When Judge Aileen Cannon rejected Donald Trump’s request last month to delay his classified documents trial until after the 2024 election, it looked like there might be a small glimmer of hope. Fears that she would rule in a manner excessively favorable to the ex-president, it seemed, were unfounded. She hadn’t simply jumped when Team Trump said jump, which, given how things went the last time around, was something! But based on the proceedings that went down in Cannon’s courtroom this week, it appears that old habits, unfortunately, die hard.

On Monday, the Trump-appointed judge ordered that two sealed filings submitted by special counsel Jack Smith be struck from the record, and questioned the “legal propriety” of using an “out-of-district grand jury proceeding to continue to investigate and/or to seek post-indictment hearings.” (The filings concerned a motion brought by the DOJ arguing that an attorney for Trump aide and alleged coconspirator Walt Nauta has potential conflicts of interest because he represents other individuals who could be called as witnesses in the case.) While Cannon gave Smith until August 22 to explain the situation, legal experts immediately pointed out that (1) the reason is quite obvious, and (2) the judge’s line of questioning should be raising major red flags.

“Judge Cannon clearly shows her ignorance (bias? both?),” former federal prosecutor Andrew Weissmann wrote on Twitter. “The obstruction crimes that were investigated are charges that could have been brought in FLA or in DC and thus could be investigated in either district.” Constitutional law expert Laurence Tribe—who in September remarked that the judge was “in the tank for Trump”—echoed that Cannon “continues her dopey and constitutionally dubious usurpation of the executive branch’s investigative and prosecutorial prerogatives.” Former US attorney Joyce White Vance noted that Cannon’s actions “may tee up the issue of her fitness on the case.” Former prosecutor Glenn Kirschner opined, of Monday’s proceedings: “This has the feel of Judge Cannon acting as an advocate for the defense. Guess no one can accuse her of learning her lesson from the appellate court’s prior ruling that she abused her discretion & acted lawlessly to the extreme benefit of Trump.” (Cannon had key aspects of her Trump-related rulings overturned by an appellate court last year in a truly scathing decision.) Writing that Cannon “tried to sabotage this case at the outset,” Slate’s Mark Joseph Stern said he remains “extremely skeptical that she will permit a fair trial to take place.”

Trump was initially indicted by the Justice Department in June on 37 federal counts related to his handling of classified documents; weeks later, he was hit with three additional charges (two for obstruction and an additional one for allegedly violating the Espionage Act). Among the damning accusations in the superseding indictment was the claim that the ex-president and two of his employees attempted to “delete” Mar-a-Lago security camera footage that had been requested by the DOJ. According to the government, maintenance worker Carlos De Oliveira allegedly told a fellow employee that “the boss” wanted the server wiped, adding, “What are we gonna do?” (Trump and his coconspirators have pleaded not guilty to all the charges.)

The documents matter is, of course, far from the only legal peril Trump currently finds himself in. In addition, he is scheduled to go to trial in March over hush-money payments he made before the 2016 election; he was indicted last month by the Justice Department for his attempt to overturn the election, and he’s expected to be charged—possibly in the very near future!—for attempting to overturn the election in Georgia.

Bess Levin

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