Trump is poised to bypass his legal woes thanks to judges he appointed

Donald Trump is on the cusp of emerging unscathed from his four criminal prosecutions — thanks almost entirely to the decisions of four judges he appointed.

Trump’s three Supreme Court picks formed a decisive bloc to declare presidents immune from prosecution for official conduct — freezing the charges he faces in multiple jurisdictions for trying to subvert the 2020 election and putting his New York conviction in doubt. Then his nominee to the federal court in Florida, Judge Aileen Cannon, handed him another victory by dismissing the charges he faces for hoarding classified documents and concealing them from investigators.

Her decision earned a shout-out from Trump as he accepted the Republican nomination on Thursday. “A major ruling was handed down from a highly respected federal judge in Florida, Aileen Cannon,” he said.

Trump’s string of victories reflects what experts say is extraordinary luck and timing. He’s the first president since Ronald Reagan to appoint three justices to the Supreme Court, and the first to ever face criminal charges that, soon thereafter, landed in front of the very judges he put on the bench.

“This is a perfect example of serendipity, how the occurrence of events and trials and tribulations of the judicial process have all combined to work in favor of Donald Trump,” said Gene Rossi, a former federal prosecutor and civil litigator.

But it’s also a function, those experts say, of the fact that Trump rose to power in an era when conservatives — who had been burned in the past by judicial picks that later broke ranks — had begun perfecting a strategy of appointing judges who would more reliably rule in their favor. President Joe Biden, too, has appointed judges whose backgrounds appear more reliably liberal, though it’s not yet clear whether he will have the same impact on the judiciary as his predecessor.

“Today, given that politics are so important in securing a judicial appointment, I can see how that sort of concern can spread,” said David Zaring, professor of legal studies from the Wharton School of Business. “[Trump] got so lucky — people don’t usually get a chance to appoint three justices to the Supreme Court in one term. Trump got it and then the Supreme Court gave him a very favorable ruling after that.”

Cannon’s ruling in the documents case had nothing to do with the substance of the charges — widely considered to be the most clear-cut case Trump faces. Cannon found that Attorney General Merrick Garland overstepped his authority when he named Smith special counsel, invalidating the entire prosecution. But the decision — which legal experts suggested would likely be reversed on appeal — nevertheless put Trump’s already-slim odds of facing trial this year effectively out of reach.

“Given her record in this prosecution so far, I can see why people would think that … she’s in the bag for the man who appointed her,” said Zaring, who said he sees some merit and conservative thinking behind the ruling, even though he views it as likely to be overturned. “Unfortunately, I think it’s going to be impossible to avoid people coming to that conclusion.”

Cannon, in particular, represents a stark example. She was confirmed to the bench in November 2020, days after Trump lost reelection to Joe Biden. And she drew widespread criticism two years later after she slowed the investigation by granting a longshot push by the defense to require that an independent monitor review materials the FBI seized from Mar-a-Lago.

A conservative appeals court panel, which featured two Trump appointees, ultimately rebuked Cannon and unfroze the case, but the delay aided defense efforts to postpone the case, part of Trump’s broader strategy to push his criminal cases past the 2024 election.

“Talk about pure luck,” said University of Massachusetts Dartmouth political science professor Kenneth Manning, who studied Trump trial court judges for a 2020 paper “They drew an inside straight when they had Aileen Cannon. When the federal prosecutors chose to charge him in Florida instead of D.C.”

To Trump’s defenders, the favorable rulings by his own judges are a sign of their willingness to make unpopular — but legally correct — calls.

“The judges appointed by Trump are ruling in his favor. The judges appointed by Democrats are going against him,” said Tim Parlatore, who has represented the former president at. “It does correctly undermine the public’s trust in the system because sometimes judges do things that are political.”

Parlatore said he largely agreed with the decisions the Trump-appointed judges are making but said the system would function better if it wasn’t so easy to predict outcomes based on the party of the president who appointed them.

Not all of Trump’s appointees have ruled uniformly in his favor throughout his yearslong odyssey through the criminal justice system. In 2022, the Supreme Court rebuffed his effort to shield his White House papers from the Jan. 6 select committee, and it declined to consider his Cannon-backed effort to keep the documents investigation frozen.

Before Trump left the White House, several of his own appointees issued fierce rebukes of his and his allies’ efforts to overturn election results in a handful of swing states. And one of Trump’s appointees, U.S. District Judge Dabney Friedrich, issued a key ruling that upheld the validity of special counsel Robert Mueller’s appointment — a decision that now stands in contrast to Cannon’s conclusion about Smith. But that willingness to buck party lines may be an increasingly rare phenomenon.

Zaring, the Wharton professor, studied Trump’s appointees to the appellate court and found that they were younger, far likelier to have worked in political jobs or the White House and had “a ton of exposure to the conservative legal establishment.

“I just don’t think it used to be that way,” he said. “Unfortunately,” Zaring said. “I think that both Democratic and Republican presidents have been very good at seeking ideologically compatible appointees to the judiciary.”