WASHINGTON, D.C. — Lawyers for President Donald Trump may have overplayed their hand by arguing that neither he nor his businesses can be investigated by a state prosecutor.

On Monday a federal judge savaged the argument, saying it was “repugnant” to the U.S. Constitution. Now a federal appeals court will weigh in on a legal question never previously considered, and experts said Trump’s expansive claim of broad presidential immunity probably will be rejected if he continues to assert that the president, his businesses and his associates are immune to even an investigation.

“I don’t think there’s a chance in the world that the theory the president is putting forth will be accepted,” said Stephen Saltzburg, a former official in President Ronald Reagan’s Justice Department who now teaches at the George Washington University law school in Washington.

“It really might mean that everyone the president has ever dealt with cannot be investigated if he objects, regardless of how guilty they may be, regardless of what conduct you’re investigating,” he added. “That can’t be right.”

The ruling Monday by U.S. District Judge Victor Marrero in Manhattan is yet another crack in the legal wall Trump has constructed around his personal financial records. Two judges have already ruled against Trump in federal cases over whether Congress can get his financial records, and the president is appealing those decisions. The stakes of the legal fight have only increased with the Democrats starting a formal impeachment inquiry.

In the latest case, Manhattan District Attorney Cyrus Vance Jr. is seeking from Trump’s accountants, Mazars USA LLP, eight years of tax records and other financial documents that may shed light on whether the Trump Organization falsified business records related to hush payments to women claim they had sexual relationships with Trump. The president sued to block the subpoena, advancing a broad reading of immunity that Marrero described as “virtually limitless.”

The case will be heard by a federal appeals court in New York as soon as Oct. 21 and could be taken up by the U.S. Supreme Court. In the meantime, Marrero’s ruling is on hold as lawyers on both sides prepare legal briefs. Along with presidential immunity, the appeals court will consider whether Trump should be required to sue in state court instead of federal court.

In their argument, Trump’s lawyers relied portions of the U.S. Constitution plus a pair of Justice Department opinions: one dating back to 1973, the other issued in 2000 by then-Justice Department lawyer Randolph Moss, now a Washington federal court judge appointed by President Barack Obama. “We believe that the Constitution requires recognition of a presidential immunity from indictment and criminal prosecution while the president is in office,” Moss concluded in 2000.

While binding on Justice Department, the opinions don’t have the force of law, nor should they, at least in the way that Trump’s lawyers desire, Marrero said in his ruling.

“The court is not persuaded that it should accord the weight and legal force the president ascribes to the DoJ memos, or accept as controlling the far-reaching proposition for which they are cited in the context of the controversy at hand,” Marrero wrote.

The memos, he said, have attained an unwarranted popular acceptance, “as if their conclusion were inscribed on Constitutional tablets so etched by the Supreme Court.”

In fact, the Constitution doesn’t explicitly say whether a president can be prosecuted or even investigated criminally. The Justice Department opinions are a product of government lawyers providing their best interpretation of what protections the law provides, based on constitutional separation of powers and the unique constitutional role of the president. But they haven’t been tested by a court, and a state prosecutor like Vance may disagree with the analysis in the memos and try to charge Trump.

Even Marrero recognized that a less sweeping immunity may be available to a president, calling for a “case-by-case approach in which a determination” of whether protection is warranted “is made by the courts.” The judge cited a number of factors that might control, including whether the president or others are under investigation, and whether the suspected crime occurred before or after an election.

While Trump’s lawyers may have a reasonable argument that Trump can’t face state charges while he’s president, they face an uphill battle arguing that neither he or his businesses and associates can be investigated, said Washington lawyer Adam Lurie, who worked in the Justice Department under President Barack Obama.

“It’s possible if not likely the Supreme Court will ultimately have to decide this,” Lurie said.