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When I Left Big Law, I Learned This

May 27, 2026
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When I Left Big Law, I Learned This

One of the oddest things about becoming a lawyer — and one of the main reasons that I stopped working as one — is that you stop believing in fact and start believing in fiction.

I remember this acutely from my time working in Big Law. One of the first things you learn as a newly minted litigator is the basic structure of a legal brief. A brief is typically separated into two primary sections. First, the statement of fact, a plain recitation of the facts underlying the case; second, the argument, all your editorializing on top of that. In other words, you tell people what happened, and then you tell them your interpretation of it.

There is an intuitive logic to stating the facts before the interpretation: Something happens in the world; rational people present contrasting interpretations; the best interpretation wins.

It is also, of course, a fiction.

There is no such thing as a plain presentation of the facts. Every recounting of events comes with an interpretation. The interpretation happens when you decide what facts to include or omit; it happens when you decide the order in which the facts should be told; it happens when you decide what words will be used to describe them.

I’m doing it here. I told you I worked at a Big Law firm (fact) because I thought it would prompt a stronger reaction than telling you I worked at WilmerHale (also fact). I told you that the structure of a brief is one of the first things you learn (fact) because it seemed more dramatic than telling you about all the less interesting things you learn first (also fact). I told you that briefs consist of two primary sections (fact) because it was simpler than telling you that there are three or four more primary sections, too (also fact). And I chose this particular version of the facts because it was helpful to the point I am trying to make:

Our legal system is broken and in dire need of repair.

My view of this is colored by my own experience. I came to being a lawyer relatively late — at the ripe old age of 30 — and upon arriving at law school, immediately found myself immersed in a world that was both all-encompassing and totally bewildering in its blind faith and love for the law. The students beamed with excitement; the administrators constantly told us how important we were; the professors seemed to believe wholeheartedly in the efficacy of the judicial process. It was like signing up for an education and winding up in a cult.

But it is hard to live for more than a few months inside any environment without becoming a part of it. And so I fell in love with the law, too: with its beautiful intricacy, with the way it served as the meeting point between lofty philosophical ideals and real-world problems, with its storytelling power, which refined narrative and argument to a ruthless effectiveness. But I never lost that initial skepticism — particularly when it was my turn to enter the fabled echelons of a Big Law firm.

Big Law is the term used to describe the 100 or so largest firms in the United States and the huge ecosystem of money, jobs and power that orbits around them. It is a force that I found myself pushed toward both because of its early recruiting schedule, which happens far in advance of most other employers, and because it seemed like the logical place to begin a meaningful career while also having some measure of financial security.

Virtually every lawyer in the United States accepts the centrality of Big Law in our society. For instance, big firms litigate the vast majority of Supreme Court cases, and former Big Law lawyers overwhelmingly populate the ranks of federal judges, the offices of the administrative state and corporate leadership.

So when I arrived at WilmerHale fresh out of law school, there was the sense of having reached the meritocratic pinnacle of the profession: a group of brilliant intellectuals all working to help one another better serve our country’s legal system. The people I worked with were rigorously ethical, and by and large believed fiercely in the same liberal ideals that I did. Collectively, we worked on many cases that sought to make the world better, often pro bono, and occasionally we even succeeded: Helping to secure reproductive rights in Ohio after the 2022 ruling in Dobbs v. Jackson Women’s Health Organization and prohibit the disenfranchisement of hundreds of thousands of Virginians were meaningful victories.

On the other hand, there was the day-to-day reality: using our very expensive knowledge to manipulate the legal system in service of making the rich even richer. Because no matter the intent or how many pro bono cases it handles, what a Big Law firm spends the overwhelming majority of its time doing is fighting to create legal precedent that will entrench the power of those who already have it.

If these two things seem incompatible, it’s because they are. The fact that WilmerHale was a wonderful place to work was part of the problem. In Big Law, there is a sense that the immense power and wealth of your firm, which benefits you directly, is the logical outcome of everyone’s hard work and abilities. It was this conflation of the democratic responsibilities of lawyering with our position at the top of a highly profit-driven industry that rankled, and still does.

Because, despite all our good intentions, the country that we sought to improve kept getting worse. The legal system — that thing we were charged to protect — kept getting worse.

I graduated from law school in 2020. Even a casual observer could offhandedly name a few of the ways that the legal system has degraded since then, from the overturning of longstanding personal liberties in favor of academic canons of interpretation to the wholesale repurposing of the federal government for purely personal gains, and 100 other things that blanket our phones every day.

And when all of this happens at the same time that you see your colleagues — colleagues who happen to be some of the brightest legal minds in the country — doing their best to preserve the legal system’s integrity, it eventually forces you to stare into the face of an unavoidable truth: No matter how many individual good actors there are in a system, if the system they work in is broken, then the work that they do will only ever make things worse. Or to put it even more pointedly: If all the good lawyers are spending 99 percent of their time ensuring that our legal system will benefit a select few, then the other 1 percent of their time won’t make much of a difference.

