CHICAGO — A federal judge on Friday struck down an executive order signed by President Donald Trump earlier this year targeting the Chicago law firm Jenner & Block, ruling the effort ran afoul of the Constitution’s First Amendment.

The decision from US District Judge John Bates in Washington, DC, represents the second time in recent weeks a judge has thwarted Trump’s attempt to retaliate against a top law firm.

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“This order, like the others, seeks to chill legal representation the administration doesn’t like, thereby insulating the Executive Branch from the judicial check fundamental to the separation of powers,” Bates, an appointee of former President George W. Bush, wrote in the ruling. “It thus violates the Constitution and the Court will enjoin its operation in full.”

“The challenged executive order targets Jenner for what it has said and thereby attempts to dampen what it might yet say. That is unconstitutional under any view of the First Amendment,” the judge concluded.

The order from Trump targeting Jenner & Block instructed federal agencies to terminate contracts with the firm and its clients, limited the firm’s access to federal officials and buildings and suspended the security clearances for attorneys at the firm.

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Shortly after the law firm sued, Bates paused parts of the order while the case unfolded. But his new ruling goes significantly further by overturning every part of the order.

Earlier this month, another judge in Bates’ courthouse similarly overturned a separate order from the president that targeted the firm Perkins Coie. Several other cases brought by other firms facing a retaliatory executive order are still pending.

Jenner & Block is a large law firm with a Washington, DC, office that’s part of several prominent and politically charged cases, and it has several well-known courtroom lawyers, regulatory attorneys and Congress specialists in its partnership. The law firm previously employed former prosecutor Andrew Weissmann, who led the successful prosecution of Trump’s 2016 campaign leader Paul Manafort as one of the top prosecutors in the Russia investigation.

The Jenner & Block order, signed by Trump in March, claimed that the firm has “abandoned the profession’s highest ideals, condoned partisan ‘lawfare,’ and abused its pro bono practice to engage in activities that undermine justice and the interests of the United States.” The executive order specifically points out Weissmann’s ties to the firm.

At the time it was issued, the firm was involved in some of the emergency lawsuits challenging Trump’s executive actions, including cases concerning the administration’s effort to cutting medical research funding to universities and its attempt to curtail access to gender-affirming care for minors.

The lengthy ruling from Bates was particularly critical of how Trump’s order would negatively impact the firm’s ability to do pro bono work on behalf of clients it wants to take on.

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“When law firms volunteer to represent vulnerable individuals and groups without pay, they embody the best of the profession,” he wrote. “This order and the others like it seek not only to prevent that noble undertaking but to manipulate it. The orders strongarm firms into redirecting their uncompensated services to work the President prefers – or even perhaps to work for the President himself.”

He continued: “So when this order retaliates for (and endeavors to steer) Jenner’s ‘powerful pro bono practice,’ it sullies a tradition that instructs lawyers to pursue ideals higher than profit. The public will suffer.”

This story has been updated with additional details.

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