Chicago-based law firm fights Trump executive orders

In the escalating court battle between the Justice Department and major law firms over President Donald Trump’s punitive executive orders, Chicago-based Jenner & Block is leading a counteroffensive on the front lines in a Washington federal court.

Jenner & Block, which was targeted by a March 25 executive order to restrict the 111-year-old law firm’s access to federal agencies, filed a motion Tuesday seeking a permanent injunction to prevent Trump’s order from being enforced. It joins Perkins Coie and WilmerHale in taking the fight to court, backed by support from hundreds of smaller law firms across the country, who say the rule of law is on the line.

“No lawyer can effectively represent his client when full-throated advocacy that is not aligned with the government’s agenda risks governmental reprisal,” Jenner & Block states in the motion for summary judgment.

The filing argues the executive order violates the First Amendment and unlawfully retaliates against Jenner & Block for “speech and association the government does not like.”

The motion follows a temporary restraining order granted last month by U.S. District Judge John Bates blocking key portions of Trump’s action against Jenner & Block that would have terminated federal contracts and limited the firm’s access to federal buildings, making it difficult to represent many clients.

“The Order singles out Jenner for sanction, adopting a comprehensive series of restrictions and attempting to use nearly every lever at the President’s disposal to limit Jenner’s effective advocacy for its clients,” the Jenner & Block motion states.

Trump’s executive order also singled out former Jenner & Block attorney Andrew Weissmann, a lead prosecutor in special counsel Robert Mueller’s two-year investigation into Russian interference in the 2016 presidential election.

Jenner & Block filed a lawsuit challenging the executive order on March 28, naming the Justice Department, federal agencies and cabinet heads on a long list of defendants. The firm’s April 8 motion for summary judgment and a permanent injunction reiterates its contention that the executive order exceeds the president’s constitutional authority and violates the separation of powers.

“These orders send a clear message to the legal profession: Cease certain representations adverse to the government and renounce the Administration’s critics — or suffer the consequences,” Jenner & Block’s motion states.

In response, the Justice Department filed a motion April 8 seeking to dismiss Jenner & Block’s lawsuit, citing among other things improperly naming the United States as a defendant as an “attempted end-run” to “dodge the well-settled prohibition against courts enjoining the President.”

A former federal prosecutor branded as “unethical” in Trump’s executive order, Weissmann was a partner at Jenner & Block from 2006 to 2011, and again from 2020 to 2021.

From 2002 to 2005, Weissmann helped lead the Justice Department’s Enron Task Force, supervising the prosecution of more than 30 people in connection with the Houston energy company’s collapse amid an accounting scandal, including CEO Jeffrey Skilling, the brother of retired WGN-TV weatherman Tom Skilling.

But it was his leading role in the Mueller investigation that earned Trump’s ire, making Weissmann “a frequent political target of the President,” according to the Jenner & Block lawsuit.

“Mr. Weissmann does not work at Jenner,” the firm states in its motion for summary judgment.

In its motion to dismiss, the Justice Department calls the efforts to distance the law firm from Weissmann “revisionist history,” despite issuing the executive order nearly four years after his departure from Jenner & Block.

“Jenner & Block publicly praised Weissmann’s role in the Mueller investigation, and backed up that praise by rehiring him,” the Justice Department’s motion states.

Founded in Chicago in 1914, Jenner & Block represents large corporations, universities, emerging companies and individuals, and prides itself on being a top pro bono firm. Chicago remains the largest office, but Jenner & Block has more than 500 lawyers across multiple markets including New York, Los Angeles, London, San Francisco and Washington.

Jenner & Block is one of several large law firms that have been targeted by Trump executive orders in the first few months of his second term.

On Feb. 25, Trump issued an executive order suspending security clearances for Covington & Burling, the Washington-based law firm that represented Jack Smith, the former special counsel who oversaw criminal investigations into the then-former president.

That was followed by a March 6 executive order suspending security clearances and restricting federal access for Perkins Coie, the Seattle-based law firm that represented Hillary Clinton during her 2016 presidential campaign. Perkins Coie filed an ongoing federal lawsuit March 11 challenging the executive order as unconstitutional.

On March 14, Trump targeted New York-based law firm Paul, Weiss, Rifkind, Wharton & Garrison for bringing a pro bono suit against January 6 participants and for rehiring Mark Pomerantz, an attorney who previously left the firm to join the Manhattan district attorney’s office “solely” to prosecute the president, according his executive order.

Paul Weiss struck a deal that “acknowledged the wrongdoing” of former partner Pomerantz and also agreed to provide $40 million of pro bono work to causes favored by Trump, who revoked the initial executive order March 21.

The firm faced backlash in the legal community for the decision to reach a settlement. On Tuesday, Trump suggested big law firms that cut a deal with the White House would be putting their pro bono commitments to work propping up the struggling coal industry.

Others have chosen to fight, including Washington-based WilmerHale, which filed a federal lawsuit and was granted a temporary restraining order March 28 – the day after a Trump executive order suspended the firm’s security clearances and restricted federal access for rehiring former partner and since-retired Mueller at the conclusion of his special counsel investigation.

WilmerHale also filed a motion for summary judgment Tuesday, calling the executive order sanctioning the law firm “a textbook example of retaliation for constitutionally protected expression” in violation of the First Amendment.

Perkins Coie, which was granted a temporary restraining order March 12 to block Trump’s executive order targeting the firm, also filed a motion for summary judgment last week.

On Monday, an amicus brief filed by 16 bar associations, including the Chicago Bar Association, and signed by 500 law firms, expressed support for Perkins Coie’s motion for a permanent injunction against Trump’s order, calling it “blatantly illegal” and an attempt to “intimidate lawyers into submission” to the executive branch.

About a dozen Chicago law firms signed the brief, including Clifford Law, Edelson and Jenner & Block, one of the few so-called Big Law firms on the list.

“This isn’t a political issue. This is a constitutional and legal issue regarding the rule of law,” John Sciaccotta, Chicago Bar Association president, said Wednesday. “I think it’s important for people to choose their lawyers, and I think it’s important for lawyers to choose their clients.”

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