Tactical Lessons from Sun Tzu for the Modern Litigator

In the second part of this series, we turn from foundational strategy to more tactical guidance drawn from The Art of War.

The following five maxims illuminate when to press a point, when to hold back, and how to manage the tempo and scope of litigation in a way that serves the client’s real interests.

“He will win who knows when to fight and when not to fight.”

• Text and chapter: “He will win who knows when to fight and when not to fight.” – Chapter 3, Attack by Stratagem.
• Litigation lesson: Discretion is a strategic tool; declining to pursue marginal claims, unnecessary motions, or low‑probability appeals can protect client resources, preserve credibility with the court, and avoid creating unfavorable precedent.

“Speed is the essence of war.”

• Text and chapter: “Speed is the essence of war. Take advantage of the enemy’s unreadiness, make your way by unexpected routes, and attack unguarded spots.” – Chapter 11, The Nine Situations.
• Litigation lesson: Timely action—rapid filing to secure venue, striking affirmative defenses, early requests for injunctive relief, prompt dispositive motions, and efficient discovery—can seize momentum, frame the narrative for the court, and limit the opponent’s opportunity to regroup.

“The rule is, not to besiege walled cities if it can possibly be avoided.”

• Text and chapter: “The rule is, not to besiege walled cities if it can possibly be avoided. The preparation of mantlets, movable shelters, and various implements of war, will take up three whole months; and the piling up of mounds over against the walls will take three months more.” – Chapter 3, Attack by Stratagem.
• Litigation lesson: Some litigation tactics—like sprawling discovery wars, satellite proceedings, or “kitchen sink” motion practice—are the procedural equivalent of a siege: slow, costly, and uncertain. Strategic counsel favor narrower, higher‑yield avenues that advance the client’s objectives without needlessly consuming time and money. Moreover, in the age of proportional discovery, such tactics are disfavored and may subject a litigant to sanctions.

“There are roads which must not be followed…”

• Text and chapter: “There are roads which must not be followed, armies which must not be attacked, walled cities which must not be besieged, positions which must not be contested, commands of the sovereign which must not be obeyed.” – Chapter 8, Variation in Tactics.
• Litigation lesson: Even when a tactic is legally available, it may be unwise or unethical: pursuing personal attacks, threatening criminal prosecution, using litigation primarily for harassment, or pressing arguments that undermine broader client interests can damage both your case and your reputation more than they help.

“He will win who, prepared himself, waits to take the enemy unprepared.”

• Text and chapter: “He will win who, prepared himself, waits to take the enemy unprepared.” – Chapter 3, Attack by Stratagem.
• Litigation lesson: Thorough preparation—mastery of the record, law, evidentiary issues, and settlement alternatives—puts you in position to capitalize when the other side overreaches, fails to prepare a witness, or misjudges the court’s concerns at a key hearing or trial.

Closing Note

This series is not intended to trivialize the realities of war or to suggest that disputes in litigation are comparable to the grave risks and loss of life that armed conflict entails; war involves physical danger and human suffering that have no true analogue in civil disputes.

Rather, these posts recognize that The Art of War has long been read as a work of strategic and philosophical reflection whose insights into planning, conflict management, and human psychology can inform many forms of non‑violent conflict, including the orderly resolution of legal controversies.

Sun Tzu’s recurring theme—that the best victories are those achieved with the least harm and, where possible, without fighting at all—underscores that the highest form of strategy is to resolve conflict wisely, a lesson that remains highly relevant for lawyers seeking just, efficient, and humane outcomes for their clients today.