The selection of Judge Alvin Hellerstein to preside over the trial of President Nicolás Maduro of Venezuela could be seen as inauspicious for the Trump administration, though the 47th president is applauding the choice — for now.

Judge Hellerstein, a district judge of the Southern District of New York, was randomly selected to preside over the case after Mr. Maduro and his wife Ceilia Flores, who also faces criminal charges, were seized in Caracas by American forces as part of a daring raid to bring the Maduros to justice. The senior judge, who is 92 years old, was appointed to the bench by President Bill Clinton.

President Trump, aboard Air Force One over the weekend, declared, perhaps without having been briefed on the judge’s previous rulings, that Judge Hellerstein is “very respected, a highly respected judge. We’ll see how we do. The case is, it’s infallible.” The president acknowledged that “We’re just going to go through a slog of a trial.” The prospect of such a “slog” prompted the legal analyst Jeffrey Toobin to write in the Times that Judge Hellerstein “must step aside” on account of his age.

During Judge Hellerstein’s three decades on the federal bench he has not hesitated to rule against Mr. Trump. In 2020, he ordered the release of Mr. Trump’s erstwhile lawyer, Michael Cohen, from prison to home confinement. Mr. Cohen previously pleaded guilty to nine felonies and served some three years in prison. Judge Hellerstein ruled that the refusal to release Mr. Cohen was driven by retribution from the White House. 

Judge Hellerstein has also repeatedly rejected Mr. Trump’s efforts to move his Stormy Daniels hush money case — which centers on payments to the adult film performer facilitated by Mr. Cohen — to a less hostile federal court. The judge ruled that “Reimbursing Cohen for advancing hush money to Stephanie Clifford cannot be considered the performance of a constitutional duty.” That ruling led to Mr. Trump’s 34 convictions in a Manhattan courtroom.

A panel of the Second United States Appeals Circuit, which oversees Judge Hellerstein, ordered him to reconsider that ruling in the wake of the Supreme Court’s immunity decision in Trump v. United States. The panel reasoned that Judge Hellerstein “did not consider whether certain evidence admitted during the state court trial relates to immunized official acts or, if so, whether evidentiary immunity transformed the state’s case into one that relates to acts under color of the presidency.”

The Second Circuit decided to “leave it to the able and experienced District Judge to decide whether to solicit further briefing from the parties or hold a hearing to help resolve these issues. We express no view and ‘neither rule nor imply’ that the District Court should resolve Trump’s motion …  in any particular way.” Mr. Trump is also appealing the case, which he calls the “most politically charged prosecution in our nation’s history,” in the New York state system.

Judge Hellerstein will be doing double duty weighing the cases against Messrs. Maduro and Trump simultaneously. The Manhattan district attorney, Alvin Bragg, owes the judge his brief arguing for why the prosecution ought to remain in state court on Wednesday. Mr. Trump’s response is due on January 21, and oral arguments on the issue of federal removal are scheduled for February 4. The next conference in the Maduro matter is March 17.

Last year Judge Hellerstein presided over a challenge mounted by two Venezuelans to their removal under the Alien Enemies Act. He found the government’s use of that statute unconstitutional, and ordered that they be afforded at least the rudiments of due process. Judge Hellerstein called the prison in El Salvador where the detainees were due to be sent “a notoriously evil jail.”

Judge Hellerstein also was assigned the first indictment of Mr. Maduro, in 2020.