This is the Trump Docket, where we track some of the most important legal cases of the Trump presidency and how their results could shape presidential power. Questions, comments, or thoughts about cases to cover? Email us here.

Two years into Donald Trump’s presidency, we still know relatively little about the inner workings of his family business, the Trump Organization. But on Tuesday, a case that could force the company to reveal some information about its finances faces a big test in a federal appeals court in Virginia. Judges will hear oral arguments over whether a lawsuit alleging that President Trump is violating the Constitution by accepting payments from state officials and foreign diplomats at his Washington, D.C., hotel, which the Trump Organization operates, can go forward. The case is one of a trio of lawsuits that were filed relatively early in Trump’s term and claim that the president is violating two little-known clauses of the Constitution that prohibit federal officials from accepting titles, gifts or “emoluments” from foreign countries, the federal government or state governments.

Legal experts initially predicted that the cases wouldn’t make it very far. But last year, a federal judge in Maryland handed down a series of rulings in favor of one set of challengers — Washington, D.C., and Maryland — allowing them to issue subpoenas for financial information related to the hotel from several branches of the Trump Organization. In response, Trump appealed to the 4th U.S. Circuit Court of Appeals in Virginia to get the case thrown out — or, barring that, to at least temporarily stop it from moving forward. And the outcome of this high-stakes case could hinge on how the court chooses to interpret “emolument” — a word that dropped out of our common lingo more than a century ago.

It’s rare for judges to be faced with a legal issue that is actually novel, particularly when it comes to the Constitution. But the emoluments clauses, which were initially designed to guard against influence from foreign and other governments, are truly arcane. “The Supreme Court has never ruled on the constitutional meaning of the word ‘emolument,’” said Georgetown law professor John Mikhail, who co-authored an amicus brief in support of D.C. and Maryland on the history of the word.

In other words, what the founders meant when they barred federal officials and the president from accepting emoluments is a central question in this case, although the appeals court judges will also have to consider other issues, like whether the states have the authority to bring the suit in the first place. Trump’s attorneys have contended that the president is not in violation of the emoluments clauses because they specifically refer to a payment for a service — like a salary or consulting fee — accepted from a foreign or state government in one’s official capacity as president. Trump’s opponents, on the other hand, have argued for a much broader definition that includes any kind of benefit or profit gained from a foreign or state government during one’s presidency, which would encompass payments received from foreign countries or state officials at Trump’s hotel.

Whether this argument will hold water in the courts is hard to know, because there isn’t a very decisive paper trail on the emoluments clause. Over the years, executive branch lawyers have issued guidance about particular situations that involve potential emoluments clause violations — for example, former President Barack Obama checked in with the Justice Department after he won the Nobel Prize, to make sure that accepting the cash award wouldn’t run afoul of the Constitution. (The department said it didn’t.) But Trump’s sprawling business empire and his decision not to fully divest himself from his companies make this a unique case.

As a result, Trump’s lawyers, his opponents and independent researchers have headed for 18th-century dictionaries and historical linguistic databases to try to figure out what “emoluments” meant at the time the Constitution was drafted. After the emolument lawsuits were filed, Mikhail examined dozens of dictionaries published over a several hundred-year period before around 1800 and concluded that broad definitions were overwhelmingly common. And a study completed earlier this year drew on “corpus linguistics,” a method that uses large sets of data to analyze language — in this case, databases of historical documents drawn from the founding era. The authors submitted a brief to the Virginia court outlining their findings. Clark Cunningham, one of the study’s authors and a law professor at Georgia State University, told me that the president’s argument that “emolument” had a specific, narrow meaning “is just not consistent with the data.” In the thousands of uses of “emolument” examined in the study, Cunningham and his co-author found that the word often referred to personal and private transactions. And Cunningham said that its proximity to other nouns like “bounties,” “fees” or “privileges” indicates that it was used as a catch-all term, which suggests that the definition was broader than the one offered by Trump’s lawyers.

But other legal scholars have pointed to historical examples that challenge a broad interpretation of the emoluments clauses. In a brief supporting Trump’s position, one of those scholars argues that George Washington bought federal land at auction while he was president, which could constitute a violation of the domestic emoluments clause under a broader definition. “The whole world saw that — why didn’t anyone complain?” said Seth Barrett Tillman, who is a lecturer in law at Maynooth University in Ireland and studies the foreign emoluments clause. He believes that even though the term may have regularly been used in the broader sense at the time the Constitution was written, examples like this support the idea that the founders intended for a more restrained version of “emolument” to apply.

