U.S. District Court Judge Kathleen Williams, an appointee of former President Barack Obama, issued a four-page order questioning whether the case presents a genuine legal dispute, given that Trump holds ultimate authority over the very government lawyers who would defend the IRS.

“Although President Trump avers that he is bringing this lawsuit in his personal capacity, he is the sitting president and his named adversaries are entities whose decisions are subject to his direction,” Williams wrote. She added that it was “unclear to this Court whether the Parties are sufficiently adverse to each other so as to satisfy the Constitution’s case or controversy requirement.” The judge set a May 20 deadline for briefs on the issue, signaling that the novel legal question could derail the suit before it reaches the merits.

Trump has acknowledged the awkwardness of the arrangement. Shortly after filing the suit in January, he told reporters on Air Force One that it was “very interesting” to be on both sides of a lawsuit and mused about donating any proceeds to charity. Last year, speaking about a separate $230 million claim he filed with the Justice Department over the FBI raid on Mar-a-Lago, Trump was even more blunt. “It sort of looks bad, ‘I’m suing myself,’ right?” he said at the time.

The lawsuit stems from the leak of Trump’s tax returns, which were published by The New York Times in 2020. Trump and his co-plaintiffs, including his sons Eric and Donald Jr. and a company that controls much of the family business empire, allege that IRS employees improperly disclosed confidential tax information. The suit seeks $10 billion in damages, an amount that would dwarf typical privacy settlements.

Unitary executive theory complicates the case

Williams pointed to Trump’s own executive orders as a central complication. One order, signed last year, advances a legal theory known as the unitary executive, under which the president wields full control over the actions of most or all executive branch employees. The order essentially forbids government employees acting in their official capacity from advancing legal positions at odds with those staked out by the president.

“One such employee of the executive branch, the Attorney General, has a statutory obligation to defend the IRS when it is hailed into court, but then is ostensibly required by executive mandate to adhere to the President’s opinion on a matter of law in such a case,” Williams wrote. “This raises questions here over whether the Parties here are truly antagonistic to each other.” The judge noted that Trump’s efforts to consolidate power over the executive branch through such orders directly undercut the adversarial posture that federal courts require.

Legal experts said the judge’s skepticism was well-founded. The case presents a rare collision between Trump’s personal legal interests and his constitutional role as head of the executive branch. If Williams rules that the parties are not sufficiently adverse, the lawsuit could be dismissed on jurisdictional grounds, sparing the IRS from having to defend against a $10 billion claim brought by its own commander in chief.