How Chief Justice Roberts Shaped Trump’s Supreme Court Winning Streak

Last February, Chief Justice John G. Roberts Jr. sent his eight Supreme Court colleagues a confidential memo that radiated frustration and certainty.

Former President Donald J. Trump, seeking to retake the White House, had made a bold, last-ditch appeal to the justices. He wanted them to block his fast-approaching criminal trial on charges of attempting to overturn the 2020 election, arguing that he was protected by presidential immunity. Whatever move the court made could have lasting consequences for the next election, the scope of presidential power and the court’s own battered reputation.

The chief justice’s Feb. 22 memo, jump-starting the justices’ formal discussion on whether to hear the case, offered a scathing critique of a lower-court decision and a startling preview of how the high court would later rule, according to several people from the court who saw the document.

The chief justice tore into the appellate court opinion greenlighting Mr. Trump’s trial, calling it inadequate and poorly reasoned. On one key point, he complained, the lower court judges “failed to grapple with the most difficult questions altogether.” He wrote not only that the Supreme Court should take the case — which would stall the trial — but also how the justices should decide it.

“I think it likely that we will view the separation of powers analysis differently” from the appeals court, he wrote. In other words: grant Mr. Trump greater protection from prosecution.

In a momentous trio of Jan. 6-related cases last term, the court found itself more entangled in presidential politics than at any time since the 2000 election, even as it was contending with its own controversies related to that day. The chief justice responded by deploying his authority to steer rulings that benefited Mr. Trump, according to a New York Times examination that uncovered extensive new information about the court’s decision making.

This account draws on details from the justices’ private memos, documentation of the proceedings and interviews with court insiders, both conservative and liberal, who spoke on the condition of anonymity because deliberations are supposed to be kept secret.

The chief justice wrote the majority opinions in all three cases, including an unsigned one in March concluding that the former president could not be barred from election ballots in Colorado.

Another case involved a highly unusual switch. In April, the chief justice assigned Justice Samuel A. Alito Jr. to write a majority opinion saying that prosecutors had gone too far in bringing obstruction charges against some Capitol rioters. But in late May, the chief justice took it over.

Who initiated the change, and why, is not clear. The switch came days after The Times reported that an upside-down flag, a symbol of the Stop the Steal movement, had flown outside the Alito home following the Capitol attack. While that timing is suggestive, it is unclear whether the two are linked. (All nine justices declined to respond to written questions from The Times, a Supreme Court spokeswoman said.)

During the February discussions of the immunity case, the most consequential of the three, some of the conservative justices wanted to schedule it for the next term. That would have deferred oral arguments until October and almost certainly pushed a decision until after the election. But Chief Justice Roberts provided crucial support for hearing the historic case earlier, siding with the liberals.

Then he froze them out. After he circulated his draft opinion in June, Justice Sonia Sotomayor, the senior liberal, signaled a willingness to agree on some points in hopes of moderating the opinion, according to those familiar with the proceedings. Though the chief justice often favors consensus, he did not take the opening. As the court split 6 to 3, conservatives versus liberals, Justice Sotomayor started work on a five-alarm dissent warning of danger to democracy.

In his writings on the immunity case, the chief justice seemed confident that his arguments would soar above politics, persuade the public, and stand the test of time. His opinion cited “enduring principles,” quoted Alexander Hamilton’s endorsement of a vigorous presidency, and asserted it would be a mistake to dwell too much on Mr. Trump’s actions. “In a case like this one, focusing on ‘transient results’ may have profound consequences for the separation of powers and for the future of our Republic,” he wrote. “Our perspective must be more farsighted.”

But the public response to the decision, announced in July on the final day of the term, was nothing like what his lofty phrases seemed to anticipate.

Both conservatives and liberals saw it as an epic win for Mr. Trump. The former president and his supporters exulted over the decision, which greatly expanded presidential immunity and pushed off any trial until well after the election — if ever. To Democrats, the Republican-appointed justices were brushing away the violent Capitol attack and abandoning the core principle that no one is above the law. The chief justice, who had long said he wanted to keep the court out of politics, had plunged it more deeply in.

Now his opinion is the key document in a legal drama playing out this autumn, as the judge presiding over the long-delayed trial, Tanya S. Chutkan, parses what the court meant and how to move forward. Legal scholars say her job won’t be easy. Despite the chief justice’s reputation as a methodical craftsman, many experts, both conservative and liberal, say he produced a disjointed, tough-to-interpret opinion.

