WASHINGTON – A federal judge on Friday permanently blocked another of President Donald Trump’s executive orders targeting a major law firm, calling it unconstitutional retaliation designed to punish lawyers for their legal work that the White House does not like.

The ruling from U.S. District Judge John Bates marks the second time this month that a judge has struck down a Trump executive order against a prominent firm. The decision in favor of Jenner & Block follows a similar opinion that blocked the enforcement of a decree against a different firm, Perkins Coie.

“Like the others in the series, this order — which takes aim at the global law firm Jenner & Block — makes no bones about why it chose its target: it picked Jenner because of the causes Jenner champions, the clients Jenner represents, and a lawyer Jenner once employed,” Bates wrote.

The spate of executive orders announced by Trump sought to impose the same consequences against the targeted firms, including suspending security clearances of attorneys and barring employees from federal buildings. The orders have been part of a broader effort by the president to reshape American civil society by targeting perceived adversaries in hopes of extracting concessions from them and bending them to his will.

Several of the firms singled out for sanctions have either done legal work that Trump has opposed, or currently have or previously had associations with prosecutors who at one point investigated the president.

In the case of Jenner & Block, the firm previously employed Andrew Weissmann, who served as a prosecutor on special counsel Robert Mueller’s team that investigated ties between Trump’s 2016 campaign and Russia.

Bates had previously halted enforcement of multiple provisions of the executive order against Jenner & Block and appeared deeply skeptical of its legality during a hearing last month.

In his ruling Friday, he said he was troubled that the orders retaliated against the firms for the “views embodied in their legal work” and seek “to chill legal representation the administration doesn’t like, thereby insulating the Executive Branch from the judicial check fundamental to the separation of powers.”

Two other firms, WilmerHale and Susman Godfrey, have also asked judges to permanently halt orders against them.

Other major firms have sought to avert orders by preemptively reaching settlements that require them, among other things, to collectively dedicate hundreds of millions of dollars in free legal services in support of causes the Trump administration says it supports.