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Simpson Thacher and Jenner & Block—Big Law’s Answer to Goofus and Gallant—Show the Cost of Cowardice and the Economic Value of Courage

One Swallow Does Not a Summer Make—But I Think This is the Start of a Trend

N.Y. Times, Microsoft Drops Law Firm That Made a Deal With Trump From a Case

The Times writes,

When big law firms attacked by President Trump decided to make a deal with him rather than fight, many did so because their leaders feared that clients would abandon a firm caught on the administration’s bad side.

Now that logic may be getting less compelling. A major company, Microsoft, has dropped a law firm that settled with the administration in favor of one that is fighting it. … 

On April 22, several attorneys at the law firm Simpson Thacher & Bartlett informed the Delaware Court of Chancery that they would no longer be representing Microsoft in a case related to the company’s 2023 acquisition of the video game giant Activision Blizzard, according to court filings.

Simpson Thacher reached a deal with the White House last month in which the firm committed to perform $125 million in free legal work for causes acceptable to the Trump administration. In a joint statement with other firms making similar agreements, Simpson Thacher said the pro bono work would be on behalf of “a wide range of underserved populations.”

On the same day that the Simpson Thacher lawyers filed paperwork withdrawing from the Microsoft case, at least three partners at the firm Jenner & Block informed the court that they would be representing Microsoft in the case. Jenner is fighting in court to permanently block a Trump administration executive order targeting its business. …

In some cases, a client may worry that a law firm that has reached a deal with the White House has a conflict of interest that prevents it from aggressively representing the client. For example, the client may be a defendant in a lawsuit brought by the federal government and worry that a settling law firm would be reluctant to stand up to the administration.

Other clients may have broader concerns. A senior partner at another firm that does not have an agreement with the White House said his firm was beginning to attract clients from firms that had settled with the administration. The partner, who was not authorized to discuss client matters publicly, said prospective clients had indicated that they had lost confidence in settling firms for not standing up to an attack on the rule of law.

Some firms challenging the administration have sought to capitalize on this frustration, suggesting that their pushback reflects a commitment to fight on behalf of their clients as well.

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The First 100 Days, the Next 100 Days

Thomas B. Edsall (N.Y. Times), How Does a Stymied Autocrat Deal With Defeat?

Mr. Edsall writes,

The window of opportunity that allowed President Trump to overwhelm his adversaries with an onslaught of executive orders dismantling core American institutions is closing.

Public opinion has turned against him, the economy is faltering, the Supreme Court has ordered him to stand down, his tariffs have backfired, and such conservative mainstays as National Reviewand The Wall Street Journal are questioning his judgment.

How does a stymied autocrat deal with defeat? As the opposition gains strength, frustrating the nation’s commander in chief, how will Trump respond?

It is unthinkable to imagine him graciously acknowledging defeat, changing direction and moving on.

Will he claim victory in defeat? Will he try to provoke his adversaries into violence in order to invoke the Insurrection Act?

Trump’s unpredictability makes it impossible to answer these questions with any certainty, but as his actions in the first three months of his second term demonstrate, Trump’s choices veer to the extreme. …

If, in the face of adversity, Trump and his allies attempt to overturn democracy, what are their chances? I asked Herbert Kitschelt, a professor of international relations at Duke and the 2025 recipient of the prestigious Johan Skytte Prize in political science, that question, and he provided a nuanced reply by email: “No scientific, evidence-based investigation can currently provide a factually grounded prognosis” on “whether and how Trump and the Christian evangelical-nationalist-Southern wing of the Republican Party might break the democratic Constitution of the United States,” he wrote.

Instead, Kitschelt argued, it is possible to “outline the forces that may impinge on whether this process will take place or not.”

Kitschelt then specified the four factors working in favor of the establishment of “an authoritarian coalition in the United States”:

U.S. technological innovativeness and productivity gains — more so than in other advanced capitalist countries — have generated anxiety among many occupational groups.

The U.S. has a weak welfare state — in terms of pensions, health care, unemployment insurance, aid to families with children, public education — when compared to just about any other advanced capitalist country.

America is the most inegalitarian advanced Western country, in terms of income and wealth. That induces rich people to promote politicians who distract the economically worse off from questions of economic distribution and focus their attention on issues of political governance, culture war, racial and ethnic hierarchies and nationalist claims to global supremacy.

Unlike any other Western democracy, America has a deeply antidemocratic, intolerant, illiberal religious strand.

Kitschelt went on to describe conditions in the United States that “are adverse to the victory of an authoritarian coalition” and are, in contrast, favorable to democracy:

America’s civil society: If it awakens from its current shock and slumber, signs of which are already emerging, it is likely that it will become a powerful force to uphold democracy.

Most importantly: American capitalism, large segments of the U.S. business class, whether in finance, I.T. and A.I., U.S. manufacturers in global production chains (vehicles, aerospace, pharma, etc.) and U.S. culture industries are averse to a MAGA & Tea Party authoritarian coalition. Populism undercuts property rights and the rule of law, rendering it impossible to make rational, profit-generating, long-term business investments.

A severe economic crisis, which Kitschelt believes is probable, given current trends, would sharply undermine Republican prospects in the 2026 congressional elections, which might prompt Trump and his allies to “realize that they cannot win a free and fair election and actually might face a defeat in the midterms severe enough to precipitate the impeachment of both president and vice president.”

