Greene argues that strategic power is derived from disorienting an adversary by violating their expectations of proper conflict sequence. He asserts that, where behavior conforms to patterns of normalcy, an adversary feels secure, but where it violates these patterns, they are disoriented by confusion and emotional disruption. He emphasizes that, for unpredictability to be most effective, it must be an intentional interplay of the normal and the extraordinary, first establishing, then violating expectations.

Greene cites Hannibal’s wars with Rome to illustrate the central argument of the chapter. Hannibal’s crossing of the Alps, his deceptive retreats, his ambushes at Trebia and Trasimene, and his pretended weakness, which led to Cannae’s encircling of his army, all demonstrate how his repeated violation of expectations led to the Romans’ defeat. Similar principles are demonstrated by Alexander the Great’s pretended inactivity along the banks of the Hydaspes River, which lulled his enemies into complacency. During General Ulysses S. Grant’s campaign against Vicksburg during the American Civil War, he violated Confederate expectations by using unconventional means to supply his army. Muhammad Ali’s fights with Sonny Liston demonstrate how a calculated display of unpredictability, psychological provocation, unconventional movement, and precision disoriented the larger, physically stronger opponent.

The chapter incorporates events in military and cultural history in which rules had become so codified that they ceased to be rules and became blinders. However, Greene assumes that strategists are aware of this tendency and can break their own rules, an assumption that privileges an individual’s role over the rules governed by institutions, which may not be applicable in a bureaucratic or conservative system. In drawing attention to the fluid interplay between the ordinary and the extraordinary, Greene suggests that strategic advantage is not necessarily about the pursuit of constant innovation, but about recognizing the point at which convention itself has become the main barrier.

Greene argues that the concept of moral legitimacy is present in every form of conflict, both social and political. He asserts that power is never maintained solely through force, but is always dependent on the perception of justice, righteousness, and motive. He redefines the concept of morality as a terrain to be occupied, defended, or abandoned, rather than a goal to be achieved. He believes that those who are able to define their cause as legitimate are given more room to maneuver, while those who are defined as immoral, hypocritical, or power-driven are given fewer options. He explains that the element of moral high ground must be created, not simply assumed.

Greene defines the theological debate between Martin Luther and Pope Leo X  as a public indictment of the Catholic Church on the basis of morality, presenting it as a quintessential example of a moral offensive. He explains how Luther used the printing press, inflammatory rhetoric, and calculated integrity, such as not accepting payment for his writing, to position himself as righteous and force the Catholic Church to overreact, thereby increasing his own legitimacy. Greene reinforces this argument by citing the work of US military strategist John Boyd and French military officer André Beaufre on the use of morality to gain a stronger position in war.

One of the major tensions in the chapter revolves around Greene’s readiness to embrace morality as an entirely instrumental resource, separate from ethical commitment and deployable at will. The historical cases he cites demonstrate the ways morality can mobilize support and create obstacles for opponents, but Greene’s suggestion to exploit guilt, outrage, and victimhood over authenticity and good faith negotiations assumes that moral credibility is an entirely manipulatable resource. Such an assumption overlooks the potential instability of such a strategy, as moral authority quickly dissolves once the strategic intent of such manipulation becomes clear. While the chapter offers insight into the efficacy of moral warfare, it leaves the question of whether such a resource is strategically sustainable uninterrogated.

In this chapter, Greene examines guerrilla warfare as a psychological approach to conflict. He focuses on a strategy he refers to as “the void,” or the refusal to engage in direct battle in favor of indirect tactics that force an opponent into a suboptimal position. He asserts that enemies, especially strong and aggressive ones, expect contact, engagement, and decisive battles. By avoiding battles, spreading out, and remaining elusive, a weaker opponent can create a void that forces the stronger opponent lose time and strategic edge. According to Greene, victory does not only result from defeating an opponent in battle, but also from besting them psychologically.

Greene supports his argument by referencing Napoleon’s invasion of Russia in 1812. Czar Alexander I’s strategy of retreat, scorched earth, and harassment left Napoleon unable to engage in a decisive battle and lacking supplies, forcing him to move deeper into the enemy’s territory, where frustration and overconfidence distorted his strategic thinking. Greene provides information on the history of guerrilla warfare, citing the Spanish resistance in the Peninsular War, the Cossacks who fought the French invasion of Russia, and later revolutionary strategies that emphasized dispersion, patience, and political mobilization as key warfare tactics. He demonstrates the non-military relevance of this strategy with the example of Franklin D. Roosevelt’s evasive, media-based political strategies.

Greene’s arguments refer to historical periods in which the use of asymmetric war strategies emerged as a response to imperialism, massive armies, and bureaucratic rigidity. The author’s focus on the psychological effects of the void, rather than the ethical ones, prioritizes strategic efficacy over the humanitarian consequences. However, the strategy remains relevant to contemporary political, virtual, and organizational conflicts, where evasion, fragmentation, and a refusal to engage in direct conflict threaten the stability of institutionalized powers.