Trump Judge and Obama Judge Have Been Surprisingly Aligned In Their Rulings on the Former President’s Legal Troubles

Two federal judges decisively rejected Donald Trump’s attempts to slow-walk his criminal trials until long after the 2024 election — but only one of them stoked the former president’s outrage.

Trump’s campaign praised U.S. District Judge Aileen Cannon for her “extensive schedule,” after she set a trial date in his classified documents case for May 20, 2024, an emphatic rebuke of his defense team’s request for an indefinite delay. 

When U.S. District Judge Tanya Chutkan slated his election-interference trial for March 4, 2024, Trump attacked her as “biased” for denying his defense team’s request to delay the case for two and a half years.

Cannon is a Trump appointee and Chutkan was a Barack Obama appointee. But when it comes to legal procedure, both judges have been surprisingly aligned so far on the ex-president’s actions, even if the reaction to them has been discordant.

“Whether it’s Donald Trump himself or his attorneys, they to date have perceived Judge Cannon as being somebody who wants to help them, and they are concerned about offending her in a way that they are not concerned about offending Judge Chutkan,” former federal prosecutor Mitchell Epner told The Messenger. 

“I think that is to their great peril,” Epner, now a partner at Rottenberg Lipman Rich PC, added, noting that personally antagonizing federal judges rarely makes for good legal strategy.

‘By the Book’

What’s more, experts have noted that Cannon and Chutkan’s early rulings have been more alike than different. 

Those inclined to view Cannon as a MAGA loyalist and Chutkan as an arm of President Joe Biden’s administration might view that skeptically, but the similarities between their actions to date are a matter of public record. 

Both issued similar protective orders, laying out the ground rules for handling evidence before trial. Both rejected efforts by prosecutors to file documents under seal, arguing for transparency over the cases. Both announced in their first public hearings that they wanted to keep politics out of the courtroom, and both prepared for trials in early 2024, far earlier than the post-election dates Trump demanded.

For Florida-based attorney David Weinstein, who frequently litigates in the same judicial district as Cannon, there has been no clear partisan divide since Trump’s federal indictments.

“It seems pretty by the book for both of them with regard to rulings,” Weinstein told The Messenger.

Unlike Supreme Court justices, who are the final arbiters of statutory interpretation, trial judges must obey higher court precedents within their jurisdictions. Weinstein noted that the high court’s frequent party-line rulings might obscure the fact that lower court judges operate within these constraints.

This trend could change as Trump’s election-subversion and classified documents prosecutions proceed to trial in March and May of next year, respectively. Trump likely will try to dismiss both cases, limit the evidence the juries may see, discredit the government’s witnesses and attack the historic felony charges as a political prosecution. More daylight may emerge between Cannon and Chutkan’s actions as they resolve these controversies.

‘A Favorable Venue’

Trump may be holding his fire on Cannon, and lashing out at Chutkan, because of their different histories and backgrounds, legal experts noted. 

“It’s clear to me, at least from watching what’s been going on, that both Trump and his legal team view Cannon as a favorable venue and view Chutkan, for whatever reason, as an unfavorable venue for them,”said Weinstein, a former federal prosecutor from the Southern District of Florida. 

Cannon, a one-time registered Republican born in Colombia, is a longtime Federalist Society member who once donated to the gubernatorial campaign of Ron DeSantis and rose to the bench during the twilight of Trump’s presidency on Nov. 12, 2020. 

Days after the announcement of Biden’s victory, Cannon stood among more than a dozen Trump nominees rushed to confirmation as the former president attacked the election results. Each of those nominees inspired contentious opposition from Democratic senators, and Cannon was no exception, becoming a federal judge in a 56-21 vote. On the day of Cannon’s confirmation, Senator Dianne Feinstein, D-Calif., called for the Judiciary Committee to stop seating Trump appointees during the lame-duck session.

Chutkan, a Black woman, inspired much less controversy when then-President Barack Obama nominated her. She cut her teeth in the public defender’s office, worked her way through major law firms, and though she has now been cast by Trump as an anti-MAGA villain, she ascended to the judiciary in an unobstructed gust of bipartisan approval. Her nomination sailed through her confirmation without opposition in a 95-0 vote in 2014.

