Judge Aileen M. Cannon’s stunning dismissal this week of the most serious charges faced by Donald Trump put her on shaky legal ground, according to experts, who say she is on track to be reversed on appeal and could even be removed from the case — an extraordinary, but not unheard of step.
Because of the political calendar, however, any legal repercussions could be short-lived.
Trump’s alleged mishandling of classified national security records and obstruction of government efforts to retrieve the material may not matter if the former president and current Republican nominee is elected in November. If he gets back to the White House, Trump could pressure his Justice Department to close the case. He could also promote Cannon to the very appeals court that will soon examine her decision to toss the case.
Cannon’s finding that special counsel Jack Smith was improperly appointed by Attorney General Merrick Garland to investigate Trump conflicts with numerous past court decisions and the nation’s long history — during both Democratic and Republican administrations — of allowing independent prosecutors to handle high-profile instances of alleged wrongdoing.
Smith has filed notice of his plans to appeal to the U.S. Court of Appeals for the 11th Circuit, which reviews decisions from the Florida district where Cannon, a relatively inexperienced judge appointed by Trump in 2020, sits.
The court has already rebuked her twice for her handling of other aspects of the classified documents case, sending what Yale Law School professor Akhil Amar described as a message that her decisions had been “way out of line.”
The question now, Amar said, is how quickly and dramatically the appeals court acts on the latest ruling, which dismissed the entire indictment for Trump and his two co-defendants.
“They may not want to stick their head in a buzz saw if they can just let the case take its slow, deliberative course,” he said.
In her 93-page decision, Cannon said there is no specific statute authorizing the attorney general to appoint a special counsel. She also said the Constitution requires someone with Smith’s authority to be confirmed by the Senate.
The judge acknowledged the tradition of special-attorney-like figures in moments of political scandal involving high-level government officials, from Watergate to Iran-contra to Russia’s attempts to interfere in the 2016 election.
But Cannon said the practice of appointing such independent prosecutors has been inconsistent and based on a “spotty historical backdrop.” Smith, she wrote, is “a private citizen exercising the full power of a United States Attorney, and with very little oversight or supervision.”
Conservative legal groups have long questioned the constitutionality of special counsel appointments. Cannon repeatedly cited Justice Clarence Thomas, who raised the issue in a solo opinion this month as part of the Supreme Court’s decision granting Trump broad immunity from prosecution for official acts. That Supreme Court case focused on Smith’s separate election interference prosecution of Trump in D.C.
She also embraced the arguments in a law review article by Gary Lawson of Boston University School of Law and Steven G. Calabresi, a Northwestern law professor and a co-founder of the Federalist Society, with which Cannon is affiliated.
Other legal experts, however, have joined former Justice Department officials and Smith’s legal team in saying her ruling ignores the history of special counsel appointments and flouts Supreme Court precedent.
Most notably, the high court in 1974 unanimously required President Richard M. Nixon to hand over recordings to a special prosecutor as part of the Watergate investigation. In that opinion, the justices endorsed the office, citing several statutes under which the attorney general had “delegated the authority to represent the United States in these particular matters to a Special Prosecutor with unique authority and tenure.”
While lower-court judges are bound to follow the Supreme Court’s lead, Cannon took the unusual step of finding she was not required to abide by that aspect of the high court’s opinion in U.S. v. Nixon, saying the case did not directly address the validity of the office of special counsel.
Michael J. Gerhardt, a University of North Carolina law professor who teaches about constitutional conflicts between presidents and Congress, said Cannon cannot just brush aside a unanimous high court ruling.
“For a trial judge to ignore it is judicial malpractice,” he said, describing her most recent decision as part of a “pattern of bias that leads her to endorse wacky or unfounded arguments, and that’s a problem if you’re a judge.”
Until the late 1990s, authority for an independent prosecutor was found in a federal law that many analysts believed was problematic in part because it required a panel of judges to appoint the independent counsels. The law was replaced by Justice Department regulations written according to specific statutes, according to former acting solicitor general Neal Katyal, who drafted the rules in consultation with Congress when he worked for then-Attorney General Janet Reno.
Separately, the U.S. Court of Appeals for the D.C. Circuit has twice rejected challenges to the use of special counsels. First, in a 1987 opinion upholding the appointment of Lawrence Walsh to investigate the Iran-contra scandal, and more recently in 2019, upholding the appointment of former FBI director Robert S. Mueller III to probe Russian election interference and possible ties between those efforts and the 2016 Trump campaign.
Former deputy attorney general Rod J. Rosenstein, who appointed Mueller, said the fact that special counsels are accountable to the attorney general is significant. Just as rank-and-file federal prosecutors are subject to oversight in handling their assigned cases, the special counsel can be overruled by the attorney general, said Rosenstein, who also was part of independent counsel Kenneth Starr’s Whitewater trial team investigating President Bill Clinton and first lady Hillary Clinton in the 1990s.
