Former President Trump’s battle against the Justice Department investigation into the mishandling of government records at Mar-a-Lago has now reached the highest court, but legal experts say he may not fare as well as his case is pushed before new judges. 

Trump scored an initial victory before a federal district court judge in Florida, who granted his request to appoint a special master to review the more than 10,000 government documents seized at his home to determine whether any might be protected by the executive or attorney-client privileges. 

But as the case works its way through the court system, other judges seem more hesitant to grant Trump’s requests. 

The 11th Circuit Court of Appeals served the Department of Justice (DOJ) an initial victory in the case, siphoning off the more than 100 classified records from special master review and later agreeing to an expedited schedule to review DOJ’s challenge to Judge Aileen Cannon’s decision to approve the special master process. 

But Trump’s emergency appeal to the Supreme Court wasn’t treated like an urgent matter — Justice Clarence Thomas gave DOJ a week to respond.  

“All indications are that the appellate litigation continues to move in the government’s direction,” Brad Moss, a national security law expert, told The Hill. 

“The 11th Circuit is expediting the appeal of the special master appointment, and the Supreme Court is conversely taking its sweet time considering Mr. Trump’s appeal of the lifting of Judge Cannon’s injunction. If nothing else, the appellate judges are making clear how serious they take the government’s national security concerns and how little credence they place in Mr. Trump’s legal theories.” 

Trump’s appeal to the Supreme Court to intervene in the case was the latest step from a legal team that’s taken an aggressive posture in its battle with the Justice Department. 

But the filing itself was actually quite narrow. 

The request from Trump asks that the classified records in question are returned to the pool of documents included under the special master review, opting not to ask the court to exclude those documents from being used by the Justice Department as they continue their investigation — something Cannon had included in her original order. 

“This is a very specific and narrow request by Trump, the merits of which turn on a technical jurisdictional question, but which runs into fatal procedural obstacles long before that. It’s not laughable, but only because it’s small,” Steve Vladeck, a professor at the University of Texas School of Law specializing in federal courts and national security law, wrote on Twitter.  

“This is what good lawyers who are stuck do to appease bad clients….It’s a way of filing *something* in the Supreme Court without going all the way to crazytown and/or acting unethically,” Vladeck added. 

Trump’s lawyers argued that the federal appeals court erred by allowing the Department of Justice to appeal a move that was procedural in nature. 

They argued the appeal “impairs substantially the ongoing, time-sensitive work of the special master” and said the 11th Circuit’s intervention “effectively compromis[es] the integrity of the well-established policy against piecemeal appellate review.” 

Trump’s team also recycled legal arguments from earlier briefs insinuating that he could have declassified the records in his home but stopped short of doing so. It’s a statement that generated skepticism from the special master, who initially asked the legal team to back the claim before Cannon stepped in and said Trump did not need to comply with the request. 

Even if Trump convinced the court, the DOJ would still be able to use the documents in its investigation even as the special master reviewed them. 

Moss, likewise, suspected the filing is likely to accomplish little for Trump. 

“The appeal to the Supreme Court by the Trump legal team was done for one reason: Mr. Trump no doubt demanded something be filed. The narrowness of the appeal reflects the efforts by his lawyers to craft something — anything — they could justify as non-frivolous. Even if it succeeds, it would likely come too late in the special master process anyway to matter,” he said. 

Brian Greer, a former attorney for the CIA, sees one potential upside for Trump — but only if the Department of Justice decides to prosecute him. 

“Even if Trump is granted the relief they’re seeking, it’s not clear how helpful it’s going to be to them other than getting early access to those classified records,” he told The Hill.  

“To me, the only real end game with the Supreme Court litigation, other than delay, is getting access to those records prior to an indictment so that they can start building their defense.” 

The 11th Circuit agreement to an expedited review for the Justice Department’s case could also prove helpful for the government. 

In its initial ruling, a three-judge panel for the court suggested Cannon erred by appointing the special master, a sign it may be convinced Trump has little claim as a former executive to any of the documents. 

But as a practical matter it also aids their investigation. 

“The Justice Department is correct in asserting that being unable to use the unclassified documents currently before the special master could hinder its ongoing investigation into the classified records,” Greer said. 

“That’s because, as the Justice Department asserted, they may want to explore how those unclassified documents were commingled with the classified records, whether there are fingerprints on those documents, and to ask witnesses about those documents, all of which might be relevant to investigating the classified records,” he continued. 

But the victories for the Department of Justice still delay the ultimate determination on the records. 

The process before the 11th Circuit and Supreme Court could take months, and a ruling from the appeals court would likely come in December at the earliest. 

“The timing is still not great for DOJ as they would likely want to complete any investigation involving the relevance of the unclassified records prior to bringing charges on the classified records,” Greer said.