“It’s a strange, sprawling opinion,” said William Baude, a University of Chicago law professor and a former clerk to the chief justice. “It’s hard to tell what exactly it is trying to do.”

Others said the ruling was untethered from the law. “It’s certainly not really tied to the Constitution,” said Stephen R. McAllister, a law professor at University of Kansas and former clerk to Justice Clarence Thomas.

But inside the court, some members of the majority had complimented the chief justice even as they requested changes. Two days after the chief justice circulated his first draft in June, Justice Brett M. Kavanaugh responded to what he called an “extraordinary opinion.”

Soon afterward, Justice Neil M. Gorsuch added another superlative: “I join Brett in thanking you for your remarkable work.”

Roberts’s Unsigned Opinion

Two years earlier, as the other conservative justices overturned Roe v. Wade, the chief justice had been sidelined as he sought a middle ground that would restrict but not eliminate the constitutional right to abortion. In failing to persuade a single colleague to adopt his approach, he appeared to lose control of the court. This term he seemed determined to regain it.

In February, the justices heard arguments on a provocative question. The Constitution’s Fourteenth Amendment, adopted after the Civil War, contains language barring insurrectionists from holding office. So could Colorado kick Mr. Trump off the ballot in its Republican primary, creating an obstacle for his presidential campaign?

From the start of the justices’ private discussions of the case, Trump v. Anderson, it was clear that the court was going to say no, according to several people at the court familiar with the conversations. Allowing states to excise candidates from ballots in a national election was out of the question, the justices agreed. With sparse and cryptic text in the amendment, and little case law, to guide them, they raised various ideas for the court’s ruling and rationale.

The court’s conservative supermajority has prevailed in many of the most consequential cases in recent years. This time, Chief Justice Roberts told his colleagues he wanted the decision to be unanimous and unsigned. In any politically charged case, agreement among the justices made the decision more authoritative. He even said he would consult individually with everyone to discuss what they would accept — a rare step.

While all nine justices agreed that Mr. Trump should remain on state ballots, four of the conservatives were pushing to go beyond that and rule that the Constitution’s prohibition would require congressional action to take effect. Such a decision would provide greater protection for Mr. Trump: To prevent him from taking office if he won re-election, Congress would have to vote to enforce the insurrectionist ban.

That left the chief justice in control of the outcome. He lingered over the choice, those familiar with the process said. Ultimately, he sided with the four conservatives in an opinion that he wrote but that was issued unsigned. Justice Amy Coney Barrett and the three liberals wrote concurrences saying the majority had gone too far.

A Change of Authors

The next case, one with the potential to undermine charges against Mr. Trump, spurred behind-the-scenes footwork by the justices, including the mysterious reassignment of a majority opinion.

The case, Fischer v. United States, posed another sensitive question: Had prosecutors overreached in charging some Jan. 6 rioters under a law originally aimed at white-collar crime? Of the nearly 1,500 people who had been indicted in the Capitol attack as of June, when Fischer was decided, about 250 cases included a charge of obstructing an official proceeding.

After oral arguments in April, a majority of the court, including the chief justice, privately concluded that prosecutors had erred. It appeared that the result would narrow, overturn or prevent convictions of some Capitol rioters. It also seemed poised to imperil some of the charges against Mr. Trump, which included obstructing Congress’s certification of the 2020 election.

The chief justice assigned the opinion to Justice Alito, according to several court insiders. But a month later, Chief Justice Roberts updated the court: Justice Alito was no longer the author. The chief justice was taking over the opinion.

Outside the court, the switch went undetected. Inside, it caused surprise. To change authors without the judgment itself shifting was a break from court procedure, several court insiders said.

In interviews, Supreme Court scholars agreed. “Can I tell you an instance when it’s happened? No,” said Paul J. Wahlbeck, a professor at George Washington University who has studied opinion assignments.

The chief justice and Justice Alito did not respond to inquiries from The Times about the reason for the change. But the date of the new assignment, May 20, offers a possible clue. Four days earlier, The Times had reported on the upside-down flag that flew at the Alitos’ Virginia home soon after the Jan. 6 insurrection at the Capitol.

