President Donald Trump is going after a pair of major law firms — and attacking the First Amendment in the process.
Trump issued an executive order on Thursday that took aim at Perkins Coie, a law firm that represented Hillary Clinton when she ran against Trump in 2016. Notably, Perkins Coie hired a research firm that produced the infamous “Steele dossier,” which alleged the president colluded with Russia to steal the election. Trump’s order aims to strip the firm’s attorneys of their security clearances and asks the government to review all contracts with the firm with the intention of terminating any they can.
Trump issued a similar memorandum last month, going after some attorneys at the law firm of Covington & Burling. The firm is home to former special counsel Jack Smith, who led the prosecution of Trump in cases related to the January 6, 2021, insurrection at the US Capitol and the president’s alleged mishandling of classified documents. (Both cases were dismissed after Trump won the 2024 election.) The memorandum aims to strip security clearances from Peter Koski, a partner at the firm based in Washington, DC, and any other individuals who helped Smith while he served as special counsel.
Canceled contracts promise to cost the firms revenue while stripping security clearances hurts them by putting certain areas of federal business off-limits. But the issue is far bigger than harm to a pair of well-off law firms.
Legal experts say that Trump’s executive actions challenge the First Amendment right to free expression — and aim to send a signal to would-be opponents from well beyond just the legal profession. (The White House did not respond to a request for comment.)
“No one is going to cry for a big law firm,” said Katie Fallow, deputy director of the Knight First Amendment Institute at Columbia University. “But the idea of the government punishing a private entity based on the political positions it’s taken, or the speech it’s engaged in, or who it’s associated with, is terrible from a free speech and association standpoint.”
What the executive orders say
Thursday’s executive order accuses Perkins Coie of trying to “judicially overturn popular, necessary, and democratically enacted election laws, including those requiring voter identification,” as well as discriminating against applicants and staff by promoting diversity, equity, and inclusion policies. In addition to demanding that firm attorneys be stripped of their security clearances on that basis, it also orders government contractors to end their business relationships with the firm to the extent permitted by law and blocks the government from hiring firm employees.
The earlier memorandum concerning Covington & Burling similarly accused anyone at the firm who assisted Smith of “weaponization of the judicial process,” ordering the termination of their security clearances and government contracts with the firm.
Trump’s executive actions are not normal: Under President George W. Bush, a senior Pentagon official encouraged clients to cut their ties with law firms representing prisoners held at Guantánamo Bay, Cuba. But a month after his remarks, the official resigned and publicly apologized, asserting that he believed “that a foundational principle of our legal system is that the system works best when both sides are represented by competent legal counsel.”
Legal experts were not aware, however, of any incident in which a sitting president had done something similar via executive action.
Even for Trump, who has already sought retribution against his perceived enemies in the media and in the federal government, “this is just jaw-dropping,” said Laurence Tribe, a constitutional scholar at Harvard Law School. “This represents sort of a great escalation of a trend that was already evident.”
Why Trump’s targeting of law firms raise key constitutional concerns
Legal scholars say that Trump’s targeting of law firms likely violates the First Amendment and other constitutional protections.
The executive order seems to be taking aim at specific positions that Perkins Coie has taken on behalf of its clients, its views about employee management policies (including DEI programs), and its association with Democrats.
That language “absolutely suggests viewpoint discrimination,” which is prohibited by the First Amendment, said Catherine Ross, a professor at George Washington University Law School. Fallows and Tribe said they agreed.
Beyond that, Tribe also raised a concern that the executive order could violate the Sixth Amendment right to the effective assistance of counsel. That right, he said, is “gravely endangered if the executive branch can brand and ostracize a particular group of lawyers and strip them of the security clearances, without which they could not represent a number of the people that the administration either has gone after or has indicated an intention to go after.”
It’s not entirely clear, however, that the orders will be struck down in court, the analysts say.
Judges have historically deferred to the president on matters of national security, and that might provide some legal cover to Trump if the issue reaches the Supreme Court, Tribe said. But Ross also pointed out that Thursday’s executive order lacks specific details on any potential national security concerns. Instead, she said, it “appears to be aimed at preventing the firm from acquiring or maintaining clients.”
Trump’s attacks on the First Amendment should worry Trump’s perceived political opponents no matter what field they are in.
“This is the way dictatorships get going,” Tribe said. “People get afraid to say their piece — if they are lawyers, to represent a client who might be in the crosshairs of those in power. When that kind of fear casts a chill across the land, the ability of ordinary people to live their lives as they see fit gets undermined.”
