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Two law firms sued the US government on Friday over executive orders by Donald Trump, alleging that the actions targeting them undermined the rule of law.

Jenner & Block and WilmerHale filed lawsuits to block what they characterise as the unconstitutional directives, which penalise the firms for ties to a federal investigation into alleged Russian interference in the 2016 presidential election.

Their moves came as Trump hailed what he said was a $100mn settlement with a third law firm, Skadden Arps, which had sought to head off a similar order.

The executive orders against Jenner & Block and WilmerHale call for the review or termination of government contracts with not only the law firms but also entities doing business with them, as well as asking federal agencies to suspend security clearances for the firms’ staff.

WilmerHale said on Friday that the move constituted “a plainly unlawful attack on the bedrock principles of our nation’s legal system — our clients’ right to counsel and the First Amendment”, which protects freedom of speech. 

Jenner & Block attacked the executive order against it as “an unconstitutional abuse of power against lawyers, their clients, and the legal system . . . intended to coerce law firms and lawyers into renouncing the Administration’s critics”.

The lawsuits, which note that a federal judge has already blocked a similar order against Perkins Coie, escalate a fight between the White House and the country’s top law firms.

“The Trump administration is working efficiently to eliminate waste, fraud and abuse in the federal government,” Harrison Fields, White House deputy press secretary, said in response to Jenner & Block’s lawsuit. “It is absurd that a multimillion-dollar law firm is suing to retain its access to government perks and handouts.”

Referring to the challenge by WilmerHale, Fields said Trump’s executive orders were “lawful directives to ensure that the president’s agenda is implemented and that law firms comply with the law”, contrasting them with what he characterised as the weaponisation of the legal process by Democrats.

WilmerHale is being represented by Paul Clement, who was solicitor-general under former president George W Bush and is known for defending conservative causes.

He said on Friday that the firm’s lawsuit was “absolutely critical to vindicating the First Amendment, our adversarial system of justice, and the rule of law”.

Trump has taken aim at his perceived opponents in Big Law, targeting firms with historical affiliations to the Democratic party or former prosecutors who have probed the president.

Similar orders have been targeted at Paul Weiss as well as Perkins Coie. Another order directed at Covington & Burling was narrower in scope. 

But a division is now emerging between the top US law firms that have chosen to fight and those that have capitulated to Trump’s demands.

Paul Weiss, a larger firm, struck a deal directly with the president to quash an order it said would have hindered its business.

It pledged measures including $40mn of pro bono legal services for causes the administration supports, such as fighting antisemitism and supporting veterans.

Skadden Arps, which Trump ally Elon Musk attacked last week for taking a pro bono case against rightwing provocateur Dinesh D’Souza, did not immediately respond to a request for comment on Friday.

But the US president said the law firm had “essentially” reached a settlement in which it would provide $100mn in pro bono work of which the administration approves.

Both the executive orders and the Paul Weiss deal have sent shockwaves through the legal industry, as law firms race to draw up contingency plans in case they are targeted by the White House. 

The order targeting Jenner & Block said Andrew Weissmann, a former partner at the firm who worked on the probe looking into alleged collusion between Russia and Trump’s victorious 2016 campaign, engaged in “partisan prosecution as part of Robert Mueller’s entirely unjustified investigation”.

Then-special counsel Mueller, who headed the probe, found no evidence of collusion. Weissmann, now a professor at NYU law school, has not responded to a request for comment on the order. Trump’s order against WilmerHale cited Mueller’s relationship with the firm, from which he retired in 2021.

The directive against Jenner & Block also said it “abused its pro bono practice to engage in activities that undermine justice and the interests of the United States”, citing what appeared to be cases challenging the administration’s positions on immigration and transgender issues.  

In response, the law firm said that deciding not to fight the directive “would mean compromising our ability to zealously advocate for all of our clients and capitulating to unconstitutional government coercion, which is simply not in our DNA”.