability in terms of the doctrine. If Trump gets to install more members, including justices who might be loyal to him — the problem will only worsen.”
The role of politics
A president’s second term in office often elicits the label of a lame duck, which refers to an executive whose political leverage wanes as allies and adversaries alike begin looking ahead to the next administration — and key elections leading up to it.
However, some indications suggest that Trump intends to be anything but a lame duck.
His administration, with the backing of a GOP-controlled Senate, has also been moving quickly to fill vacancies in the federal court system, experts say. Many of Trump’s 37 appointments on the federal bench have steered around the fact, or otherwise refused to outright state, that Joe Biden won the 2020 election for president, suggesting an unusually high degree of ideological compliance with an administration in power, experts say.
“Trump has been very active in filling the Courts of Appeals, in particular, but also the district courts with very right-wing judges,” Davis said. “We have every reason to think that he’s thinking strategically about the [Supreme Court] again.”
Davis sees a number of factors that might be guiding the timing of a potential Alito or Thomas departure from the court. For one, she said the practice of “hanging on” rather than retiring when the political conditions are favorable can backfire, citing the “spectre of Ginsburg,” who was 87 and was battling pancreatic cancer when she died. Ginsburg’s death, Davis said, ultimately contributed to a “dramatic shift on the court.”
The 2026 midterms may also play a large role in how developments on the court play out over the remainder of Trump’s second term, the experts said. The Senate confirms justices by a simple majority vote and if Republicans were to lose control of that chamber, it could significantly change the calculus for Alito and Thomas. Both justices have indicated that they intend to occupy their seats at least through 2026.
Still, Davis said, retirement can’t be far from their minds.
“Both of them have to be thinking about it,” she said. “The problem is, if they were going to do that, they’d want to get it rolling before the election, before we know who’s going to control the Senate.”
At the end of the day, and despite Thomas’ repeated insistence that he plans to die on the bench, the pressures to ensure ideological continuity at a moment of generational polarization could force the two to step aside, the experts said. “On the one hand, [the justices] are living their best lives and generally seeing their constitutional vision implemented on the court,” said Urman. “On the other hand, they would like to hand over their position to someone who shares their ideology.”
