CNN  — 

If at first you don’t succeed, try, try again.

The right wing Supreme Court majority built by ex-President Donald Trump has ruled just as conservatives had hoped on politically charged cases on abortion, climate and religion. Yet it has been far less tolerant of his efforts to block congressional investigators’ access to presidential records as well as prosecutors’ access to tax records and of his spurious election fraud claims. So Trump’s latest appeal to the nine justices in the Mar-a-Lago documents furor – another apparent delaying tactic – may be a long shot and could even backfire.

Trump on Tuesday filed an emergency application to the court to step into his dispute with the Justice Department over documents marked classified that he hoarded at the resort in Florida.

Unlike his frequently more florid and fantastical legal gambits, this one is narrow and legally nuanced – far smaller than a possible broader attempt to test an ex-president’s scope to claim executive privilege or some kind of claim that the search on his home in August was illegal. Instead, Trump wants the court to ensure that more than 100 documents designated as classified are included in a review by a third party official known as a “special master.”

The ex-President has every legal right to take such a step. But it’s also the case that Trump’s team has repeatedly sought to slow down the Justice Department’s classified documents probe in the courts, which reflects his characteristic desire to postpone accountability. In this case, any delays could push it closer to a possible Trump 2024 presidential campaign and fuel his claims of political persecution.

But, just as in other recent filings by Trump to the Supreme Court, the tactic may not work, according to legal experts.

  • There is no guarantee that the court, already being dragged deep into politics, will perceive this case as bearing such vital constitutional or legal importance that failing to take it up would be a dereliction of duty.
  • Even if it decides to hear the case, the court may move more swiftly than Trump hopes. Justice Clarence Thomas, for instance, on Tuesday quickly gave the Justice Department until 5 p.m. on October 11 to provide a response to Trump’s appeal.
  • And Trump could simply lose – even if he persuades the justices to take the case – since to get emergency relief he must prove that he’s suffered irreparable harm in the matter, a threshold many legal experts believe is a stretch.

“The Supreme Court has not looked very kindly on former President Trump in cases that he’s brought with respect to documents and his personal property both when Congress was the one seeking information from him and other government entities were the ones seeking information from him,” said Elliot Williams, a CNN legal analyst and former Justice Department official.

“He’s pretty consistently lost those cases. And it’s not hard to see how either the court just doesn’t take this up or rules against him if they do.”

The Supreme Court has often frustrated Trump

Trump has built a personal record of frustration before the Supreme Court.

In January, the court declined to block a handover from the National Archives of 700 documents that the House select committee probing the US Capitol insurrection said that it needed for its investigation. The Supreme Court several times rejected challenges to the 2020 election. The court has also ruled that the then-President was not immune from a New York subpoena in a criminal investigation seeking his tax records.

Trump has long appeared to believe that judges he appointed owe him loyalty. He nominated three of the Supreme Court’s nine justices – Neil Gorsuch, Brett Kavanaugh and Amy Coney Barrett.

And he has typically reacted badly to his defeats before the top bench. In December 2020, for instance, he tweeted that the court had let him down and displayed neither wisdom nor courage in dismissing a challenge to the election.

But sometimes even humiliating court defeats can bring Trump other benefits.

While it is too early to predict how the court will handle this case, just bringing it to them works for Trump in a number of political ways.

It keeps him in the news and fuels a sense among his supporters that he is being treated unfairly. As in this case, Trump often substitutes a political or public relations strategy for a strong legal one. And it would be no surprise to see Trump fundraising off of his emergency request.

His latest move is also consistent with his habit of using every possible avenue in the legal system to slow a case or fog it up. Taking that a step further, CNN legal analyst Steve Vladeck suggested that the application to the court partly came across as an attempt by his team to placate a highly litigious client.

“This is what good lawyers who are stuck do to appease bad clients: The jurisdictional argument is narrow, technical, and non-frivolous. It’s a way of filing *something* in the Supreme Court without going all the way to crazytown and/or acting unethically,” Vladeck, a University of Texas law professor, wrote on Twitter.

‘Thin’ arguments about a legal emergency

Specifically, Trump’s emergency request does not ask the Supreme Court to restore a hold that district court Judge Aileen Cannon, whom he nominated, had imposed on the Justice Department accessing those documents marked as classified as it investigates their retention at Mar-a-Lago.

He instead wants the classified documents at issue included in a review by the special master after the 11th Circuit Court of Appeals sided with the DOJ and exempted them from the review process.

The department had argued that including those documents in the special master review would harm national security.

But Trump’s team pushed back, saying in Tuesday’s filing that this position “cannot be reconciled” with the DOJ saying it may want to show those same documents to a grand jury or to witnesses during interviews.

And the application opened with a highly political argument – claiming that the “unprecedented circumstances” of the case represented an “investigation of the Forty-Fifth President of the United States by the administration of his political rival and successor” – that took large liberties with the facts of the Mar-a-Lago case.

That reasoning struck former White House counsel John Dean as “thin.”

“I didn’t see much of an emergency,” Dean, who was at the center of the Watergate scandal that brought down President Richard Nixon, told CNN’s Anderson Cooper on Tuesday.

“The arguments are highly technical and not the sort of thing the Supreme Court, I would think, would want to get into given their current standing in public opinion.”