Hollywood, 1937. Franklin Roosevelt was beginning his second term as president. The Great Depression, eight years in, still showed no signs of easing, with an unemployment rate of more than 14% and millions of Americans out of work. The economics of everyday life looked very different: Gasoline cost 10 cents per gallon, a car ran about $760, and a house could be had for roughly $4,000.
And, for a brief period in the late 1930s starting in 1937, F. Scott Fitzgerald was trying to make it in Hollywood. Things were going poorly. The preeminent writer of the Jazz Age was down on his luck—he had not had a hit in years, his wife was institutionalized, and alcohol was consuming him. “Bleak” would be an understatement.
At the time, most people had already forgotten the book for which he is now most celebrated, “The Great Gatsby,” which had been a financial disappointment upon its publication 12 years earlier. Only after Fitzgerald’s death, during World War II, did it become a classic, when the U.S. government printed mass editions for soldiers seeking moments of escape.
So here he was, living in Southern California and trying to eke out a living as a screenwriter. One might assume that a Princeton-educated, formerly best-selling author could find at least modest success in Tinseltown. Not so. Hollywood was a bust for Fitzgerald. His time there yielded only a single screen credit and a scattering of minor rewrites. He died a few years later in 1940, depressed and in debt, long before his genius was fully appreciated—a tragic end for the author of what is arguably the great American novel.
Yet, from this ignominious last chapter emerged a self-reflective work in which Fitzgerald briefly returned to an elevated artistic form, and left readers with an idea that still resonates nearly 90 years later.
Just before heading west, Fitzgerald penned a series of essays for the newly established Esquire magazine. In one of those essays, “The Crack-Up,” he laid bare the fractured state of his life, chronicling his mental breakdown, confronting the limits of his creative gifts, and groping toward some semblance of renewal. The series, like much of his later work, was poorly received at the time, though history has been kinder. What endures most is a single sentence familiar to nearly all of us; a sentence that demonstrated Fitzgerald’s rare ability to capture in a few words what others might spend volumes attempting to convey: “The test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.”
It is a simple statement, but like all great prose, its simplicity conceals profound complexity and insight.
Defining the Problem
For attorneys and litigation professionals, holding two opposing ideas in our minds at the same time is precisely what we are called upon to do. This means simultaneously advocating zealously for our clients while recognizing the legitimate interests and positions of opposing parties—a cognitive balancing act that many practitioners struggle to maintain. And yet, much of the way we currently practice cuts against this basic principle.
A few months ago, I was struck by Dr. Bill Kanasky’s CLM Magazine article, “The Cognitive Autopilot Problem,” and the way he explored why well-prepared witnesses often falter in depositions, arguing that the brain defaults to communication patterns that conflict with what attorneys and witness preparers aim to achieve. In short, human beings evolved to answer clearly and truthfully based on instinctive conversational norms. We, however, as litigators, want to interrupt that process by controlling how a witness answers.
Why? Because we’re trained to think in sound bites: How will it read on the transcript? Can it be used for cross? Will a mediator latch onto it?
This instinct to control and manipulate testimony, rather than help witnesses communicate truth effectively, exemplifies how zero-sum thinking corrupts even our most basic professional functions. We fight for every inch of strategic advantage in what often feels like trench warfare, where victories are measured in de minimis gains: We advanced four inches while you advanced three. In doing so, we drift from our ultimate task—to persuade.
Though it may not feel like it, we are in the persuasion business. Attorneys must persuade opposing counsel, judges, juries, co-workers, and insurers. Insurance professionals must persuade insureds, supervisors, and risk committees. Yet, during litigation, we often abandon persuasion and default to the “fight, fight, fight” mindset: weeks, months, and years spent tallying wins—this discovery dispute, that motion, this evidentiary ruling, that jury instruction. Everything becomes a scoreboard.
But what does it amount to?
This is the central question we should ask. If we are being honest with ourselves, many (if not most) of these tactics amount to very little. We tell ourselves they do—in mediation, we toss a few arguments against the wall hoping that our accumulated “litigation wins” somehow matter, but settlement decisions rarely hinge on these interim victories. The true calculus is exposure and costbenefit, not page 4,632 of document production or some inconsistency we have trapped the plaintiff into in the seventh hour of a deposition.
