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The court will spend hours in teleconferenced hearings - with the world listening in - on three cases with potential landmark constitutional consequences. All concern Trump's long-running legal fight to shield years of income tax returns from public view and keep his private financial records from the hands of Democratic-led House committees and a New York district attorney.
The court's conclusion this summer will carry major implications for the limits of presidential power and accountability, and could affect the fall election.
Also at stake is the public's perception of the court itself. Chief Justice John Roberts already this year has presided over Trump's impeachment trial and no doubt hopes the court can emerge from this legal showdown, regardless of outcome, with its reputation of neutrality intact.
After losses in each court that has considered his request, the president is aggressively arguing that subpoenas to banks and an accounting firm for years of financial records from him, his company and his family are unprecedented attacks on the presidency itself.
But previous presidents - Republican Richard Nixon and Democrat Bill Clinton - have made similar arguments about the deference owed the occupant of the White House and come away empty-handed. Both resulted in rulings against the chief executives, and the presidents' own nominees joined in the unanimity.
In one of the current cases, involving Manhattan District Attorney Cyrus Vance's investigation of Trump under New York state laws, Trump's lawyers repeatedly remind the court of the past views of Justice Brett Kavanaugh.
They quote a 2009 law review article written by Trump's most recent addition to the Supreme Court: "A President who is concerned about an ongoing criminal investigation is almost inevitably going to do a worse job as President."
But there's a striking difference in this showdown at the Supreme Court than with previous cases that tested Trump's power as president.
His major backer is his own Justice Department, which says the subpoenas are improper but does not fully embrace the legal arguments of the president's private lawyers. The number of amicus briefs filed on Trump's behalf are dwarfed by those on the other side.
Especially striking is the absence of supportive briefs from red-state attorneys general and Republican members of Congress, who have been stalwart backers of the president as he moved policy in a conservative direction, such as his ban of travelers from certain countries.
Instead, the briefs supporting Congress and Vance come from former members of the Justice Department and Republican executive branch officials.
Donald Ayer, a deputy attorney general under President George H.W. Bush, said that is because Trump has gone too far in building an imperial presidency: spending money Congress has appropriated for other purposes in the case of Trump's signature southern border wall; forbidding current and former administration officials, including former White House counsel Donald McGahn, from testifying before Congress; and now invoking claims that he should be able to stymie congressional and criminal investigations into Trump's private conduct before he became president.
"They waive this claim of absolute immunity like a talisman," Ayer said in an interview.
He joined a brief in the Vance case put together by the Protect Democracy Project. It is filed on behalf of former Republican members of Congress and the executive branch "concerned that President Trump's assertions of absolute immunity from process while in office - and more generally, his arguments against accountability in any forum - could impose lasting damage on our constitutional system of checks and balances as well as on the rule of law."
It is true that Trump's private lawyers have adopted a sweeping view of presidential immunity in all three of the cases the court will hear.
Two of them, Trump v. Mazars and Trump v. Deutsche Bank, concern the attempts of three House committees to bypass the president to obtain his financial records from his longtime accounting firm and financial institutions. The committees say they are needed to check the president's financial disclosures and whether conflict-of-interest laws are tough enough.
In Trump v. Vance, the president is attempting to stop subpoenas from a grand jury Vance is supervising. He is looking into whether corporate records were altered in violation of state laws to cover up hush-money payments.
The cases are similar in that they are seeking much the same information. Included are Trump's tax returns, which every president since Jimmy Carter has made public but Trump has steadfastly guarded.
They also seek much more. The congressional committees "demand information about seven business entities, as well as the personal accounts of President Trump, Donald Trump Jr., Eric Trump, and Ivanka Trump," said the brief filed by the president's private lawyers Jay Sekulow and William Consovoy.
"The Committees also demand the banking records for all of the named individuals' immediate families - i.e., spouses, minor children, and, in the President's case, grandchildren."
The congressional subpoenas followed testimony from Trump's former fixer and attorney Michael Cohen, who told lawmakers that Trump had exaggerated his wealth to seek loans. Two committees subpoenaed Capital One and Deutsche Bank as part of their investigation into Russian money laundering and potential foreign influence involving Trump.
Federal judges in New York and the District of Columbia - at the district court and appeals court levels - moved swiftly by court standards and repeatedly ruled against Trump and to uphold Congress' broad investigative powers.
In Washington, a divided panel of the U.S. Court of Appeals for the D.C. Circuit in October rejected Trump's assertion that Congress' subpoena was an unconstitutional attempt to harass the president that lacked a "legitimate legislative purpose."
