A tale of two judges: How a pair of women are navigating Trump’s blockbuster federal trials

A soft-spoken former prosecutor residing in South Florida and a quippy onetime public defender based in Washington, D.C., share a rare commonality. They are overseeing completely different but equally consequential criminal trials involving a former and possibly future president.

Aileen Cannon, a Colombia native who grew up in Miami, is a longtime member of the conservative Federalist Society and was appointed to the federal bench by former President Donald Trump in 2020.

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Tanya Chutkan, who was born in Jamaica, is a former President Barack Obama appointee who donated thousands of dollars to him beginning in 2008. She assumed her role as a district court judge in 2014.

Since taking on cases featuring Trump as the criminal defendant, the pair have drawn enormous scrutiny. Headlines have questioned Cannon’s experience level and Chutkan’s impartiality.

Trump has publicly opined on the two, calling Cannon “very highly respected” and Chutkan a “biased Trump-hating judge.”

The pair also work in districts that will pull from very different jury pools for Trump’s trials. While southeast Florida leans blue, Washington is one of the bluest regions in the country. Trump received about 5% of the vote in its 2020 election.

By all appearances, Trump should fare better in his trial in Florida. A string of pretrial orders issued by the judges supports that notion.

But the cases are so different that to reduce them to the political leanings of their judges and venues would be to miss key elements of them.

Cannon has indeed issued more orders that are favorable to Trump, but her case deals with what she has described as an “unusually high volume” of evidence — and any that is classified requires added attention pursuant to the Classified Information Procedures Act.

Special counsel Jack Smith alleges in the Florida case that Trump willfully retained national defense information. Trump is charged with felonies under the Espionage Act, and the indictment paints a picture of Trump recklessly storing boxes filled with national secrets in a bathroom and ballroom of his Mar-a-Lago residence when he left office before attempting to hide some of the boxes from federal investigators. Trump has pleaded not guilty to the charges.

The case is playing out under CIPA, which requires parties to go through weekslong phases of weeding out and organizing classified discovery ahead of trial.

In perhaps her most consequential ruling, Cannon granted Trump extensions on CIPA filing deadlines last month and said parties could reassess subsequent deadlines in the case during a March 1 conference call.

The trial is scheduled to begin in May, but Cannon’s decision almost certainly guarantees the trial will be delayed for months. This was a clear victory for Trump, the leading GOP presidential contender, who has been aiming to delay his trials until after the 2024 election.

“Defendants need more time to review the discovery in this case,” Cannon wrote of her decision. “This Order aims to afford that opportunity in a reasonable fashion, balanced against the public’s right to a speedy trial.”

It is possible that Cannon is more sympathetic to Trump than other judges would be, but discovery in the case involves more than a million pages of unclassified and classified documents, as well as security footage that spans months. Delays may not just be desirable for the defense but also practically necessary.

Chutkan has not awarded Trump such relieving delays in Washington, but discovery in that case is also not subjected to classified material mandates.

Smith charged Trump in that case with illegally conspiring to overturn the 2020 election and to obstruct an official proceeding, and Trump has pleaded not guilty to those charges.

The subject matter in the case is highly polarizing, often referencing the Jan. 6 riot and Trump’s persistent claims that the 2020 election was rife with fraud.

Exacerbating matters is Chutkan’s experience with the Jan. 6 riot suspects. She has overseen more than two dozen cases featuring defendants who faced charges similar to Trump’s and has gained a reputation for handing out harsh sentences.

She once took issue during a Jan. 6 defendant’s hearing with the “blind loyalty” riot participants showed to Trump rather than the Constitution and pondered aloud how Trump “remains free to this day.”

Trump used this as part of his argument that Chutkan should recuse herself from the case, but Chutkan rejected his request.

“The statements certainly do not manifest a deep-seated prejudice that would make fair judgment impossible,” Chutkan wrote in her decision.

The topic at hand and Chutkan’s background naturally have invited more of Trump’s scorn than the case in Florida, which also led to perhaps Chutkan’s most high-profile move thus far: granting Smith a gag order request.

The order banned parties in the case from making public statements that “target” Smith or his staff, defense attorneys or their staff, court staff, and “any reasonably foreseeable witness or the substance of their testimony.”

After Trump argued this violated his free speech rights, an appeals court narrowed the order to exclude Smith.

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Chutkan has also denied Trump’s motions to dismiss the case, but those are going through the appeals process, and Chutkan made an expected but Trump-friendly decision to stay all proceedings in the case indefinitely while higher courts review Trump’s motions.

Chutkan had kept a diligent schedule intact during the case and had even begun preparing for jury selection ahead of the anticipated March 4 trial start date, but Chutkan’s decision to halt the case means that the start date may no longer be realistic.