Pop culture gives us a useful contrast. The Paramount+ show, “Landman,” follows the intertwined lives of Texas oil executives and those orbiting them. One character, Rebecca Falcone (played by Kayla Wallace), is a ruthless corporate negotiator who breezes through conflicts with intimidating efficiency. In a recent episode, she is brought in to resolve a messy settlement involving drilling equipment. In a single, sharply edited scene, she demolishes the opposing side, pays nothing, highlights how the other side’s argument is meritless, and leaves victorious. She also receives a job offer on her way out of a gleaming boardroom. No spoilers here, but things get slightly more complicated as the season plays out.
In practice, most attorneys have better odds of winning Powerball than experiencing anything resembling that scene, but it still contains a kernel of truth: The matter was resolved not with years of litigation, mountains of documents, or endless discovery battles. Both sides cut through the posturing (well, most of it) and got to the heart of the issue. They danced a few rounds, and the framework of a deal emerged. That is a TV fantasy worth trying to approximate.
A Practical Framework
Our profession might benefit from adopting a positive-sum framework. We are well acquainted with zero-sum thinking: I win, you lose. Litigation often treats every disagreement as a finite contest, a modern analogue to huntergatherers fighting over scarce food, except instead of bear pelts and wolf carcasses, we have motions and depositions. We create artificial scarcity and treat each dispute as existential.
Positive-sum thinking, however, seeks outcomes in which both sides gain. We often employ this mindset at mediation, where mediators appear calm, sun-kissed, and somehow above the fray; seemingly fresh off a private jet from Maui while we crawl in from I-95 traffic in mid-January.
But what if we extended this mindset to pre-mediation litigation? Disputes need not be scored in inches. Instead, disagreements could be reframed as opportunities for both sides to build the record they believe necessary. Doing so would be a living example of Fitzgerald’s “first-rate intelligence”: holding two opposing ideas at once.
In truth, this is how many evidentiary issues are already resolved. Matters proceed most efficiently when counsel works out what can be agreed upon rather than waging war over every point and inundating the court with motions. The result, almost always, is a mixed bag: some wins, some losses; with the hope that the important issues fall on the right side of the ledger.
When defending any case, defense attorneys, insureds, and insurers need to spend time trying to understand what the other side really wants. And that is not always a dollar figure. When you know the answer, the next step should be how you can give the other side what it really wants while still maintaining your defense. It cannot just be: “I’m never paying you a dime!”
Positive-sum thinking, used judiciously and with reciprocal cooperation, can cut through the inertia of protracted litigation and present both sides with a more pragmatic, reasonable, and cost-effective path to resolution. Instead of framing litigation as a never ending battle, let’s look at it for what it is at its core: a series of problems we’re paid to solve. If we looked at the case like a problem solver, how many of these battles would we have really pursued? How much of the naturally situated antagonism would fade away?
Perhaps more importantly, what might this look like in practice? Instead of fighting over the scope of every deposition, counsel might agree upfront on reasonable time limits and topic areas, allowing both sides to develop their record efficiently. Rather than blanket objections to discovery requests, parties could meet and confer with genuine intent to provide relevant information while protecting legitimate privileges. At case management conferences, proposing joint stipulations on uncontested facts saves court resources and attorney time.
Of course, this approach requires a critical caveat: What if the other side exploits cooperation? This is a legitimate concern, and positive-sum thinking should not be confused with naïveté. Good-faith cooperation means being strategic about where collaboration makes sense while remaining prepared to advocate forcefully, when necessary. It means beginning with an extended hand while also being ready to defend vigorously if that hand is slapped away. The goal is not to become a doormat but to avoid unnecessary combat where both parties can advance their legitimate interests.
We cannot control what plaintiffs and their counsel will do. And with the billboard ads and television commercials piling up, we are likely justified in much of our revulsion toward the ambulancechasing aspects of our opponents. But the best way through may not be to force a protracted litigation arms race. It may be, at its core, to hold two ideas in our minds (that our clients are entitled to a defense, and the plaintiffs may have a point) and work through from that point forward.
Although the “two ideas” quote is the most famous line in Fitzgerald’s ”The Crack-Up,” the sentence that follows is equally relevant and perhaps even more poignant: “One should, for example, be able to see that things are hopeless and yet be determined to make them otherwise.”
A useful reminder for us all.
Matt Cianflone is general counsel at Gold Medal Bakery, Inc. mcianflone@ goldmedalbakery.com