Klasfeld’s reporting is part of Just Security’s Trump Trials Clearinghouse.

Over the course of two days of oral arguments, former President Donald Trump’s attorneys aimed at the 150-year-old foundations of the practice of appointing special counsels in the United States. The first day of arguments appeared to put Trump’s attorneys largely on the defensive. 

Then, Special Counsel Jack Smith’s assistant appeared concerned that the judge was seriously considering Trump’s attack against their pot of “permanent, indefinite appropriations” from which they draw their financing. Such a challenge could force prosecutors to draw from another source within the Department of Justice, or face dismissal. Prosecutors emphasized that they have other funds to sustain the case.

Whether or not Trump ultimately prevails in challenging Smith’s constitutional authority to prosecute him, his defense may have come closer to achieving other goals over two days of oral arguments. 

The first, and most frequently discussed, is delay. 

U.S. District Judge Aileen Cannon has already indefinitely postponed Trump’s trial for alleged Espionage Act violations over his possession and retention of classified documents at the Mar-a-Lago resort, and this multi-day hearing over a longshot legal challenge has only pushed his reckoning in the case further off on the calendar. 

As an added bonus for Trump, this delay comes in the form of conversation his lawyers want to keep in the public eye: Attorney General Merrick Garland’s role in supervising the special counsel and the money that funds Smith’s prosecution. 

As for the broader battle, Trump’s overarching effort to declare Smith unconstitutionally appointed remains a longshot, but Cannon made a blockbuster remark on Monday suggesting that the “limitless” funding of the special counsel’s office implicates serious separation of powers concerns for her. 

The Long and Storied History of Special Counsels in the United States

During the first day of arguments, prosecutor James Pearce noted most of the courts agree with the special counsel: Eight judges unanimously rejected the notion that attorneys general lack the power to appoint special counsels in four separate criminal cases. Moreover, the U.S. tradition of special prosecutors dates back roughly a century and a half to then-President Ulysses S. Grant in the 1870s, and though the forms and practices of these appointments have varied, never once has a judge considered them unconstitutional. 

During the Watergate era, the Supreme Court unanimously signed off on the special prosecutor’s authority in ordering then-President Richard Nixon to turn over the subpoenaed tapes in 1974. Nixon did not dispute the special prosecutor’s authority, leading to enduring debate on whether the Supreme Court resolved a contested issue, but every subsequent criminal defendant who tried to treat that as a source of controversy failed. Special Counsel Robert Mueller successfully fended off attacks on his authority by Trump’s former campaign manager, Paul Manafort, Roger Stone’s associate, Andrew Miller, and Concord Management, the Russian company behind what prosecutors described as the internet troll farms engaged in attacks on the 2016 presidential election. 

More recently, President Joe Biden’s son Hunter unsuccessfully fought the constitutional authority of Special Counsel David Weiss. 

Despite attempts by Trump’s attorneys to draw distinctions between those cases, Cannon appeared reluctant to buck this tradition, and she rebuked Trump’s attorney Emil Bove for likening a special counsel to a “shadow government.” 

“That sounds very ominous: shadow government, but what do you really mean?” Cannon pointedly asked Bove, fresh off a stinging defeat in Trump’s New York criminal trial.

When Bove argued there was a risk in appointing someone with as much power as a special prosecutor without Senate confirmation, Cannon questioned whether that concern was “realistic” given the “well-defined regulations” surrounding these appointments.

“I don’t know if it’s really fair to throw aspersions in that direction,” Cannon said. 

Trump’s Defense Strategy: Ratchet Up ‘Tension’ at Heart of the Special Counsel’s Role

In all four of his criminal cases, Trump’s defense strategy has involved casting aspersions on prosecutors as partisan tools of President Biden. 

Trump’s attorneys have not actually shown any ties between Biden and the special counsel — or for that matter, two local district attorneys in New York City and Atlanta over whom the White House has no jurisdiction. In Trump’s federal election interference case related to the Jan. 6th attacks, Smith’s prosecutors emphasized that there’s “no coordination” between them and the Biden administration, and Garland’s remarks when appointing a special counsel suggested that this was the point.

“Such an appointment underscores the Department’s commitment to both independence and accountability in particularly sensitive matters,” Garland declared over a year and a half ago, on Nov. 18, 2022. 

Trump’s attorney Bove tried to use these words against Smith, pointing out that the U.S. Constitution requires the Senate’s advice and consent on appointees who aren’t “inferior officers.” 

If Smith doesn’t ultimately report to Garland, Bove argued, that would make the special counsel an unconfirmed “superior officer.” 

Pearce countered that all that matters in terms of the Constitution and precedent is that Garland has the power to supervise or even shut down the special counsel’s investigation. He declined to provide any details about what supervision Garland actually has over the investigation, including whether the attorney general signed off on Trump’s indictment. 

Toward the end of the five-hour hearing on the first day, Cannon pressed Pearce to answer that question — and asked why such a disclosure would give prosecutors “heartburn.” 

The Justice Department has not yet revealed whether Smith reported to Garland before Trump’s indictment, and Pearce declined to solve the mystery at the hearing. 

The prosecutor did, however, provide a strong indication about the answer, noting that the Code of Federal Regulations requires special counsels to notify an attorney general of any “significant events.”

Due to Justice Department practices, Pearce would not put on the record whether the history-making federal indictment of a former U.S. president amounted to a “significant event.” The prosecutor’s lack of a “yes” or “no” answer also averted a potentially major headline.

Trump Defense ‘Flip-Flopped’ on Special Counsel in Funding Attack

In questioning Smith’s funding, Trump’s legal team took the opposite tactic: Bove argued that, if Smith is in fact accountable to Garland under well-established regulations promulgated by former Attorney General Janet Reno, then the special counsel is insufficiently “independent” to benefit from a permanent and indefinite appropriation. 

