Most legal experts say that former President Donald J. Trump will face deep skepticism at the Supreme Court on Thursday, when the justices will hear arguments on his claim that he is absolutely immune from prosecution on charges of plotting to subvert the 2020 election.
Mr. Trump would prefer to win, of course. But there are, from his perspective, at least two attractive ways to lose.
One involves the timing of the court’s decision, which has received substantial attention given the relatively leisurely pace it has set for itself in the case. Even if Mr. Trump eventually and categorically loses, each passing week makes it more challenging for Jack Smith, the special counsel in the case, to complete the trial before the election.
The other, which has received less consideration but is no less important, is the possibility that the court’s ruling, even if issued promptly, will inject additional legal complications into the case that will take time to sort out.
That is what happened in 2020, when another case involving Mr. Trump reached the justices just months before a presidential election. The question was similar to the one the court will consider on Thursday: whether Mr. Trump was entitled to a form of absolute presidential immunity allowing him to block prosecutors from obtaining his tax records.
In July 2020, Mr. Trump lost the case. But the loss was a kind of victory. The court sent the case back to the lower courts for more analysis, running out the clock.
In a concurring opinion, two of Mr. Trump’s appointees — Justice Brett M. Kavanaugh, joined by Justice Neil M. Gorsuch — summarized the court’s mixed message this way: “The court today unanimously concludes that a president does not possess absolute immunity from a state criminal subpoena, but also unanimously agrees that this case should be remanded to the district court, where the president may raise constitutional and legal objections to the subpoena as appropriate.”
That turned out to be a good way to lose. The case kicked around for more than six months before returning to the Supreme Court in February 2021, when the justices issued a final ruling against Mr. Trump — months after the election.
In the case it will hear on Thursday, the Supreme Court could easily follow that approach, ruling against Mr. Trump but ordering lower courts to address other issues. Indeed, if the court is inclined to let judicial history repeat itself, the sentence from Justice Kavanaugh’s 2020 concurrence would need only a very light edit.
Norman Eisen, who served as special counsel to the House Judiciary Committee during Mr. Trump’s first impeachment, described what such a decision might say: “Of course there’s no absolute immunity. But here’s the test for the kind of immunity there is. And we are remanding for further proceedings consistent with this opinion.”
That outcome, Mr. Eisen said, “is a good loss for Trump, because that then gives him a vehicle to attempt to achieve more delay.”
The Supreme Court issued its decision in the 2020 immunity case on the last day of its term, July 9, about two months after it heard arguments. If the court follows a similar timeline in the new case, its decision would land in late June.
When Judge Tanya S. Chutkan suspended pretrial proceedings as appeals on the immunity question moved forward, her schedule contemplated that the parties would need some three months to prepare once the case returned to her court. That would suggest a trial date around Oct. 1, with the trial itself extending past the election and perhaps into 2025.
That timeline, though, assumes the Supreme Court will hand Mr. Trump a straightforward loss.
But there are reasons to think the court may be poised to issue a ruling that makes matters more complicated. Consider the question the court agreed to decide: “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 in office.”
Packed into that sentence are at least two potential distinctions: “to what extent” immunity may be available and whether the conduct in question is official or not. It is entirely conceivable that the Supreme Court’s ruling will instruct lower courts to do more work in analyzing those questions.
“If the court orders additional proceedings in the district court, holding trial before the election will become virtually impossible,” said a brief supporting Mr. Smith from Common Cause, a watchdog group.
But such a decision is well within the realm of possibility. It could have one or both of two main elements.
The court could reject absolute immunity but grant Mr. Trump a more limited form of protection like the qualified immunity that can apply to other government officials. If it does that, it could also well leave it to lower courts to sort out the contours of what that means.
Mr. Smith acknowledged that possibility but said it should not get in the way of a prompt trial. “Even if this court holds that a former president is entitled to some immunity from criminal prosecution for official acts,” he wrote, “that principle does not preclude trial on this indictment.”
The second distinction is that the justices could order lower courts to explore whether Mr. Trump’s conduct was part of his official duties.
In Nixon v. Fitzgerald in 1982, the Supreme Court ruled that former President Richard M. Nixon could not be sued by an Air Force analyst who said he was fired in 1970 in retaliation for his criticism of cost overruns.
“In view of the special nature of the president’s constitutional office and functions,” Justice Lewis F. Powell Jr. wrote for the majority in the 5-to-4 ruling, “we think it appropriate to recognize absolute presidential immunity from damages liability for acts within the ‘outer perimeter’ of his official responsibility.”
Mr. Smith argues that the precedent, arising from a lawsuit seeking money, does not apply to criminal cases. But he does not dispute that significant parts of his prosecution are based on conduct that might well satisfy the Fitzgerald standard if it applied.
Indeed, his main argument is that “a former president lacks absolute immunity from federal criminal prosecution for conduct involving his official acts.”
The Supreme Court could reject that argument and adopt a backup proposed by Mr. Smith: “Even if the court were inclined to recognize some immunity for a former president’s official acts,” he wrote, “it should remand for trial because the indictment alleges substantial private conduct in service of petitioner’s private aim.”
That would require Judge Chutkan to make fine distinctions in evidentiary rulings and jury instructions between official and unofficial conduct. Mr. Smith said such rulings should not be subject to immediate appeal, as immunity rulings generally are. Mr. Trump “can seek appellate review, if necessary, after final judgment,” Mr. Smith wrote.
But history suggests that Mr. Trump would try.
After his Supreme Court loss in 2020, Mr. Trump argued in lower courts that the subpoena at issue was overly broad and amounted to political harassment. After those arguments were rejected by a trial judge and the federal appeals court in New York, Mr. Trump returned to the Supreme Court, which rejected his application for emergency relief without comment.
New York prosecutors finally obtained the documents in February 2021, and information from them became part of the investigation that culminated in the hush-money case underway in Manhattan — almost four years after the Supreme Court ruled.
