Aileen Cannon and Tanya Chutkan: What to know about the judges in Trump’s federal trials

The courts have randomly assigned two very different judges to oversee former President Donald Trump’s upcoming federal criminal trials.

In Washington, D.C., where Trump faces charges of conspiring to overturn his loss in the 2020 presidential election, District Judge Tanya Chutkan, a Barack Obama appointee, is running the show.

In Florida, where Trump has been indicted for hoarding classified documents, District Judge Aileen Cannon, a Trump appointee, is at the helm.

Guess which judge the defendant prefers.

“I’m very proud to have appointed her,” Trump gushed about Cannon last month. “She’s very smart and very strong, and loves our country. We need judges that love our country so they do the right thing.”

As for Chutkan, Trump has been more … critical. “There is no way I can get a fair trial with the judge ‘assigned’ to the … case,” he posted Sunday on Truth Social. “Everybody knows this, and so does she! We will be immediately asking for a recusal of this judge on very powerful grounds.”

Even though experts say Trump’s demand that she be recused is meritless — and his own lawyers have signaled that they agree — the former president and his allies are certain to keep pleading his case in the court of public opinion. (Chutkan will rule Friday on special counsel Jack Smith’s request for a protective order to prevent Trump from “publicly targeting individuals.”)

Politics aside, which judge is actually more likely to preside "fairly," that is, by neither opposing nor favoring Trump? Here are the facts so far.

Age

Chutkan: 61 years old

Cannon: 42 years old

Education

Chutkan: George Washington University (BA); University of Pennsylvania (JD)

Cannon: Duke University (BA); University of Michigan (JD)

Prior experience

Chutkan: More than a decade serving as a court-appointed public defender in D.C., followed by another decade at the white-shoe law firm Boies Schiller & Flexner, where she focused on complex civil litigation.

Cannon: Three years as an associate at the D.C. office of the corporate law firm Gibson Dunn, followed by seven years as a prosecutor for the Southern District of Florida, where she worked in the major crimes and appellate divisions.

Political affiliations

Chutkan: Donated $1,500 to Barack Obama's campaign between 2008 and 2009; donated $250 to Kirsten Gillibrand’s Senate campaign in New York in 2008.

Cannon: Registered Republican; member of the conservative/libertarian Federalist Society; donated $100 to Ron DeSantis's gubernatorial campaign in Florida in 2018.

Details of confirmation

Chutkan: A 95-0 vote in the U.S. Senate in 2014; the American Bar Association rated her “Unanimously Qualified” for the position.

Cannon: A 56-21 vote in the U.S. Senate in 2020; the American Bar Association rated her as "Qualified" for the position.

Number of criminal trials overseen

Chutkan: According to the Court Listener database, she has been assigned 1,810 cases and issued opinions in 616 of them — 18 of which dealt with criminal charges. The Associated Press reports that Chutkan has also sentenced at least 38 people convicted of Jan. 6 riot-related crimes. She testified during her Senate confirmation process that she had tried “approximately 40 to 45 cases to verdict or final decision” as an attorney, adding that she was a lead defense lawyer in many involving “serious felonies, such as homicide, first-degree sexual assault and kidnapping.”

Cannon: She has been assigned 224 criminal cases — four of which went to trial, according to a New York Times review. Each was a “relatively routine matter,” the Times reported, including accusations of possession of a gun by a felon, assaulting a prosecutor, smuggling undocumented migrants and tax fraud. The four matters generated between two and five days of trial each, for a total of 14 trial days. As a prosecutor, Cannon previously helped secure the convictions of 41 defendants, including four from jury trials.

Related rulings

Chutkan: In 2021, she rejected Trump's efforts to block the congressional Jan. 6 committee from accessing his White House records, delivering a swift rebuke on the limits of invoking executive privilege as an ex-president.

“Presidents are not kings,” she wrote, “and plaintiff is not president.” Trump appealed Chutkan’s decision to the U.S. Supreme Court, which ruled against him by an 8-1 margin.

Cannon: Last year, she oversaw a civil lawsuit filed by Trump after the FBI searched his Mar-a-Lago estate in Florida and seized more than 100 classified documents he had kept in defiance of an earlier subpoena.

According to the New York Times, Cannon “blocked investigators from access to the materials, imposed a special master to vet the files for any that should be permanently kept off limits, entertained the unprecedented idea that some White House files could be kept from criminal investigators in the Justice Department under executive privilege, and set a calendar that threatened to all but freeze the inquiry for at least four months.

“Her opinions,” the Times explained, “suggested that a former president should receive greater protections than an ordinary criminal suspect.”

Controversies

Chutkan: She has drawn attention for imposing tough sentences on Jan. 6 rioters, matching or exceeding prosecutors’ recommendations in 19 of her 38 cases to date. (Other D.C. district judges have typically been more lenient.) “It has to be made clear that trying to violently overthrow the government, trying to stop the peaceful transition of power and assaulting law enforcement officers in that effort is going to be met with absolutely certain punishment,” Chutkan said in December 2021.

Cannon: Her previous pro-Trump decisions were widely criticized and quickly overturned by a conservative appeals court, with a three-judge panel (including two fellow Trump appointees) ruling that she had “improperly exercised equitable jurisdiction, and that dismissal of the entire proceeding is required.”

“The law is clear,” the appeals panel wrote. “We cannot write a rule that allows any subject of a search warrant to block government investigations after the execution of the warrant. Nor can we write a rule that allows only former presidents to do so. Either approach would be a radical reordering of our caselaw.”

Cannon went on to reject Trump’s request last month to delay the documents trial until after the 2024 election. Yet experts have subsequently questioned her decision earlier this week to strike two of Jack Smith’s conflict-of-interest filings from the record, while forcing him to justify his ongoing D.C. grand jury investigation.

Meanwhile, an Aug. 4 report from Reuters discovered that Cannon “made two errors in a June trial, including one that potentially violated the defendant's constitutional rights and could have invalidated the proceedings.”