On Monday, Cannon called out what she described as the “tension” between the two arguments.

“You’re saying the special counsel is taking inconsistent positions, but aren’t you just doing the same thing, flip-flopped?” the judge asked.

When responding to the argument, Pearce acknowledged neither side staked out a fully consistent position.

“I think that’s true of both sides of this matter,” Pearce said.

But Pearce added that was inherent in the special counsel’s role — and how Reno designed the regulations with an eye toward “striking the right balance between accountability and independence.”

However, Cannon appeared troubled by the “limitless” nature of the appropriations, in the wake of the Supreme Court’s recent ruling in Consumer Financial Protection Bureau v. Community Financial Services Association of America, Limited. She noted that the Court found the appropriations clause authorizes the CFPB to draw public funds from a particular source ”in an amount not exceeding an inflation-adjusted cap.” Smith’s funding has no cap at all. 

Performing an on-the-spot audit of the special counsel, Cannon took out one of Smith’s disclosures in court and asked for clarification. 

Pearce urged Cannon to allow for further briefing if she is seriously considering granting Trump’s motion, and he said that the Justice Department is prepared to replace their appropriation from a separate $1 billion pool in their budget. He also emphasized the prosecution’s view that precedent and tradition favors them. Roger Stone and Hunter Biden both failed in attacks on the special counsel’s funding, though those cases are not binding on Cannon’s jurisdiction, and were decided before the Supreme Court’s ruling upholding the CFPB’s funding scheme. Eight special counsels have drawn from permanent and indefinite appropriations, all without incident and with “congressional acquiescence,” Pearce noted.

“The doctrine of congressional acquiescence is not the most robust doctrine,” Cannon countered.

Trump’s attorneys, for their part, appear ready to exploit any tension they have ginned up through their challenge to Smith’s authority. On Monday afternoon, Cannon will hear arguments on whether to limit Trump’s ability to comment on the case. Last month, Trump  falsely claimed that the FBI was authorized to shoot him during its search of Mar-a-Lago. Bove questioned whether Garland signed off on that search warrant request, as well, and if prosecutors must finance the case from another pool, Bove indicated there may be a political fallout. 

Cannon declined to issue a decision from the bench by the time of publication.

Cannon Hits a Crossroad

As she considers her ruling, Cannon may have good reason to avoid straying too far out of step from her peers and tradition, particularly with potential appeals of any decision on the horizon, a process which has not turned out well for her thus far.

In the investigation predating Trump’s first federal indictment, the 11th Circuit reversed Cannon’s decision to block prosecutors from using certain evidence for their active investigation pending a review of the files the FBI seized for attorney-client privilege and executive privilege. Two of the judges who unanimously reversed her in the scathing ruling were also Trump appointees. That background, along with several of Cannon’s pre-trial decisions since that time, have amplified concerns about her experience and apparent deference to the president who appointed her. Cannon’s appointment rushed through the Senate along partisan lines during Trump’s lame-duck session. 

On the cusp of the hearings, the New York Times published an extraordinary account of how Cannon insisted on keeping the case assigned to her docket, over the advice of two senior judges from her district. According to the Times, one was the Southern District of Florida’s Chief Judge Cecilia M. Altonaga, a George W. Bush appointee. The other was unidentified. The article did not articulate these judges’ concerns, though they presented perceptions of Cannon’s bias and her relative inexperience as context. Some legal analysts, like former FBI general counsel Andrew Weissmann, have opined that another reversible ruling would hand prosecutors an attempt to try to disqualify her from the case, or simply pass off the indictment to the Southern District of Florida, for reassignment to another judge. 

The structure of the hearing itself stoked a separate controversy: Cannon scheduled two days of arguments over an issue widely viewed in the legal community as Trump’s moonshot. What’s more, the judge signaled a willingness to consider that challenge seriously by allowing third parties to weigh in on the matter. 

Those supporting Trump’s attack on the special counsel’s authority include a broad array of conservative figures and groups, including Citizens United, the group whose attack on Hillary Clinton produced the watershed Supreme Court campaign finance ruling; the Landmark Legal Foundation, and right-leaning attorneys Steven Calabresi, Seth Barrett Tillman, former U.S. Attorney General Edwin Meese III, and former federal judge Michael Mukasey. More than a dozen scholars and the group State Democracy Defenders Action oppose the motion, and their legal brief notes how rare it is for any third parties — for or against Trump — to have a hearing during pre-trial proceedings in a criminal case at all. 

Citing the website Empirical SCOTUS, Trump’s opponents represented by attorney Matthew Seligman pointed to Supreme Court data for reference. From 1980 through 2015, SCOTUS permitted non-governmental third parties to participate in only nine out of 4,045 oral arguments as amicus curiae. Political groups weighing in on pre-trial hearings on a trial court level are even more unusual. 

Recently, Cannon appears to have pulled up the drawbridge for amicus filings. She rejected a series of similar requests by a group of Republican attorneys general and a pro-Trump advocacy group affiliated with the former president’s adviser Stephen Miller.

Whether this represents a shift in Cannon’s handling of the case remains to be seen, and she did not immediately rule on the issue before her. Legal observers will be sure to closely watch not only how she rules, but also the timing of her decision and how it addresses Trump’s broader effort to delegitimize the special counsel appointed to prosecute him.

IMAGE: The Alto Lee Adams Sr. United States Courthouse, where U.S. District Judge Aileen Cannon is holding a hearing regarding former President Donald Trump on May 22, 2024, in Fort Pierce, Florida. (Photo by Joe Raedle via Getty Images)