The lower court judge in tomorrow’s case drew extensively on Mikhail’s study to support his conclusion that a broad definition of “emolument” was warranted. But other judges may not agree. And whatever the appeals court rules, it likely won’t be the last word. If the president loses, legal experts told me that he’ll almost certainly appeal to the Supreme Court. Ironically, the use of corpus linguistics is most popular among conservative judicial originalists like Supreme Court Justice Clarence Thomas, who emphasize the need to interpret legal provisions based on the way they were understood when they were written. But getting a five-justice majority on the Supreme Court to agree that the states have the ability to bring an emoluments lawsuit against the president could be a tough sell, according to Andy Grewal, a law professor and emoluments expert at the University of Iowa, because generally, presidents are considered to have broad protections from civil lawsuits.

What’s perhaps most striking, at this point, is the way the emoluments cases have slowly evolved from a minor nuisance to a real threat to the president. If the appeals court allows the emoluments trial to go forward, Trump will be forced to divulge financial information about his hotel that he has fought for years to keep private. It’s a testament to both the ways that Trump’s presidency is testing our legal and constitutional system and the extent to which Trump’s opponents have used that same system to attack him.

Other cases

Pre-presidency Trump

A state appeals court in New York ruled that a sitting president can be sued in state court, rejecting Trump’s challenge to a defamation lawsuit filed against him in New York by a former contestant on “The Apprentice.” Their ruling is unlikely to be the final word, however — Trump’s attorneys have said they will appeal to the New York Court of Appeals, which is the state’s highest court, and if they fail there, the case will likely end up at the U.S. Supreme Court.

Paul Manafort, Trump’s former campaign chairman, was sentenced to 47 months in prison and ordered to pay $25 million in restitution by a federal judge in Virginia and was sentenced to an additional 43 months in Washington, D.C., bringing his total prison time to 7.5 years. The sentencing closes one of the most high-profile threads of special counsel Robert Mueller’s investigation into Russian interference with the 2016 election. However, Manafort was indicted on a new set of charges in state court in New York shortly after his sentencing in D.C.

In another thread of Mueller’s probe, a trial date was set for Nov. 5 in the case involving Roger Stone, a longtime Trump adviser who was charged in January with lying about his attempts to contact WikiLeaks during the 2016 election.

Former national security adviser Michael Flynn asked for a delay in sentencing, saying he’s still cooperating with federal investigators in connection with the Russia probe. Sentencing for former Trump campaign aide Rick Gates was also postponed while he continues to cooperate with Mueller’s team.

A federal judge closed Stormy Daniels’s lawsuit against President Trump, which had sought to void a “hush” agreement she signed during the 2016 campaign that gave her $130,000 in exchange for her silence about a past affair she says she had with Trump. The decision was expected, as Trump and his attorneys had said they wouldn’t enforce the nondisclosure agreement, which Daniels violated repeatedly.

President Trump

Later this month, a panel of judges on the 2nd U.S. Circuit Court of Appeals will hear oral arguments in a case about whether Trump can block critics on Twitter without violating the First Amendment. A lower-court judge ruled last year that this is unconstitutional.

The Trump administration

The Trump administration’s restrictions on military service by transgender people will be implemented next month, after a federal judge in Maryland lifted the last remaining injunction against it. However, legal challenges to the policy will continue to unfold in the courts, even after it goes into effect.

A second federal judge ruled that the Trump administration’s attempt to add a citizenship question to the 2020 Census is unconstitutional. The Supreme Court will hear oral arguments on the legality and constitutionality of the citizenship question in April.

Following a court order last year, the Trump administration agreed to extend temporary protected status for immigrants from El Salvador, Haiti, Sudan and Nicaragua, which the Department of Homeland Security had initially tried to end. However, the administration left open the possibility that protections could be rescinded later if it ultimately prevails in one of the ongoing court challenges involving the policy.

Another judge ruled that the Trump administration’s attempts to withhold law-enforcement funding from cities and states with “sanctuary” policies are illegal. Despite ongoing lawsuits on the issue, almost all the cities and states that were initially denied law-enforcement grants have received their 2017 funds, according to The Associated Press — despite the fact that some haven’t changed their sanctuary policies to comply with the government’s grant conditions.

CORRECTION (March 18, 2019, 12:05 p.m.): A previous version of the first bullet point in the “Other cases” section incorrectly identified New York’s highest court. It is the New York Court of Appeals, not the New York Supreme Court.

Trump’s lawyers head to court