Jed Rubenfeld: Donald Trump’s War on Big Law

Over the past month, the White House has issued five executive orders targeting big white-shoe law firms associated with prominent anti-Trump lawyers. It’s not surprising that Trump would do such a thing. What’s strange is that the language of his orders maximizes their own likely unconstitutionality.

The most recent order, issued on March 27, singles out the D.C.-based firm Wilmer Cutler Pickering Hale and Dorr, which employs more than 1,100 lawyers. It revokes security clearances held by WilmerHale attorneys; prohibits the federal government from hiring WilmerHale employees absent a special waiver; orders a review and the possible termination of federal contracts with entities that do business with the firm; calls for the withdrawal of government goods or services from the firm; and calls for restrictions on the ability of WilmerHale employees to enter federal buildings (presumably including federal courthouses) and on their “engaging” with government employees.

Trump issued similar orders against the Chicago-based Jenner & Block on March 25, the New York-based Paul, Weiss on March 14, the Seattle-based Perkins Coie on March 6, and the D.C.-based Covington & Burling on February 25.

Several of the orders accuse the targeted firms of unlawful discrimination through their DEI policies. The most recent says that WilmerHale "discriminates against its employees based on race and other categories prohibited by civil rights laws, including through the use of race-based ‘targets.’ ”

Had the orders stopped there, they would be on much more solid constitutional ground. Instead, they have—with increasing candor—explicitly targeted the firms for representing causes Trump opposes and associating with lawyers perceived to be adversaries of the president.

For example, the sins attributed to WilmerHale include engaging in “partisan representations to achieve political ends,” litigating in favor of affirmative action, and doing pro bono work for illegal aliens. WilmerHale is also condemned for hiring three named lawyers, including Robert Mueller, after they participated in what the order calls “one of the most partisan investigations in American history.”

Similarly, Jenner & Block’s apparent sins include taking on “partisan representations to achieve political ends,” advocating for illegal aliens, opposing “the biological reality of sex,” and being “thrilled” to rehire Andrew Weissmann (who is no longer with the firm), another leading Mueller investigation lawyer, whom Trump has in the past called “scum.”

Whatever you think of the Mueller investigation, law firms undoubtedly have a First Amendment right to take on “partisan representations to achieve political ends” and to hire as many anti-Trump lawyers as they like. Everyone is entitled to legal representation—that’s the very basis of the American legal system—and retaliating against law firms for their “partisan” lawyering or hiring political enemies is blatantly unconstitutional.

What’s strange is that these orders do not even try to hide their retaliatory purpose. Rather, they highlight it. This has led the two federal courts looking at these orders–in separate cases brought by Jenner and WilmerHale–to immediately issue temporary restraining orders, with one judge writing, “The retaliatory nature of the Executive Order at issue here is clear from its face.”

The question is why. Why would those drafting these orders maximize the odds of their being found unconstitutional?

First, because even if illegal, the orders can serve as leverage, forcing firms to bend the knee. Paul, Weiss quickly struck a deal with the White House to get the order against it rescinded. Another major white-shoe firm, Skadden, Arps, has reportedly made a similar deal preemptively. That’s not a proper use of presidential power, but it can be an effective one.

Second, because the potential legal consequences for Trump are low. Even if the orders are found to violate the First Amendment, current constitutional law entitles the firms only to an injunction, not damages.

But perhaps most important, Trump is unapologetically sending a message: What Big Law did to me, I’m going to do to them.

During the Biden years, Big Law wouldn’t touch Trump with a 10-foot pole. Some attribute this to Trump’s poor bill-paying reputation, but big-boy law firms are perfectly capable of getting paid in advance. No, the reasons were ideological, as well as self-interested. America’s biggest law firms lean decidedly liberal. A study of amicus briefs filed in the highest-salience Supreme Court cases found that 95% of the Big Law briefs supported the liberal position. Moreover, these firms feared being blackballed: they were afraid that if they represented Trump or Trump-associated causes, clients and young lawyers would go elsewhere.

During the Biden years, staying away from Trump was a very good way to cozy up to the administration. But it wasn’t just Trump they avoided: major American law firms parted ways with lawyers who dared to support conservative causes; Paul Clement, for example, was forced to leave Kirkland & Ellis because of his Second Amendment litigation.

Trump opponents will point out that when firms like Kirkland sever ties with lawyers like Paul Clement, that’s private-party conduct, not governmental persecution of conservative lawyers. True, but don’t forget pro-Trump lawyer Ken Chesebro not only lost his New York law license, but was criminally prosecuted for coming up with a long shot legal strategy to replace Biden-supporting electors after the 2020 election.

You can disagree all you want with Chesebro’s legal theory; you can hate his position on the 2020 election. But what was done to him was no less outrageous than what Trump is doing to Andrew Weissmann.

A similar dynamic is playing out in Trump’s efforts to deport Columbia University activist Mahmoud Khalil and alleged members of the Tren de Aragua gang. Here, critics have a strong argument that the Venezuelan deportations violate due process, and a non-crazy argument that the Khalil deportation violates freedom of speech. But again, Trump is sending a message: Don’t tell me about due process and the First Amendment, not after Democrats for years threw due process out the window, systematically suppressed speech online, and sought to bankrupt and lock up the leading Republican presidential candidate through unconstitutional prosecutions.

Of course, two wrongs do not make a right. But it’s important to see what things look like to supporters of the president. Imagine you’re playing in an NFL game and the other team keeps tackling your receivers when the ball is still in the air and the refs never call pass interference. What are you supposed to do when you’re on defense—abide by the rules when the other team doesn’t? If you do, you’re going to lose.

It’s hard to predict, but easy to overhype, the real-world consequences these law firms face as a result of these executive orders. That Paul, Weiss and Skadden, Arps cut deals indicates that the firms perceive a significant threat to their bottom lines, especially in the form of lost clients. On the other hand, Paul, Weiss didn’t actually have to give up much to get its order rescinded; reports of the magnitude of the firm’s concessions are greatly exaggerated. And the firms that fight these orders in court, like Perkins, Jenner & Block, and WilmerHale (represented by none other than Paul Clement), are very likely to win. Arguably, then, these executive orders are more about optics than consequences.

But the constitutional danger is real: a spiral into ever-increasing unconstitutionality, first by one administration, then the next. In short, it seems we’ve officially entered a new phase of the Trump era: the reaping-the-whirlwind phase. And the question is what will remain standing when that phase is done.

Unfortunately, this is a legal problem for which the legal system may offer no solution.