The question then becomes, in Kitschelt’s view:

Will evangelical-nationalist clero-fascism — with other MAGA and Tea Party currents in tow — be capable of converting America into an electoral autocracy faster than U.S. civil society and large parts of the business sector will be able to mobilize a defense of American democracy and to stiffen the spine of the U.S. judiciary to preserve American institutions?

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Judge Dugan’s Arrest, Civil Disobedience, the Authoritarian Playbook, Cosplay Fascism, and the Utility of Analytical Thinking

Please read these remarks in light of my comments, right below, on the character of judges.

By now, we have all read a lot about the authoritarian playbook. If, by and large, judges can’t be intimidated, can’t be bought, and can’t be fooled, then, presumably, the next step in the authoritarian playbook would be to start arresting them. 

We are now conditioned to look for that sort of thing to start happening. We hear that, a couple of days ago, the FBI arrested a state judge out in Milwaukee for something having to do with immigration. Our confirmation bias kicks in, and the chorus all proclaim in unison, “Well, the fascism is now beginning in earnest!”

To add to the circus atmosphere, Attorney General Blondi goes out in public to do her cosplay fascist act—encouraging us to fear that federal judges who follow the constitution and demand due process might risk arrest, too. See Aaron Blake (Washington Post), Pam Bondi’s striking comments on arresting judges.

As a side observation: most humans, myself included, try to make ourselves look morally better than we really are. But that seems to be going out of fashion. Now the Attorney General of the United States wants everyone to think she is Ilsa, the She Wolf of the SS. 

A sign of the times, I suppose.

We now return to our regularly scheduled program. 

Back in Milwaukee, Judge Dugan, learning that ICE was about to snatch one Eduardo Flores-Ruiz—a misdemeanor criminal defendant in a case before her— allegedly showed Señor Flores-Ruiz how to get out the side door, thereby delaying his capture by ICE by a few minutes.

I don’t know how many people witnessed this incident. I don’t know whether they all remember it the same way. I don’t know what Judge Dugan’s account is; I don’t know what she says she did or didn’t do, and I don’t know what she says about her her intent. Accordingly, I have no rational basis to reach a conclusion as to what actually went down.

I don’t know—because I haven’t researched the matter, and I don’t intend to do so—what are the words of the statutes that Judge Dugan is supposed to have violated. Nor do I know how these words have been interpreted in judicial decisions (“case law,” as we call it). I don’t know whether Judge Dugan’s conduct clearly violated the law, clearly did not violate the law, or fell into an ambiguous gray area. I don’t know whether she will claim to have consciously run a legal risk to herself in order to advance a higher moral principle. If she does make such a claim, I don’t how whether the evidence will back up her claim.

But here is something I do know. I do know that it would be unwise for our side to be tricked into arguing that “lawless behavior by our guys is OK, while lawless behavior by your guys is not OK.” 

Instead, we should just reserve judgment on the facts and the law in this case, agree that everybody who breaks the law should be punished—and that, sometimes, people who decide to break the law to promote righteousness should suffer legal punishment. And then we should erect a statue in their honor. 

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Two Things About Judges

Judges, as a group, share many, many things in common with the rest of the human race, as a group. But I want to mention two things that tend to set the judges apart. Two things that explain why the federal judiciary is holding it together, while, for example, the Skadden Arps Management Committee acts like a bunch of wusses. 

First of all, think for a moment about what judges actually do every day. Well, a lot of what they do is ensure that criminals get their just deserts. Many criminals are violent. Many criminals, just like Mango Mussolini, threaten retribution. Threats to federal judges have reached an alarming level.

If you are the kind of person who backs down whenever an asshole leaves a threatening voicemail, then, most likely, you are not a federal judge.

Secondly, if you are a federal judge, at any level, then the chances are very good that you could make a lot more money doing something else. They want to live comfortably, but, unlike the Skadden Arps Management Committee, their nights are not occupied with dreams of avarice.

Federal district judges make about $240 thousand a year; appellate judges, about $262 thousand; and associate justices of the Supreme Court, about $304 thousand. 

If you are a federal district judge, your compensation is the same as a second-year lawyer at one of the 100 top law firms. 

If you are a judge on one of the federal courts of appeals, then you are making a small fraction of the compensation of a partner at one of the top 100 law firms. 

The Chief Justice of the Supreme Court brings in a whopping $317 thousand. Back in the day, Chief Justice Roberts was a top partner of Hogan & Hartson, now Hogan Lovells, where the current profit per partner is more than $3 million a year. 

Hold that thought, while you remember George Conway’s offhand remark that the Paul, Weiss Management Committee chose to knuckle under to Trump because they were afraid their annual compensation would drop from $25 million to a mere $15 million. 

That’s why, facing off against the very richest of our top law firms, Trump could huff and he could puff and he could blow their house down. They were, metaphorically, the kind of little pig who builds his house out of straw or wood. 

Federal judges, as a group, are not that kind of little pig. They have physical courage. A lot of them have moral courage. And, for the most part, they can’t be bought. 

Nor, may I add, are they stupid. 

Trump gaslights.

But people try to gaslight every federal judge each and every day. Several times a day. They are used to it. It doesn’t work.