WASHINGTON – Another federal judge in Washington has expressed skepticism on the legality of President Donald Trump’s executive order targeting a prominent law firm, saying he was concerned that the clear purpose of the edict was punishment.

U.S. District Judge John Bates had already temporarily halted the Trump administration’s executive order against the firm of Jenner & Block but heard arguments Monday on a request by the firm to block it permanently. Lawyers for two other firms — Perkins Coie and WilmerHale — made similar arguments last week to judges who appeared receptive to their positions.

Like the other judges, Bates did not immediately rule but repeatedly pushed back against a Justice Department’s claims that the orders against Jenner and other law firms were not meant to punish them. The executive orders have generally imposed the same sanctions against the law firms, including ordering that security clearances of attorneys be suspended, that federal contracts be terminated and that lawyers be barred from accessing federal buildings.

“It’s trying to punish Jenner by stopping the flow of money to Jenner,” Bates said. He later asked: “Isn’t it logical that clients are going to be reluctant to engage Jenner & Block if they know there’s a real chance that Jenner and Block isn’t going to be able to go into a federal building or talk to federal agencies?”

Justice Department lawyer Richard Lawson said it was premature to make that assessment because guidelines governing how the executive order is to be implemented had not yet come out.

Michael Attanasio, a lawyer who presented arguments on behalf of Jenner & Block, said it was “surreal” to listen to the Justice Department’s “verbal gymnastics” in rationalizing the order and said

“This order is designed to do one thing: it’s designed to punish a law firm because of the cases it take and because of its affiliation with a critic of the president,” Attanasio said. That’s a reference to the fact that the executive order against the firm takes note of the fact that it previously employed Andrew Weissmann, a prosecutor on special counsel Robert Mueller’s team that investigated Trump during his first term.

“All we need to do is read this thing,” Attanasio said. “It reeks of unconstitutionality. It should be set aside in its entirety.”

Each of the law firms subject to an executive order that has challenged it in court has succeeded in getting it temporarily blocked. Other firms, by contrast, have opted to preemptively reach agreements with the White House to avoid getting targeted.