The appeals court upheld a ruling from U.S. District Judge Amit Mehta, who wrote, "It is simply not fathomable that a Constitution that grants Congress the power to remove a President for reasons including criminal behavior would deny Congress the power to investigate him for unlawful conduct - past or present - even without formally opening an impeachment inquiry."
A panel of the U.S. Court of Appeals for the 2nd Circuit in New York agreed.
Trump's lawyers told the Supreme Court ahead of Tuesday's arguments that the House subpoenas for the personal records of a sitting president are unprecedented, go beyond Congress' authority into the realm of law enforcement and are intended to harass Trump for political purposes.
"These Committees are not legislating; they are avowedly engaging in law enforcement. All of them - to one degree or another - have acknowledged that the purpose of the investigations is to determine whether the President engaged in wrongdoing," the lawyers wrote, calling the demand "a recipe for constitutional crisis."
The Justice Department, which joined in defending the president in his official capacity, echoed Trump's lawyers in arguing that congressional subpoenas must serve a legitimate legislative purpose, cannot be issued simply to expose wrongdoing and must be authorized by a delegation from the full chamber.
The department said Congress has not met the heightened standards required when it comes to matters involving the chief executive.
"Those limitations should be even stricter when a committee aims its investigatory power at the president," said the Justice Department brief.
But the House said that it is the president who is trying to invoke a crisis and that congressional powers are well-settled.
"Many momentous separation-of-powers disputes have come before this court," wrote Douglas Letter, general counsel for the House. But this dispute, he said, "is not one of them."
"Contrary to what President Trump and the solicitor general contend, there is nothing unprecedented about congressional subpoenas for documents that may shed light on presidential affairs."
A brief from general counsels who worked for House speakers - including Republicans Dennis Hastert, Newt Gingrich, Paul Ryan and Democrat Nancy Pelosi - counted the ways in which sitting presidents are not beyond the reach of subpoenas.
In the 1800s, Chief Justice John Marshall issued a subpoena ordering President Thomas Jefferson to produce private communications Aaron Burr viewed as critical in defending against charges of treason.
In the 1990s, a special Senate committee investigating the real estate deals of Bill and Hillary Clinton issued subpoenas for access to presidential records, including White House phone records from the telephone company and Hillary Clinton's attorney billing records from when she was in private practice.
Stephen Vladeck, a constitutional law professor at the University of Texas who is not involved in the cases, said the "sum total of the president's argument in these cases is that it is just about impossible for Congress to conduct oversight of alleged personal improprieties by the president and that the only possible mechanism is through a formal impeachment investigation."
The problem with that argument, Vladeck said, is how can Congress know whether an impeachment investigation is justified without any opportunity to gather information from the executive branch?
In Trump v. Vance, the president's lawyers have made an even more sweeping claim: that the president has "temporary presidential immunity" not only from prosecution but also from investigation.
In response to a hypothetical question from a judge on the 2nd Circuit last fall, Consovoy said the immunity would apply even if the president were to shoot someone in the middle of a busy street.
Vance is seeking records from the Mazars USA accounting firm as part of his investigation into whether Trump business records were falsified to cover up hush-money payments that Cohen testified he made just before the 2016 election to two women - pornographic film actress Stormy Daniels and former Playboy model Karen McDougal - who alleged they had affairs with Trump. Trump has denied their claims.
The appeals court unanimously rejected Trump's claim that a state investigation would interfere with the president's ability to conduct the nation's business.
"The subpoena at issue is directed not at the president, but to his accountants; compliance does not require the president to do anything at all," Chief Judge Robert Katzmann wrote for the court.
The president's lawyers make similar arguments at the Supreme Court.
"The risk that politics will lead state and local prosecutors to relentlessly harass the President is simply too great to tolerate," they wrote. "The President must be allowed to execute his official functions without fear that a state or locality will use criminal process to register their dissatisfaction with his performance."
Vance replied that there is no precedent for what the president seeks.
"The States are central to the Nation's criminal justice system, and state prosecutions are cloaked with a presumption of regularity that makes federal interference particularly inappropriate," his brief states. "Existing structural constraints - including jurisdictional limitations, ethical rules, and the prohibition on state investigation of official presidential conduct - further mitigate any risk of harassing or overly burdensome state investigations."
The Supreme Court asked all parties to address whether the disputes were a "political question" beyond reach of the judiciary. All said last week that the court should reach the merits of the cases.
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