First, two truths:
- Practicing law is hard.
- Playing chess is harder.
How do we know this?
Because lawyers love to compare litigation to chess.
And because, in the recorded history of all of humankind, no chess master has ever compared what they do to practicing law.
Not one.
Lawyers compare litigation to chess in CLE presentations, at law firm retreats, during client pitches, and in countless office conversations. The analogy has become shorthand to convey intelligence itself: think three moves ahead, sacrifice a pawn, anticipate the counterattack.
The analogy is also one of the profession’s most persistent myths.
If litigation is a game—not in the frivolous sense, but in more of a mathematical sense—it is little like chess.
In chess, the board never changes. Every piece is visible. The rules are fixed. No one discovers halfway through a match that the rook neglected to mention an inconvenient fact. The queen does not suddenly produce a previously undisclosed email. The king never announces, late in the match, that he has remembered “one small thing” that changes everything. The knight doesn’t change his story or forget everything.
The opponent does not suddenly decide that the game is no longer worth playing.
The pieces do not have competing interests.
And no one is paying $1,000 an hour to advise the players about whether they should keep playing.
Litigation operates under different rules entirely. It is played with incomplete information, asymmetric knowledge, changing incentives, and imperfect communication.
Game theory explains why.
Chess is the classic example of a game with perfect information. Every player knows every available move and sees every piece on an unchanging board. Victory belongs largely to the player who calculates more accurately.
Even elite chess players rely in practice on intuition, pattern recognition, and psychology—the game tree is too vast for pure calculation. But the critical distinction is not the difficulty of calculation; it is the fundamental asymmetry of information. In chess, both players see the same board.
Litigation offers no such clarity. The most valuable facts are often the ones no one has uncovered yet. Every participant knows something no one else does. Clients omit details they think are unimportant, problematic, or embarrassing. Opposing counsel may reveal no more than the rules require. Judges have preferences that become apparent only after several hearings. And the most important players—jurors—do not even appear until late in the game, their inherent differences adding yet another layer of unpredictability.
The board isn’t merely hidden in litigation.
Parts of it are still being built while everyone is playing.
And the players can change their minds.
Consider the California Supreme Court’s recent decision in Gorobets v. Jaguar Land Rover North America. In that case, the defendant made the plaintiff a statutory offer to compromise under California Code of Civil Procedure section 998. The offer gave the plaintiff two alternative ways to resolve the case, including an $85,000 lump-sum payment. The plaintiff rejected the offer and went to trial. The jury awarded him $76,155.27—less than the $85,000 alternative.
The legal question was whether a statutory offer of compromise containing alternative choices could be sufficiently certain to trigger section 998’s cost-shifting provisions. The California Supreme Court held that it could, rejecting the idea that giving the plaintiff alternatives necessarily made the offer too uncertain.
But the more interesting part of Gorobets is what happened before the legal question reached the Supreme Court.
The plaintiff had a choice.
Take the offer or keep playing.
A chess player doesn’t face that kind of decision. The board is visible. The pieces are known. The consequences of a move can, at least in theory, be calculated.
The plaintiff in Gorobets had no such luxury. He knew the settlement offer. He knew his own case. But he did not know what the jury would do. Neither did his lawyer. Neither did the defendant.
He had to make a decision with incomplete information.
That is not chess. That is poker.
Poker players do not know what card will come next. They know the cards they hold, they know some of the cards on the table, and they try to determine what their opponents may be holding. They assess probabilities. They weigh risk against reward. They watch the other players. And then they decide whether to bet, call, raise—or fold.
Litigators do essentially the same thing.
A settlement offer is a bet. A rejection is a bet. A motion is a bet. Taking a case to trial is, often, a very, very large bet.
And a trial lawyer is constantly asking a question that a chess player almost never has to ask: What are the odds that I’m wrong?
That question is at the heart of Gorobets. The plaintiff was not deciding whether he could win. He was deciding whether he was sufficiently confident that he could win more than the settlement offer to justify rejecting a guaranteed result.
That is a very different calculation—it is a poker calculation.
The same is true on the other side. Jaguar Land Rover was not simply calculating whether it could defeat the plaintiff at trial. It was trying to influence the plaintiff’s calculation. By making the statutory offer of compromise, it was effectively saying: Here is the amount you can take off the table now. If you choose to keep playing, you are betting that you can do better.
That is game theory in action.
Now consider a party deciding whether to file a motion in limine to exclude the opposing party’s expert testimony.
The motion might succeed and gut the opponent’s case before trial.
Or it might fail and telegraph your trial strategy, revealing exactly which weakness you fear the judge and jury will see.
The party must act without knowing how the judge will rule, how the expert will perform under cross-examination, or whether the jury will accept the testimony.
That is another poker decision, not a chess one.