“The Attorney General’s authority to overrule the special counsel is critical,” Rosenstein said, “because in my opinion it would be unconstitutional to make a prosecutor fully independent.”
Bruce Fein, another former high-level Justice Department official, worked in the office of legal counsel during the Nixon administration when then-acting attorney general Robert H. Bork appointed Leon Jaworski as the Watergate special prosecutor. Fein recalled deep concerns about the department’s internal ability to investigate the Nixon administration and a strong awareness of the need for independence.
Contrary to Cannon’s opinion, Fein said, the position of special counsel was specifically designed to strengthen separation of powers by preventing the executive branch from covering up its own crimes. While Garland appointed Smith to reassure the public that the investigation of Trump would be shielded from politics, Fein emphasized that Smith is still subject to oversight by the attorney general and must follow Justice Department policies and regulations.
Garland has met with Smith and the other special counsels he has appointed multiple times throughout their investigations, according to people familiar with the meetings, who spoke on the condition of anonymity to discuss them.
The appeals court has already shown skepticism of Cannon’s handling of Trump’s case in its earlier blunt reversals.
In September 2022, the 11th Circuit unanimously granted the Justice Department a reprieve from Cannon’s order barring them from reviewing documents with classified markings seized from Mar-a-Lago, Trump’s Florida home and private club. Three months later, a different 11th Circuit panel said Cannon was wrong to appoint an outside expert to decide whether any of the seized documents should be shielded from criminal investigators.
In both cases, two of the three judges on the panel were nominated by Trump.
But Cannon’s decision to appoint the special master nevertheless delayed the case — just as her dismissal of the indictment will at the very least push any possible trial past the coming presidential election. Such delays have been a primary part of Trump’s legal strategy in this and his other criminal cases.
“Everything points in one direction,” Fein said of Cannon. “She is trying to ensure that Trump cannot be tried before November in hopes that if he’s elected he’ll shut down the prosecution.”
It is not known how soon Smith will file an appeal or whether as part of it he will ask the 11th Circuit to take Cannon off the case. Such a move, while unusual, would not be unprecedented. The D.C. Circuit in 2006 removed a trial court judge from a case involving Native American oil and gas royalties, finding that the judge appeared biased against the Interior Department. It was the third time a sitting judge had been removed by the D.C. Circuit
At a hearing in her Fort Pierce, Fla., courtroom last month, Cannon acknowledged that precedent seemed to support Garland’s appointment of Smith even as she pressed prosecutors about whether there had been “any actual oversight” by the attorney general.
Less than two weeks later, Thomas issued his concurring opinion in Trump’s immunity case that called into question the validity of the appointment of Smith.
Even though the Florida indictment was not before the justices, Thomas seemed to speak directly to Cannon: “If this unprecedented prosecution is to proceed, it must be conducted by someone duly authorized to do so by the American people. The lower courts should thus answer these essential questions concerning the Special Counsel’s appointment before proceeding.”
Cannon gave her answer Monday, declaring Smith’s appointment invalid. Adding to the drama was the fact that her opinion landed on the opening day of the Republican National Convention in Milwaukee, where Trump — ear bandaged for an injury sustained during a failed assassination attempt — was feted by the party faithful before accepting the nomination.
Trump praised Cannon by name in his convention speech, referring to her as a highly respected federal judge.
Whatever the 11th Circuit decides may be appealed to the Supreme Court, which issued several notable rulings favorable to Trump this term — including the sweeping grant of immunity.
It is not clear how the justices would view Cannon’s conclusion on the special counsel issue, however. Legal experts said it was telling that no other justice joined Thomas’s separate opinion.
One justice, Brett M. Kavanaugh, has been highly critical of the now-expired independent counsel law and the Supreme Court’s decision upholding that statute. As a young lawyer, Kavanaugh was part of independent counsel Starr’s team. During oral arguments in Trump’s immunity case, Kavanaugh called the 1988 ruling known as Morrison v. Olson “one of the court’s biggest mistakes.”
But Amar, the Yale law professor, said those concerns do not necessarily translate to the separate position Smith occupies. Like Kavanaugh, Amar is critical of the former law because it required a panel of judges to appoint the independent counsel. The special counsel process avoids that problem and offers an antidote, he said, because the prosecutor is selected by the executive branch and can be fired by the attorney general.
Even as he and other legal experts predicted Cannon’s ruling would be overturned, Amar also said her legal future could be bright.
If Trump is reelected and Republicans take control of the Senate, he said, Cannon could be tapped for the appeals court or even to the Supreme Court, if there is a vacancy.
Perry Stein contributed to this report.