As the three Jan. 6 cases were being decided, Americans’ trust in the court was at a near low, polls show. Justice Thomas had declined to recuse himself from matters related to Jan. 6, even though his wife, Virginia Thomas, had encouraged Mr. Trump’s efforts to overturn the election. After the flag revelations, some legal experts and lawmakers pushed Justice Alito to recuse himself from the three cases. He also declined.

The change in authorship wasn’t the last shift in the case. Soon after, Justice Ketanji Brown Jackson deployed her vote to change the outcome.

As in the Colorado case, the vote did not fall along strictly partisan lines. Justice Barrett, along with Justices Sotomayor and Elena Kagan, felt that prosecutors were entitled to charge rioters under the obstruction law. It appeared that Justice Jackson would stand alone. She agreed with the majority that the law had been applied too broadly, according to several court insiders. But she thought the others were going too far by reversing the lower court’s judgment, tossing out the charge in the case before them and undermining many others.

Her intermediate position gave her leverage. She said she would join the majority if they would send the cases back to the lower courts to be reconsidered. The conservatives said yes. The final vote was 6 to 3, with Justice Barrett siding with the liberals and Justice Jackson with the conservatives.

Prosecutors would get a shot at salvaging some of the cases, including charges against Mr. Trump.

Former President Donald J. Trump, who on Jan. 6 encouraged supporters to go to the Capitol, was also indicted on charges including obstruction. Pete Marovich for The New York Times

Redefining Presidential Immunity

The immunity case, Trump v. United States, would determine whether and how the once and would-be future president could be prosecuted on charges of trying to overturn an election.

Just after the chief justice sent his Feb. 22 memo, showing that he was sympathetic to Mr. Trump’s arguments, his position became stronger. Justice Kavanaugh responded the next morning, agreeing with the chief’s logic, according to insiders who knew of the exchange. The three most conservative justices were presumably on board, and with two of the justices at the court’s ideological center in agreement, the direction was clear.

At the justices’ private conference meeting that day, Justice Sotomayor protested that she did not see how the court could reverse the appellate decision. It would look like the Supreme Court was being used to delay the trial, she said, according to someone with knowledge of the proceedings.

So she and the other liberal justices focused on the crucial question of timing. Every day that the court waited to hear the case was a benefit to Mr. Trump, diminishing the possibility of a trial before the Nov. 5 election. At the meeting, some of the court’s most conservative members said they did not want to hear the case until the start of the next term in October, according to several court insiders.

Justice Thomas, who favored scheduling the arguments in October, told colleagues that he did not want to see the court dragged into political battles.

Justice Gorsuch agreed. The matter was too important to rush, he said, and lawyers on the case would need time to prepare their strongest arguments.

On that schedule, the Supreme Court would not decide the immunity question until after the presidential contest. If Mr. Trump won, he could have the criminal case dismissed.

The decision in Trump v. United States set off a national uproar, granting sweeping immunity to the former president.

Once again, the chief justice’s position prevailed: He preferred to hear the case in the current term, and Justice Kavanaugh was amenable. Oral arguments were set for two months later. While relatively fast by the court’s usual standards, that timing frustrated many Democrats.

The justices instructed lawyers from both sides to address a broad question: “whether and if so to what extent does a former president enjoy presidential immunity from criminal prosecution for conduct alleged to involve official acts during his tenure.”

On April 25, the justices and the lawyers in the case gathered for oral arguments in the courtroom, across the street from where the Jan. 6 rioting had taken place three years earlier. The clamor from the Capitol attack had been audible from inside the court building, former employees recalled in interviews, and afterward, security sharply increased and fences shielded the building.

During the arguments, however, several conservative justices said that they wanted to focus not on what had happened that day, but on broader legal questions.

“I’m not discussing the particular facts of this case,” Justice Alito told the courtroom.

“I’m not focused on the here and now of this case,” Justice Kavanaugh said. “I’m very concerned about the future.”

“We’re writing a rule for the ages,” Justice Gorsuch said.

All of the conservative justices, including the three Trump appointees, had voted against Mr. Trump or his administration in some major cases. The chief justice, who had cast several crucial votes with liberals, had once taken the extraordinary step of rebuking Mr. Trump to defend the independence of the judiciary.

But the chief justice and Justice Kavanaugh had spent formative years as White House lawyers, working to protect presidential power. At oral arguments, Justice Kavanaugh and some other conservatives worried aloud that presidents without sufficient immunity might become overly cautious or vulnerable to politically motivated prosecutions.

