Special Counsel Jack Smith continues to encounter setbacks in his legal endeavors. According to one expert, Smith now may face a significant obstacle in leveraging evidence against former President Donald Trump in the classified documents case in Florida.

This follows the transfer of grand jury investigation files from Washington, D.C., to the court of Judge Aileen Cannon, a Trump appointee. Bill Shipley, a former prosecutor, suggested that the transfer grants Cannon the authority to control the grand jury testimony, potentially benefiting Trump.

“Because the case wasn't going to be prosecuted in D.C., the rulings made as part of the grand jury investigation are not binding on Cannon,” Shipley wrote according to Newsweek.

Consequently, she possesses the discretion to exclude key testimony, such as that of Trump's attorney, Evan Corcoran, if it's deemed to have breached attorney-client privilege.

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Shipley noted that Cannon has the authority to disallow the use of Corcoran's evidence, as well as “any evidence she deems was obtained in an improper manner.” Corcoran had been compelled to testify in 2023 about his involvement in a search for classified documents at Trump's Mar-a-Lago estate.

The possibility of Cannon excluding evidence obtained in ways she considers improper adds more complexity to an already contentious case. Trump is currently facing 40 federal charges related to his mishandling of sensitive materials after leaving office, to which he has pleaded not guilty.

The case also implicates Trump's former valet, Walt Nauta, and Mar-a-Lago maintenance manager, Carlos De Oliveira, both of whom have pleaded not guilty to charges including conspiracy to obstruct justice.

Liberal legal experts have voiced their concerns over the complexity Smith faces should he contest Cannon's recent directives. Cannon, however, has come under scrutiny for a series of rulings that seemingly favor the former president.

Last Tuesday Cannon handed a win to Trump, telling special counsel Smith to effectively hand over all classified materials to a jury for scrutiny, or risk a Trump acquittal by refusing to do so.

The controversy centered on Trump's defense that the Presidential Records Act grants him the authority to designate classified materials as personal property. The defense formed the basis of a motion to dismiss the charges against Trump for removing classified documents from the White House in January 2021.

Cannon's request for “competing scenarios” from both Trump's and Smith's legal teams for jury instructions about the Presidential Records Act has been also criticized, however. The request could lead the jury to lean towards Trump's interpretation or potentially result in Cannon dismissing the case, limiting Smith's options for appeal.

“Judge Cannon's bizarre ruling is yet another instance that clearly benefits Trump and demonstrates that she is in over her head as a judge,” legal expert Neama Rahmani, a former federal prosecutor, told Newsweek.

“The issue is a question of law that she should decide, not a question of fact for the jury.” Rahmani suggested that Smith is trapped between attempting to remove Cannon over this issue or risking further delays in the trial.

Judge Cannon declined to dismiss the case altogether earlier this month.

The legal imbroglio arrives at a critical juncture, as delays could push the trial past the upcoming presidential election. If Trump were to win the election before the trial concludes, he could potentially influence the Justice Department to drop the case.