Chip Somodevilla/Pool via REUTERS

The New York Times reports that on Wednesday, the Supreme Court will "consider for the first time whether to say 'no'" to President Donald Trump "in a lasting way" as they weigh in on the president's "use of emergency powers to impose sweeping tariffs on nearly every U.S. trading partner."

According to the Times, the case is a difficult one, made even worse by Trump's "efforts to personalize the dispute."

"Observers of the court said the justices would be keenly aware that Mr. Trump would perceive a legal defeat as a personal blow," the Times notes.

Donald B. Verrilli Jr., who was the solicitor general during the Obama administration, agrees, saying “You can’t help but think that that’s going to be hovering over the decision-making process in this case."

Thus far, the Supreme Court's six conservative justices have "so far been receptive to Mr. Trump's claims of presidential authority," the Times says.

The tariffs case, however, is the first time the justices will weigh in on "the underlying legal merits" of Trump's actions.

"At the end of this term, we’ll see wins and losses for Trump on presidential power,” said Jack Goldsmith, a Harvard Law School professor and former top Justice Department lawyer under George W. Bush. “This is the case I think is the closest, so I don’t know which way it will cut.”

This case, the Times says, "has divided the conservative legal community."

Trump's lawyers say an obscure 1977 statute "gives him broad authority to impose tariffs when he believes an emergency exists," but that law doesn't mention "tarrifs", "taxes", or "duties," the Times explains.

“Emergency powers are meant to be used in emergencies,” said Michael W. McConnell, a former federal appeals court judge nominated by President George W. Bush, who is leading the coalition of small businesses. “No Supreme Court would want to provoke a confrontation with a president of the United States unnecessarily, but on the other hand, the law is the law.”

University of Texas at Austin law professor Tara Lee Grove says may find it "a stretch" to characterize trade deficits as an emergency, but the '77 statute, she says, is "broad and appears to give the president a lot of discretion."

“The justices will be struggling with whether they want to second-guess any presidential decision about an emergency,” she said.

Court observers have pointed to a dissenting opinion from Judge Richard G. Taranto, who was appointed by President Barack Obama, as a possible guidepost for the Supreme Court’s conservatives, should they back Trump, the Times explains.

Taranto, the Times says, "argued that Congress intentionally used broad language to give presidents flexibility," embodying “an eyes-open congressional grant of broad emergency authority in this foreign affairs realm.”

D. John Sauer, the solicitor general, said Trump's use of the '77 statute to impose tariffs was not an unlimited delegation of power and referred to Judge Taranto’s dissent 10 times in his filing.

Grove says the court will face a “legitimacy dilemma” as "they weigh the implications of their decision for the president’s legacy and the economy."

“No matter what they do in this case, it will be painted as political,” Grove says.

Goldsmith says that he thinks the Supreme Court still has some integrity, but if Trump attends oral arguments as he said he intends to, things can get "awkward."

“I doubt the court wants to be perceived as bowing down to him,” Goldsmith says, but if Trump does show up, “it’s just going to make it harder for them to rule for him.”