Chief Justice Roberts, echoing his critique in the February memo, called the logic of the appeals court ruling circular. “As I read it, it says simply a former president can be prosecuted because he’s being prosecuted,” he said.

Two years ago, Chief Justice John G. Roberts Jr. appeared to have lost control of the court. This past term, he seemed intent on regaining it. Erin Schaff/The New York Times

When the justices met in private shortly after the arguments, the six conservatives voted in favor of Mr. Trump and greatly expanding presidential immunity. The three liberals voted against. After the chief justice circulated a draft on June 1, and Justice Sotomayor responded that she would consider a partial compromise, her invitation appeared to go nowhere.

That left the chief justice with plenty of requests for changes from members of his own majority, but only one main challenger: Justice Barrett. After he filed his draft majority opinion, she seemed somewhat skeptical, saying she intended to vote with him, but could not join on three points, according to people familiar with the discussions.

Inside the chief’s chambers, all four of his clerks participated in a furious rewriting effort. Later, others at the court wondered if the chief justice had taken on too much. The writing of a majority opinion requires responding to suggestions and edits from other justices, addressing any dissents, and crafting an analysis to withstand scrutiny. He had assigned himself seven majority opinions over the term, five of them blockbuster cases.

Months earlier, on the ballot case, the chief justice had sought consensus. But the immunity decision, which was issued on July 1 and set off a national uproar, reflected a court cleaved sharply in two.

The majority awarded sweeping immunity to Mr. Trump. The opinion did not say whether any of the crimes he had been accused of were fair game for prosecution, even though Mr. Trump’s lawyer had repeatedly conceded in oral arguments that some of the charges against his client appeared to concern purely private acts outside the role of president.

Chief Justice Roberts’s language in the opinion seemed intended to stay above the fray, extending protections to “all occupants of the Oval Office, regardless of politics, policy or party.” But in a withering dissent, Justice Sotomayor wrote that the majority opinion gave Mr. Trump “all the immunity he asked for and more.” It also, she wrote, protected “treasonous acts,” transformed the president into “a king above the law” and ultimately caused her to “fear for our democracy.”

The court’s leader shot back that the liberal justices “strike a tone of chilling doom that is wholly disproportionate to what the court actually does today.”

The immunity ruling proposed three categories of protection for former presidents accused of having committed crimes while in office: absolute immunity for core responsibilities set out in the Constitution, at least presumptive immunity for all other official conduct and no immunity for private acts that fall outside of presidential duties.

But many legal experts said they could not figure out how the ruling should be applied. Even Justice Barrett, who had joined much of the opinion, wrote that it could have been clearer.

One footnote left scholars wondering whether former presidents could ever be prosecuted for taking bribes. An N.Y.U. professor was startled to discover that the opinion, which leaned heavily on Nixon v. Fitzgerald, a 1982 case on presidential immunity, truncated a quote from that decision, changing its meaning.

Now one person above all others is charged with interpreting the decision in Trump v. United States: Judge Chutkan, who was presiding over the trial that stalled last winter when the chief justice sent his memo and the court took the case. Since then, Mr. Trump has been convicted of falsifying business records in New York, but the sentencing has been deferred until after the election, and three other efforts to prosecute him have, for now at least, run aground.

For the trial before Judge Chutkan to resume, she must examine the indictment, which prosecutors reframed after the Supreme Court ruling, and decide which charges against Mr. Trump can survive.

Both sides will be able to appeal her interpretation of the new immunity rules. More delay is likely to ensue. Her conclusions could be sent up to the appellate court in Washington. And then the very same question, of just how accountable Mr. Trump can be held for trying to overturn an election, will likely return to the nine justices on the Supreme Court.

Alan Feuer contributed reporting, and Julie Tate contributed research.

Jodi Kantor is a Times investigative reporter and co-author of “She Said,” which recounts how she and Megan Twohey broke the story of sexual abuse allegations against Harvey Weinstein. More about Jodi Kantor

Adam Liptak covers the Supreme Court and writes Sidebar, a column on legal developments. A graduate of Yale Law School, he practiced law for 14 years before joining The Times in 2002.

How Roberts Shaped Trump’s Supreme Court Winning Streak

Behind the scenes, the chief justice molded three momentous Jan. 6 and election cases that helped determine the former president’s fate.

Roberts’s Unsigned Opinion

A Change of Authors

Redefining Presidential Immunity