A federal appeals court on Thursday appeared skeptical of the constitutionality of the Trump administration’s efforts to punish major law firms, showing little appetite to depart from findings by lower-court judges last year that penalties targeting the firms were unlawful.
Months after taking office, Mr. Trump signed a series of executive orders imposing penalties against major law firms that had previously employed or done legal work for president’s political opposition. The orders canceled their federal contracts, revoked lawyers’ security clearances and barred the firms’ staff from entering federal buildings.
A few firms cut deals with the administration, agreeing to do free legal work toward the president’s goals, in exchange for relief from the penalties. But several firms, including Perkins Coie, WilmerHale, Susman Godfrey and Jenner & Block balked and sued.
The hearing in front of three federal appeals judges highlighted the lengths to which the Trump administration has gone to extract concessions from the firms. It came after the Justice Department first told the appeals court that it would abandon efforts to appeal, as the president pivoted his attention to other partisan vendettas and political prosecutions, before reversing course.
At the hearing, the four firms, as well as Mark Zaid, a lawyer who had represented a whistle-blower in connection with Mr. Trump’s first impeachment, each revisited their claims that the administration’s actions had violated their constitutional rights.
“These executive orders run afoul of the better part of the Bill of Rights,” Paul D. Clement, a veteran appellate lawyer and former solicitor general under President George W. Bush, representing the firms told the judges.
Mr. Clement said the orders were designed to upend the legal profession and were littered with “constitutional defects,” infringing on free speech protections, the right to counsel, and equal protection under the law.
The three judges spent significant time on one of the penalties contained in the orders: the attempt to withdraw security clearances from disfavored lawyers. The judges explored whether the courts can question a president’s reasons for extending or withdrawing clearances.
Abhishek Kambli, a deputy associate attorney general arguing on behalf of the administration, compared the power to extend security clearances to the president’s power to pardon: a complex calculus of executive power that judges cannot ultimately scrutinize. He said lower-court judges overstepped by blocking the orders.
“The district courts here rushed to judgment on executive orders that they clearly didn’t like the content of, and in the process, granted relief that they were not authorized to do,” he said.
Chief Judge Sri Srinivasan and Judge Cornelia Pillard, both Obama appointees, asked pointed questions about how far a president could go in denying clearances before a court could step in.
Judge Pillard pressed Mr. Kambli to explain whether a president could, for instance, deny security clearances only to firms representing ethnic minorities or religious groups without triggering a review.
“How can you maintain that the executive orders are concerned with handling of classified information when the president rescinded his order against the Paul Weiss law firm, when the firm aligned itself with his political priorities and offered pro bono services?” she asked, referring to one of the firms that reached a deal with the administration.
The nine firms that acquiesced to the administration’s demands collectively pledged nearly $1 billion of pro bono work, with some being assigned to tasks related to Mr. Trump’s trade deals at the direction of Boris Epshteyn, one of Mr. Trump’s personal lawyers.
There was near unanimity in the lower courts that other forms of penalties included in the orders were likely unlawful, and the appeals court spent little time discussing them.
Judge Beryl A. Howell, who handled Perkins Coie’s case, had cited Shakespeare’s Henry VI to describe the orders as coercion. Judge Richard J. Leon, who considered WilmerHale’s case, wrote that anything short of striking down the order “in its entirety” would be “unfaithful to the judgment and vision of the founding fathers.”
Of the three judges who heard the case on Thursday, Judge Neomi Rao, a Trump appointee, appeared sympathetic to some of the administration’s arguments, questioning whether the courts could order security clearances reinstated after they were revoked. She said she worried about lower courts micromanaging the clearance process, checking individual determinations.
Mr. Clement told the panel it should not try to dissect the executive orders to find lawful parts it could salvage. He said the orders in their totality were designed to intimidate all law firms, and urged the court to strike them down entirely.
“This was shouted from the rooftops,” he said. “And part of the point of shouting it from the rooftops was to get the Paul Weisses of the world, the Kirkland Ellises of the world, the Latham and Watkinses of the world, to come and make deals with the government and volunteer close to a billion dollars in free legal services.”
Zach Montague is a Times reporter covering the federal courts, including the legal disputes over the Trump administration’s agenda.
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