For President Trump, next week’s election could be a moment where two roads diverge — one leads to the White House, and the other, possibly, to the big house. 

As the 45th president’s contest with Vice President Harris appears set to conclude in a photographic finish, the criminal cases against Trump are chugging along toward trial. The months of November and December are marbled with litigation deadlines. The most important one of all, though, is January 20.  

That’s when Trump could either raise his hand for the oath of office and assume the protections of the presidency — the Department of Justice forbids prosecuting sitting presidents — or stew at Mar-a-Lago while contemplating a protracted trial calendar that might not terminate in acquittals. If he loses, he also forfeits the ability to fire Special Counsel Jack Smith and dismiss the January 6 and Mar-a-Lago cases. 

Regardless of whether Trump wins on Tuesday, Judge Juan Merchan at New York on November 26 is set to hand down Trump’s sentence in the hush money case involving the attorney Michael Cohen and the adult film star Stephanie Clifford, known as Stormy Daniels.

On November 12, Judge Merchan is set to decide whether the Supreme Court’s landmark immunity ruling in Trump v. United States can protect Trump from the 34 state convictions secured against the former president by District Attorney Alvin Bragg. Mr. Bragg contends that the Nine’s decision “has nothing to say” about the “guilty” verdicts he secured. Judge Merchan’s prior rulings have overwhelmingly favored the state.

State crimes lie beyond the reach of the Department of Justice and the presidential pardon power, which covers only “Offenses against the United States.” That means that if Trump is sentenced to prison, that ruling will hold even if Trump wins the White House. He would likely appeal such a sentence to the Appellate Division, First Department, New York’s initial appellate tribunal. He would not report to prison until the appellate process is exhausted. Governor Hochul has suggested that a pardon is off the table.

If Trump wins and is sentenced to prison, the Supreme Court could intervene and stay the sentence for the pendency of his presidency. While the high court generally leaves state law to state courts, the Constitution’s Supremacy Clause ordains that “the Laws of the United States … shall be the supreme Law of the Land; and the Judges in every State shall be bound thereby.”

The justices in Trump showed special solicitude to presidential prerogative, quoting Alexander Hamilton for the proposition that “The Framers designed the Presidency to provide for a ‘vigorous’ and ‘energetic’ Executive.” The majority opinion warns against anything that would make the president “unduly cautious in the discharge of his official duties.” Reporting to prison would appear to pose an impediment to the exercise of the office of the president.

If Trump loses, he will  be deprived of levers to squash Mr. Smith’s prosecutions. While both the secret documents case and the election interference prosecution have been dealt delays, the special counsel has a path forward in both — but only if the 45th president does not become the 47th. The road to trial is more arduous in the Mar-a-Lago case, where the charges have been dismissed by Judge Aileen Cannon. She found that Attorney General Garland’s appointment of Mr. Smith was unlawful and ultra vires. 

Mr. Smith has appealed that ruling to the 11th United States Appeals Circuit, which could uphold Judge Cannon’s stunning ruling, overturn it, or even reassign her from the case if it finds that her stewardship of the documents matter has been tainted by the presence of perception of partiality. Many legal observers reckoned that this was the strongest of the four cases arrayed against Trump, and its charges drawn from Espionage Act and obstruction statutes carry the possibility of decades behind bars. 

While Mr. Smith’s prosecution of Trump for January 6 was upended by the Supreme Court’s ruling that official presidential acts are presumptively immune — and some enjoy “absolute” immunity — it has found new momentum in the courtroom of Judge Tanya Chutkan, whose rulings have been wholly adverse to Trump and to January 6 protesters. She allowed the special counsel to submit a book-length immunity brief arguing that Trump “must stand trial for his private crimes as would any other citizen.”

One of the charges levied by the special counsel, for obstruction of an official proceeding, carries an especially stiff sentence — 20 years. The Supreme Court last term, in a case called Fischer v. United States, narrowed the statute’s applicability. A divided court determined that the law’s origin in the Sarbanes-Oxley Act, intended to combat financial fraud, meant that it could not be broadly applied to the events of January 6. Mr. Smith contends that in Trump’s case, the fit between statute and action is a constitutionally snug one.  

Judge Chutkan is expected to rule in Mr. Smith’s favor, but as with almost all Trump’s legal proceedings since he became president, criminal or civil, the matter will almost certainly be decided on appeal, where higher level judges — including Supreme Court justices —  have so far shown themselves to be more open minded about Trump’s arguments.

Any decision Judge Chutkan makes with respect to immunity will be ripe for review by the United States Circuit Court for the District of Columbia Circuit and possibly the Supreme Court. If Trump  is eventually convicted and sentenced to prison, though, he could be immediately remanded into custody, even while he mounts appeals. In the state criminal system, though, defendants are usually allowed to remain at liberty until the final appellate court has ruled. 

Trump also faces state charges in Georgia, in the form of a sprawling racketeering case brought by the district attorney of Fulton County, Fani Willis. About midway between Election and Inauguration Days, on December 8, the Georgia Court of Appeals will hear Trump’s request that Ms. Willis be removed from the case for her secret affair with her one time special prosecutor, Nathan Wade. The two deny their romance preceded the charges.  

Even if Ms. Willis is not removed, the case, which initially charged 19 defendants, could take months or years to unfold. Trump’s attorneys have asked for a delay until 2029 — past the horizon of another presidential term. The former president could also seek to avoid Fulton County Jail by arguing that the Supreme Court’s grant of immunity blocks Ms. Willis’s prosecution.