Now handling two of the most controversial and consequential cases in U.S. history, both judges have been vilified in the public sphere. Both have received threats against them, including ones serious enough to lead to indictments. 

Early in her tenure, Cannon had two major Trump cases land on her bench by random assignment, both threatening the legacy and freedom of the man who just handed her a lifetime appointment. The rookie judge quickly courted controversy over her handling of the investigation that preceded Trump’s indictment. She temporarily blocked the FBI last summer from using the classified documents seized from Mar-a-Lago in their investigation of Trump. 

A three judge panel from the 11th Circuit, consisting of two Trump appointees and a George W. Bush appointee, struck down Cannon’s ruling as a “radical” departure from precedent limiting court involvement in criminal investigations. Legal analysts called her too deferential to the man who appointed her, a reputation she’s struggled to play down after Trump’s criminal case landed on her docket by random assignment. 

Even though the Florida trial starts two months later than the D.C. one, Weinstein noted that’s not surprising. Trump’s former case involves classified documents, three defendants and 41 counts, and the latter has him as the sole defendant in a four-count indictment, in a case where prosecutors say they will not introduce classified evidence.

‘The D.C. Case Is Really About His Legacy’

There’s little mystery why Trump would be unhappy that his election-obstruction case landed in Chutkan’s court. She is known for harshly punishing convicted Jan. 6 rioters, handing down prison sentences longer than prosecutors requested. Before sentencing ex-Ohio school employee Christine Priola, Chutkan criticized her for her “blind loyalty” to “one person who, by the way, remains free to this day.” 

That quote circulated around MAGA-friendly social media before making its way to Trump.

“She obviously wants me behind bars,” Trump wrote on Truth Social on Aug. 14. “VERY BIASED & UNFAIR!” 

Whether or not the former president’s attorneys ultimately seek her recusal, Trump and his supporters claim that Chutkan’s remark when sentencing Priola shows her advocating for his incarceration, but the judge never made such a remark directly. 

At the time of Priola’s sentencing, Chutkan observed, scores of criminal defendants in Jan. 6 cases explicitly asserted Trump inspired them to take their actions — and they were the ones going to prison for it. 

Like Cannon, Chutkan also has prior experience presiding over one of Trump’s cases, having previously shut down his attempt to block records sought by the House Select Committee investigating the Jan. 6 insurrection. 

Rejecting his claim of executive privilege, Chutkan told then-private citizen Trump: “Presidents are not kings, and Plaintiff is not President.”

Trump’s former White House attorney Ty Cobb pointed out another reason the former president may be so eager to try to discredit Chutkan rather than Cannon: Chutkan’s case is more important for the history books.

“I think Trump recognizes that the D.C. case is really his legacy,” Cobb told The Messenger. “The Mar-a-Lago case involves serious crimes, no question, but it’s not up there with defiling the Constitution in an effort to steal an election. That’s what Trump’s going to be remembered for.”

‘My Judges’

During his presidency, Trump called his appointees “my judges,” expecting their loyalty, and angrily denouncing those that do not provide it. 

He also routinely criticizes judges who rule against him, including Manhattan Supreme Court Justice Juan Merchan, who is presiding over the former president’s hush-money prosecution; U.S. District Judge Lewis Kaplan, who presided over E. Jean Carroll’s rape lawsuit against him; U.S. District Judge Gonzalo Curiel, who presided over a case involving Trump University; and several others.

And when the Supreme Court of the United States, his judicial appointees, and dozens of other judges ruled against his efforts to overturn the election, Trump swung broadly at them, too.

“The Supreme Court really let us down,” Trump wrote in December 2020, after the high court rejected an election challenge by his allies in Texas. “No Wisdom, No Courage!”

Trump appointed three of the nine justices, but none of them noted a dissent in that case. Several of his own appointees at the trial court level rejected his last-ditch election litigation before that point, but that hasn’t stopped Trump from dividing the judiciary between his loyalists and everyone else. 

This inclination could backfire at the lower court level, where judges must interpret the law in accordance with appellate and Supreme Court precedent on criminal law. 

As for their political affiliations, Epner said that under normal circumstances: “They should not matter at all,” but Trump’s perception that they do may inform his litigation strategies in all four of his cases.