The other shoe drops: Deals with Trump are already backfiring on top law firms

The Big Law firms that capitulated to President Donald Trump’s unconstitutional demands thought they were buying peace with his administration, preserving their client relationships, and protecting their bottom lines.

Recent developments illustrate the growing magnitude of their mistake.

Fighters Are Winning

On May 2, U.S. District Court Judge Beryl Howell became the first court to issue a final ruling that Trump’s executive orders targeting Big Law firms violated the First, Fifth, and Sixth Amendments to the U.S. Constitution. In a 102-page opinion, the court shredded Trump’s edict with a straightforward analysis that other courts are likely to follow:

“In a cringe-worthy twist on the theatrical phrase ‘Let’s kill all the lawyers,’ [Trump’s Executive Order] takes the approach of “Let’s kill the lawyers I don’t like,” sending the clear message: lawyers must stick to the party line, or else.

“Using the powers of the federal government to target lawyers for their representation of clients and avowed progressive employment policies in an overt attempt to suppress and punish certain viewpoints, however, is contrary to the Constitution,…. Simply put, government officials ‘cannot . . . use the power of the State to punish or suppress disfavored expression.’

“That, however, is exactly what is happening here.”

For those keeping score, Trump’s Justice Department has now lost every courtroom fight on the subject. Jenner & Block, WilmerHale, and Susman Godfrey obtained immediate temporary relief from his executive orders, as did Perkins Coie, which has now won a permanent injunction from Judge Howell.

Meanwhile, how are the firms that caved to Trump doing?

The Other Shoe Drops: #1

After providing Trump with a war chest totaling almost $1 billion in free legal services, the settling firms are now learning how he plans to use it. Previously, Trump had mused about using Big Law attorneys on coal leasing and tariff deals, but on April 28 things got real.

Trump issued an executive order titled, “STRENGTHENING AND UNLEASHING AMERICA’S LAW ENFORCEMENT TO PURSUE CRIMINALS AND PROTECT INNOCENT CITIZENS.”

The order emphasized the need to “protect and defend law enforcement officers wrongly accused and abused by State or local officials.” It directed Attorney General Pam Bondi to provide the legal resources necessary to defend those officers, including “private-sector pro bono assistance.” [emphasis supplied]

Stated simply, police officers accused of brutality and other misconduct will get Big Law attorneys to defend them – free of charge.

Meanwhile, traditional pro bono causes, including defending immigrants’ rights, are suffering from the deterrent effect of Trump’s attack. Fearing his wrath, they are declining work that challenges his policies.

Settling firms were already getting blowback from their partners and associates as many have left their firms. Trump’s newly-added page to their pro bono catalog won’t help recruiting or retention. And as with all things Trump, there’s no limiting principle. Appeasement never produces finality.

The Other Shoe Drops: #2

The firms’ stated reason for capitulating to Trump was concern that clients would leave any firm that was not in Trump’s good graces. That premise is not aging well either.

On April 11, Simpson, Thacher & Bartlett agreed to provide $125 million in pro bono work “and other free legal services” to Trump-designated causes.

On April 22, the firm informed the Delaware Chancery Court that it would no longer be representing Microsoft in a case related to its 2023 acquisition of Activision. The same day, Jenner & Block replaced Simpson Thacher as Microsoft’s counsel.

Losing a client to another firm is not uncommon, and none of the players has commented on Microsoft’s switch. But capitulation to Trump has not been a panacea for preserving client relationships. A firm that challenges an unconstitutional order threatening its existence is a firm that many clients want fighting for them.

The Other Shoe Drops: #3

On April 24, 16 House members sent letters to nine firms that settled with Trump. Asking about their motivations and urging them to disavow the deals, lawmakers suggested that the agreements may violate federal and state criminal and civil laws while creating “potentially irresolvable violations of applicable Rules of Professional Conduct.” Previously, Sen. Richard Blumenthal (D-Conn.) and Rep. Jamie Raskin (D-Md.) sent requests for information from several firms and White House counsel on April 6 and April 18.

The Other Show Drops: #4

Firms assumed that capitulation would occupy a single news cycle and then disappear. But their public relations nightmares aren’t going away. Apart from the widespread and ongoing condemnation of the legal community, the story continues to have legs as a fateful moment for the rule of law in the United States.

The May 4 edition of CBS’s 60 Minutes ran a damning segment on Big Law firms that settled with Trump. None was willing to appear and defend itself or its deal. The legal term for such continuing cowardice is res ipsa loquitur – the thing speaks for itself. In this case, the firms didn’t speak at all.

On May 9, an article that later appeared in the New York Times Sunday print edition ran with this headline and subhead:

Can Elite Lawyers Be Persuaded to ‘Wake Up and Stand Up’?

When the law firm Paul Weiss cut a deal with the Trump administration, a new kind of activist emerged.

Some of the settling firms, including Kirkland & Ellis and at least one other, have an escape hatch: Their “handshake deals” with Trump are not in writing. They can do what Trump does when he no longer likes his own prior agreement: Walk away.

In fact, even firms with a written agreement can walk away too. Whatever their form, the deals are probably not enforceable. But that was never Trump’s main objective. It was always about intimidation and deterrence. When firms bent the knee to him, he won and scored an invaluable public relations victory.

And his accompanying billion-dollar windfall didn’t hurt.

NOW READ: The single stupidest statement about Trump ever made