Judges have looked unfavorably upon Trump in First Amendment cases this year

By Devan Cole, CNN

(CNN) — As the Trump administration faces backlash over officials’ decisions to target speech with which it disagrees, federal judges have already left a lengthy trail of rulings lambasting the government for trampling over the First Amendment rights of elite law firms, news organizations, unions and others.

The rulings underscore how judges have pushed back this year on President Donald Trump’s effort to test the durability of the First Amendment as he seeks to expand executive power in his second term. They could serve as a warning as officials open a new front in their First Amendment stress test in the wake of the assassination of conservative activist Charlie Kirk.

But even as courts side with some Trump foes in court, experts warn that the president’s playbook may be more about intimidating Americans and companies than pushing winning legal theories.

The latest judicial broadside came earlier this month when a federal judge in Boston sided with Harvard University in its effort to restore more than $2 billion in federal research funding that was frozen by the White House earlier this year.

That ruling from Judge Allison Burroughs was a stinging rebuke of the administration’s attempt to unleash the funds so long as the school allowed the government to meddle in its affairs. Burroughs, an appointee of former President Barack Obama, rejected claims by the government that it was targeting the university because it had allowed antisemitism to run rampant on its campus.

“The government-initiated onslaught against Harvard was much more about promoting a governmental orthodoxy in violation of the First Amendment than about anything else, including fighting antisemitism,” Burroughs wrote in an 84-page opinion.

Judges appointed by Republican presidents – including Trump – have also ruled against the president in high-stakes First Amendment disputes.

“In terms of their First Amendment record in the lower courts, it’s abysmal,” said Timothy Zick, a professor at William & Mary Law School who specializes in First Amendment law. “There are very few lower court wins for the administration.”

Some of the more notable examples, Zick said, have come in immigration detention cases, where judges have ordered officials to release individuals the government is seeking to deport because their political views are at odds with the current administration.

In one such case concerning Tufts University PhD student Rümeysa Öztürk, a judge said that officials had provided no evidence to support keeping her detained while she challenged her deportation. Her “continued detention potentially chills the speech of millions,” US District Judge William K. Sessions III said in May.

When Trump tried to punish the Associated Press earlier this year after the outlet announced it would not follow his lead in referring to the “Gulf of Mexico” as the “Gulf of America,” a judge appointed to the bench by Trump during his first term made clear that such government retaliation crossed the First Amendment’s red line.

Judge Trevor McFadden said that the AP had shown that the administration’s decision to limit its access to his events, the Oval Office and Air Force One represented impermissible government retaliation for the outlet’s “exercise of its First Amendment freedoms.”

“Under the First Amendment, if the Government opens its doors to some journalists – be it to the Oval Office, the East Room, or elsewhere – it cannot then shut those doors to other journalists because of their viewpoints,” he wrote. “The Constitution requires no less.”

But that ruling eventually led to one of the rare First Amendment court wins for the administration. A federal appeals court in Washington, DC, later allowed the limitations to largely stand as the case continues.

In a series of other cases brought by elite law firms against executive orders from Trump targeting them for employing his perceived political enemies or representing clients who have challenged his initiatives, judges held no punches as they chided him for the actions.

Judge Richard Leon, an appointee of former President George W. Bush who sits in DC, said in one of those cases that an order targeting the firm WilmerHale was an “egregious” violation of the First Amendment.

The order’s provisions – which included denying the firm’s attorneys access to federal buildings and suspending security clearances for the lawyers – Leon wrote, “constitute a staggering punishment for the firm’s protected speech!”

Three other judges issued similar rulings blocking orders aimed at other law firms, including District Judge Beryl Howell, who struck down an order targeting the firm Perkins Coie after deciding that it is “contrary to the Constitution, which requires that the government respond to dissenting or unpopular speech or ideas with ‘tolerance, not coercion.’”

All of the law firm cases have been appealed by the administration.

“They lost all the law firm cases. They’ve lost every international student bail case. And in both of those contexts, it’s interesting to note, the fundamental claim is that the Trump administration has retaliated against law firms, against international students,” said Zick. “Retaliation has become sort of a central theme in all those cases.”

In several other cases dealing with the administration’s attempt to go after federal employee unions or crack down on diversity, equity and inclusion initiatives, judges have written critically about the government’s approach to First Amendment protections.

Judge Adam Abelson in Baltimore, for example, ruled earlier this year that the administration could not enforce an executive order that sought to dismantle DEI programs through leveraging federal funding in a way that could unconstitutionally chill private speech.

The order’s provisions, he wrote, “are content- and viewpoint-based restrictions that chill speech as to anyone the government might conceivably choose to accuse of engaging in speech about ‘equity’ or ‘diversity’ or ‘DEI.’”

A federal appeals court has put that ruling from Abelson, an appointee of former President Joe Biden, on hold for now.

It’s possible that some of these cases may not reach final resolution for some time and the administration has signaled a willingness to take many of the cases holding up its agenda to the Supreme Court for review.

But some legal experts say the administration’s losses in court may not ultimately matter if the First Amendment attacks succeed in curtailing speech in some quarters without taking any direct action.

“The administration is not trying to win on the law. They’re trying to win on the ground, and they’re being very successful at that,” said Alex Abdo, the litigation director of the Knight First Amendment Institute.

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