In what can only be described as a judicial plot twist worthy of a prestige television finale, Special Counsel Jack Smith’s prosecution of former President Donald Trump over allegedly hoarding classified documents at Mar-a-Lago has encountered a fresh legal wrinkle, courtesy of the presiding judge who never misses an opportunity to keep everyone on their toes or perhaps just scratching their heads.
U.S. District Judge Aileen Cannon, who was appointed to the bench by Trump in 2020, issued a curious ruling that has left legal analysts both perplexed and reaching for their constitutional law textbooks. Specifically, she requested both the defense and prosecution prepare proposed jury instructions addressing the mind-bending possibility that Trump was legally entitled to possess the documents under the Presidential Records Act. Smith’s team, clearly not amused by this novel legal theory, fired back in a court filing Tuesday, calling the proposed rationale “fundamentally flawed” and asserting that it would result in the “distortion” of a very straightforward proceeding about whether boxes of state secrets should have been left sitting next to the pool towels in Palm Beach.
To add a little more zest to the drama, Trump, as is custom these days, has pleaded not guilty to all 40 felony charges against him, which include willful retention of national defense information and obstruction of justice, charges that typically do not end in a decorative slap on the wrist. The case, bubbling along in Florida, had been on the slow burner of judicial timelines, with delays piling up like unread emails. But this ruling raises the unsettling possibility that the courtroom may soon double as a forum for legally creative fan fiction about what presidents can and cannot do with top secret documents once they leave office.
Smith’s team argued that the notion a former president could declare classified materials as personal property just by quietly thinking it so is neither law nor logic, but perhaps something that belongs in a wishful diary entry. Prosecutors noted it could lead a jury to believe Trump’s actions were entirely lawful, which they say flies in the face of decades of historical record, legislative intent, and basic common sense. Meanwhile, one suspects at least a few government lawyers are having trouble sleeping at night knowing their prosecution hangs in part on interpretations of statute that now feel like law-school hypotheticals gone rogue.
“In general,” wrote the prosecution, with barely concealed exasperation, “a jury should not be instructed on a factual theory of the defense that is legally invalid.”
And while Cannon has not ruled definitively on whether this legal curveball will make its way into the final jury instructions whenever the trial finally takes place, her invitation to both sides to provide competing scenarios has poured fresh uncertainty into an already surreal case that was never going to resemble an orderly pen-and-plead procedural.
The trial remains unscheduled, delays persist, and even Lady Justice appears to be glancing toward the exits in search of a stiff drink.
Because when it comes to this courtroom drama, reality keeps auditioning for the role of satire.