The genius of poker is that a player can make the correct decision and still lose.
You can have the better hand and lose to the next card. You can fold and later discover that you would have won. You can call a bet, lose the hand, and still have made the mathematically correct decision based on the information available at the time.
Litigation works the same way.
A plaintiff can reject a reasonable settlement offer and win. A different plaintiff can reject the same offer and lose. A defendant can make what looks like a reasonable settlement offer and still end up paying more at trial. A lawyer can recommend settlement, the client can reject it, and the case can produce exactly the result the lawyer feared.
None of those outcomes necessarily tells us whether the decision was good.
That is one of the hardest things about litigation. We judge decisions by their outcomes even though the decisions had to be made before the outcomes were known.
Chess makes that problem seem simpler. If you lose a chess game, you can usually identify the move that went wrong. Litigation is rarely so accommodating. Sometimes the decision that looks foolish in retrospect was completely rational when it was made. Sometimes the decision that produced a spectacular victory was actually a terrible decision that happened to work.
The best litigators understand the difference.
They don’t ask only, Did we win?
They ask, Did we make the best decision with the information we had?
That is the language of probability. And of poker.
Game theory teaches that strategy is really about incentives. In litigation, that means asking uncomfortable questions.
Why won’t the other side settle?
Why did a cooperative witness suddenly become hostile?
Why is a corporation willing to spend a significant amount of money litigating a case worth half that amount?
Why did the plaintiff reject what seems like a perfectly reasonable offer?
Why is the defendant refusing to increase its offer by $50,000 when it has already spent ten times that amount in legal fees?
The answers are rarely found in legal doctrine alone. They lie in understanding what each participant believes, fears, values, and hopes to accomplish.
Some things in litigation may be predictable. But people are not. A plaintiff may care more about principles than money. A defendant may gladly absorb significant legal fees to clear its name and discourage future claims. A witness may testify inaccurately not because they are dishonest, but because they are nervous or their memory is imperfect. A client may reject a settlement because accepting it feels like admitting defeat. A lawyer may recommend settlement because the numbers make sense while the client refuses because the numbers aren’t the point.
None of this happens on a chessboard.
Yet it happens every day in litigation.
To be sure, the chess analogy survives because it flatters lawyers. It suggests that success belongs to whoever possesses the highest IQ or sees the farthest ahead. It reduces defeat to a failure of calculation.
Litigation is messier.
The most successful litigators are not masters of prediction. They are masters of adapting. They absorb new information without clinging to old assumptions. They revise their strategies. They persuade instead of merely calculating. They recognize that credibility, timing, relationships, and psychology often determine outcomes every bit as much as legal analysis can.
They also understand that their opponent is not a chess piece. Their opponent is a person—one who can become angry or frightened or overconfident, change lawyers, change their mind, or receive the same information you received and reach an entirely different conclusion.
That last point is particularly important. Litigation isn’t merely a contest between two sides with different information. It is a contest between two sides with different interpretations of the same information.
The same deposition can be devastating to one lawyer and reassuring to another. The same expert report can make one side want to settle and the other side want to try the case.
There is no equivalent in chess. A bishop on a particular square means the same thing to both players.
Unlike chess, poker is a game of incomplete information. Each player knows only part of the story. Success depends on probabilities rather than certainty, on reading incentives rather than simply reading rules, on recognizing when to press an advantage and—just as importantly—when to fold a losing hand before pride becomes expensive.
Even the poker analogy has limits: poker involves a known deck and calculable odds, while litigation often involves risks that are not merely unknown but unknowable—a change in the law, a surprise witness, or a judge’s undisclosed bias. Still, poker remains the better fit because litigators must act on what they know while accounting for what they cannot know.
Like the best lawyers, the best poker players do not win every hand. They consistently make the best decisions with the information available at the moment.
That is what litigators do.
They do not calculate the next dozen moves on a perfectly ordered board. They make thoughtful decisions in an imperfect world where the facts evolve, the incentives shift, witnesses surprise them, judges see things differently, and every participant believes that they—and only they—are the rational actor.
Sometimes the smartest move is to press forward.
Sometimes it is to settle.
Sometimes it is to walk away.
Sometimes it is to change the strategy completely.
And sometimes it is to recognize that the person sitting across the table has a different idea of what constitutes winning.
The great chess player wins by seeing farther ahead.
The great litigator wins by understanding that the future is not entirely visible.
Chess rewards calculation.
Poker rewards judgment under uncertainty.
Litigation looks like chess when the task is pure legal-standards analysis, procedural sequencing, or statutory interpretation.
It looks like poker when the task is settlement negotiations, witness management, jury persuasion, or reading the opponent’s incentives.
Litigation requires both—but it looks a lot more like the second.
Chess is a beautiful game.
Litigation is a human one.
