Donald Trump must have thought all his Christmases had come at once. As federal investigators explored his alleged hoarding of sensitive documents in 2022, Aileen Cannon, a judge nominated by the former president, was assigned the case.
It wasn’t just that Trump had appointed Cannon, who has since made rulings which would appear to help his defense. It was that Cannon was from an emerging rightwing cadre of the judiciary – a cabal of conservative judges created by Leonard Leo, the ultimate Republican kingmaker and a close Trump ally.
Those links between Cannon and a network of figures and groups on the right and far-right of US politics are coming under increasing scrutiny as the Trump case moves forwards but also because they show the very real impact of Leo and his actions on the US judiciary.
Cannon rose to prominence after being handed Trump’s case in Florida, as investigators sought to gain access to boxes of documents found in his Mar-a-Lago club by the FBI. The judge, who was nominated by Trump and appointed in 2020, appointed a special master at the request of Trump’s lawyers, who was charged with vetting the seized records.
A federal appeals court later terminated the special master review, and scolded Cannon, saying she did not have the authority to prevent the justice department from accessing the materials found at Mar-a-Lago. Experts agreed.
Cannon remains in charge of the case, however, which is scheduled for May 2024. Trump was indicted in June and faces 37 federal counts, including 31 violations of the Espionage Act.
With Cannon’s profile higher than ever, her impartiality is being questioned. The judge’s financial disclosure form for 2021, which was reviewed by Accountable.US, a liberal-leaning watchdog group that tracks government corruption, shows that she was reimbursed by George Mason University’s Antonin Scalia Law School for a six day trip to “colloquium seminar” held at a resort and spa in Montana in September.
The law school was renamed after Scalia, a conservative supreme court justice in 2016 – months after his death – “the result,” the New York Times reported, “of a $30 million gift brokered by Leonard Leo.” George Mason University intended the Antonin Scalia school to become “a Yale or Harvard of conservative legal scholarship and influence”, the Times wrote.
The purpose of Cannon’s 2021 trip, according to her financial disclosure form, was to attend the “Sage Lodge Colloquium”, an annual conference held by the law school in the town of Pray, Montana. Newsweek reported that Cannon attended the colloquium again in 2022.
It is not clear why her hotel and travel was paid for. Organizations will commonly reimburse guest speakers or lecturers, but the agenda of that year’s seminar does not show Cannon doing any teaching or speaking.
Cannon was not required to state how much she was reimbursed by the law school, and there is no suggestion of any wrongdoing.
The Sage Lodge website describes the resort and spa as “the ultimate Montana luxury resort getaway”.
Seminars at the 2021 event terminated at 12.15pm each day. One class included “Woke Law!”, which was taught by Todd J Zywicki, a professor at George Mason University Antonin Scalia Law school and a senior fellow at the Cato Institute, a thinktank founded by the Koch brothers.
There is no suggestion that Leo, who has worked as an adviser to Trump and is seen as the one of the most influential conservative activists in the US, directly funded the trips. But his influence runs so deep in conservative circles that other ties also exist between him and Cannon.
She has been a member of the conservative Federalist Society, which Leo co-chairs, since 2005. The society, its website states, is “a group of conservatives and libertarians dedicated to reforming the current legal order”.
The Federalist Society’s profile of Leo, who has come under scrutiny for reportedly directing tens of thousands of dollars to the wife of supreme court justice Clarence Thomas, boasts of his influence over the upper echelons of the American judicial system.
“Leonard has advised President Trump on judicial selection, assisted with the Gorsuch and Kavanaugh supreme court selection and confirmation process,” the Federalist Society profile reads.
“He also organized the outside coalition efforts in support of the Roberts and Alito US supreme court confirmations.”
Those efforts have had striking ramifications, none more so than the supreme court’s decision to overturn Roe v Wade, which guaranteed the right to abortion in the US, last year.
“Leonard Leo has written the playbook on judicial influence-peddling. It’s no surprise that Judge Cannon has benefited from Leo’s well-funded network,” said Kyle Herrig, senior adviser at Accountable.US. “Over decades, Leo has used shady tactics to curry favor with judges at all levels in service of his ultimate goal: to force an extreme, radical agenda on Americans.”
Leo, Politico reported, has also been responsible for the installation of “dozens of lower court federal judges across the country”.
Since Cannon has taken control of Trump’s case, legal experts have voiced concerns she could slow down the trial, which could benefit Trump. Last month, however, Cannon rejected the Trump team’s request to delay trial until after the November 2024 presidential election, although her decision to hold it in May also disappointed government prosecutors, who had requested a December 2023 start date.
Questions surrounding her handling of the trial are unlikely to go away, however, given her links to the Leo-dominated Federalist Society and the Leo-aided Antonin Scalia law school.
“Ultimately it calls into question the judge’s impartiality and who she’s serving,” Herrig said.
“Is she serving the American people or is she serving Leonard Leo and the Federalist Society.”