When this truth finally led me to leave Big Law in 2025, along with far more selfish reasons — such as not wanting to count my life in six-minute increments — I did not anticipate that the universe would immediately validate my decision. But then President Trump decided to make an example of Big Law, and the industry’s response provided a vivid demonstration of just how broken the system underlying it was.

The executive orders that Mr. Trump began to issue in March 2025 that sought to punish various firms for associating with his political enemies should have been a no-brainer fight for Big Law. Not only were the orders facially unconstitutional — meaning the text itself plainly violated the First Amendment even without factual support — but they also exhibited the kind of shoddy lawyering that has become a Trump administration hallmark. Taking these orders down was the kind of case that one of my former bosses would have handed to me and expected me to win.

And yet the industry largely decided to settle. Only four firms, including WilmerHale, decided to take the administration to court; they did so successfully. By contrast, nine other Big Law firms chose to settle, including five of the country’s 10 top-ranked firms and the single largest law firm in the world with more than $10 billion in annual revenue. This provided the Trump administration with a host of early victories to leverage this past year, including nearly a billion dollars of free legal services that Mr. Trump has used to negotiate trade deals; an open-ended and early commitment to do away with diversity, equity and inclusion policies; and a demonstration from some of the country’s highest-paid lawyers that the best way to respond to government abuses of power is to settle.

What’s more, the lawyers did all this while also explaining, as the Paul, Weiss chair Brad Karp did to his colleagues, that their “century-long legacy of courageously standing up for fundamental rights and liberties, for fairness in the justice system and for our society’s most vulnerable individuals … will never be subject to negotiation or compromise.” This was referring to a settlement that, as a reminder, was decried by Deborah Pearlstein as hastening “America’s slide from a system of constitutional democracy” and by the law professors Avi Soifer, Judy McMorrow and Paul Tremblay as “shameful and alarming.” Talk about a statement of fact.

It would be difficult to find a more vivid demonstration of the way that Big Law has lost sight of the democratic ideals at the heart of the profession — except for the fact that 2025 was, financially, a fantastic year for the industry. So fantastic that the publication The American Lawyer had to raise the bar for what constitutes a “Super Rich” firm from $1.1 million in revenue per lawyer to $1.45 million. That “Super Rich” list includes both firms that capitulated and firms that fought — all in the same year that was “marked by relentless, direct attacks on the rule of law and our constitutional rights,” in the words of the American Constitution Society.

Something is off.

The health of the U.S. legal industry and the U.S. legal system are not one and the same. And Big Law, as the legal world’s economic center of gravity and the route through which most of the country’s top legal talent flows — look at the current Supreme Court, where every justice except Sonia Sotomayor and Clarence Thomas got through Big Law — is at the heart of the problem.

I wish I could identify a solution as easily. But I think that getting lawyers to acknowledge the problem would be a significant step. Despite the number of people who have called out these issues — I am far from the first to leave Big Law disenchanted — we lawyers still tend to be very resistant to admitting that our profession could be anything less than exalted.

I am sympathetic to that impulse, but I also think it is time to relinquish it. Because — to use a lawyerly turn — clinging to it blends the statement of fact with the argument in a way that prevents lawyers from seeing the world around us and what our democracy really needs. And what it needs desperately is a full and unsparing accounting of the legal industry that is supposed to be protecting the ideals at its heart.

Another concept from the legal world that sticks with me: the legal fiction. A legal fiction enables the law to apply to situations that it would otherwise not be able to; treating corporations as people in certain legal contexts is one common example. But I think there is an even broader set of ideas to which we should also apply it: lawyers’ conception of themselves.

It is a fiction to think that a legal landscape organized around the principle of concentrating power and profit can operate to the benefit of our democracy. It is a fiction to think that a few well-intentioned pro bono hours can compensate for the rest of the work that we do. It is a fiction to think that individual actors can compensate for the drift of a system that works tirelessly to entrench those in power. And it is a fiction to think that lawyers can still be carrying out, as Samuel Adams observed, “one rule of justice for rich and poor” when the real-world impact of the legal industry is anything but.

These are fictions that we lawyers buy into because it is useful for us to believe them. But the fact that they are useful does not make them true. And the sooner we lawyers acknowledge that, the sooner we can figure out a way to make the reality we have a little more like these fictions that we aspire to tell.

Whether that is a statement of fact or an argument, I leave up to you.

Matthew Wollin, a writer and a filmmaker, is the director of “The Skin of the Teeth.”

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The post When I Left Big Law, I Learned This appeared first on New York Times.

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