A federal judge questions whether the president can legally sue agencies he controls
A federal judge has raised serious doubts about whether President Donald Trump’s $10 billion lawsuit against the IRS can move forward, ordering both sides to explain why the case should not be thrown out on constitutional grounds.
U.S. District Judge Kathleen M. Williams, a Miami-based Obama appointee, issued a four-page order Friday questioning the very foundation of the lawsuit. At the center of her concern is a straightforward but legally thorny problem: Trump is suing federal agencies that he, as president, already controls.
A lawsuit unlike any other
Trump, along with his sons Donald Trump Jr. and Eric Trump and a company that manages much of the family’s business holdings, filed suit in January against the IRS and the Treasury Department. The lawsuit stems from the unauthorized leak of Trump’s confidential tax returns during his first term.
Charles Littlejohn, a former IRS contractor who worked through Booz Allen Hamilton, pleaded guilty in 2023 to stealing and disclosing the tax information of Trump and other wealthy Americans to publications including The New York Times and ProPublica. He was sentenced to five years in prison in 2024.
Trump’s legal team argues that the IRS and Treasury failed to maintain adequate security protocols despite prior warnings about longstanding vulnerabilities. They are seeking $10 billion in damages.
The constitutional problem at the center of the case
Williams is not disputing that the leak was serious. What she is questioning is whether the lawsuit represents a genuine legal dispute at all.
For a federal court to hear a case, the Constitution requires that two truly opposing parties face each other in what lawyers call an adversarial proceeding. Williams wrote that it is unclear whether Trump and the defendant agencies are sufficiently opposed to each other to satisfy that requirement.
The problem is compounded by Trump’s own executive orders. He has signed directives tightening presidential control over executive branch agencies, including one that bars government employees from advancing legal positions that contradict the president’s view on matters of law. That order puts the attorney general, who is legally required to defend the IRS in court, in a difficult position: defend the agency, or follow the president’s mandate.
Williams put it plainly in her order, noting that the arrangement raises serious questions about whether the parties are truly in conflict with one another.
Trump himself appeared to acknowledge the awkwardness of his position shortly after filing the suit. During a trip on Air Force One in January, he told reporters the situation was unusual and floated the idea of donating any winnings to charity.
Settlement talks already underway
Adding another layer of complexity, Trump’s lawyers recently requested a 90-day extension to pursue settlement discussions with the Justice Department. If those talks produce a monetary agreement, the payout would come from the same federal government Trump now leads, meaning his own administration would effectively be paying his family.
Williams denied the extension request but ordered both sides to submit briefs on the constitutional questions by May 20. A hearing is set for May 27.
A group of former government officials filed an amicus brief last month expressing concern about the broader implications of the case. They argued that Trump’s control over both sides of the litigation creates the conditions for what they described as collusive legal tactics, and that treating the case as routine would threaten the integrity of the justice system.
CNN Senior Legal Analyst Elie Honig described Williams as identifying the core irregularity of having essentially the same person in interest on both sides of a lawsuit. The underlying privacy violation, he noted, would be a valid claim under ordinary circumstances. The conflict of interest, however, is what makes this situation legally extraordinary.
Trump’s legal team responded to Williams’ order by condemning the original leak but did not directly address her constitutional concerns. The Justice Department had not responded to requests for comment as of Friday.