Captain Black is pleased to hear that Colonel Cathcart has volunteered the men for the lethal mission of bombing Bologna. Captain Black hates the men and gloats about their terrifying, violent task. He is extremely ambitious and had hoped to be promoted to squadron commander, but when Major Major is picked over him, he lapses into a deep depression, out of which the Bologna mission lifts him. Captain Black tries to get revenge on Major Major by initiating the Glorious Loyalty Oath Crusade, during which he forces all the men to swear elaborate oaths of loyalty before doing basic things like eating meals. He then refuses to let Major Major sign a loyalty oath and hopes, thereby, to make him appear disloyal. The Glorious Loyalty Oath Crusade is a major event in the camp until the fearsome Major —— de Coverley puts an end to it by hollering “Gimme eat!” in the mess hall without signing an oath.

It rains interminably before the Bologna mission, and the bombing run is delayed. The men all hope it will never stop raining. When it does, Yossarian moves the bomb line on the map so that the commanding officers will think that Bologna has already been captured. Yossarian also gives the entire squadron diarrhea by poisoning the food so that they won’t have to fly. The rain then starts again.

In the meantime, ex-P.F.C. Wintergreen tries to sell Yossarian a cigarette lighter, going into competition with Milo as a black-market trader. He is aghast that Milo has cornered the entire world market for Egyptian cotton but is unable to sell any of it. The men are terrified and miserable about having to bomb Bologna. Clevinger and Yossarian argue about whether it is Yossarian’s duty to bomb Bologna, and, by the middle of the second week of waiting, everyone in the squadron is as emaciated as Hungry Joe.

One night, Yossarian, Nately, and Dunbar go for a drunken drive with Chief White Halfoat; they crash a jeep and realize that it has stopped raining. Back in the tents, Hungry Joe is trying to shoot Huple’s cat, which has been giving him nightmares, and the men force Hungry Joe to fight the cat fairly. The cat runs away, and Hungry Joe is satisfied. When he goes back to sleep, however, he has another nightmare about the cat.

Major —— de Coverley is a daunting, majestic man with a lion’s mane of white hair, an eagle’s gaze, and a transparent eye patch. Everyone is afraid of him, and no one will talk to him. His sole duty is traveling to major cities captured by the Americans to rent rooms in which his men can take leave; he spends the rest of his time -playing horseshoes. Major —— de Coverley always manages to be photographed with the first wave of American troops moving into a city, a fact that perplexes both the enemy and the American commanders. He seems to be a force of nature, and yet Yossarian is able to fool him by moving the bomb line: Major —— de Coverley has traveled to enemy-controlled Bologna and has not yet returned. The narrator relates that Milo once approached —— de Coverley on the horseshoe range, successfully requesting authorization to import eggs on Air Force planes.

We also learn that Colonel Cathcart had attempted to give Yossarian a medal some time earlier. When Yossarian was brave, he had circled over a target twice in order to hit it, and, on the second pass, Kraft, a younger pilot from the division, had been killed by shrapnel. Not knowing how to rebuke Yossarian for his foolhardiness, the authorities decided to stave off criticism by giving him a medal.

The squadron finally receives the go-ahead to bomb Bologna, but by this time Yossarian does not feel like going over the target even once. He pretends that his plane’s intercom system is broken and orders his pilot, Kid Sampson, to turn back. They land at the deserted airfield just before dawn, feeling strangely morose. Yossarian takes a nap on the beach and wakes up when the planes fly back. Not a single plane has been hit. Yossarian thinks that cloud cover must have prevented them from bombing the city and that they will have to make another attempt, but he is wrong: facing no antiaircraft fire, the Americans bombed the city without incurring any losses.

Captain Piltchard and Captain Wren ineffectually reprimand Yossarian and his crew for turning back and inform the men that since they missed the ammunition dumps the first time, they will have to bomb Bologna again. Yossarian confidently flies in, assuming there will be no antiaircraft fire, and he is stunned when shrapnel begins firing up toward him through the skies. He furiously directs McWatt into evasive maneuvers and fights with the strangely cheerful Aarfy until the bombs are dropped. Yossarian does not die—though many other men in the squadron do—and the plane lands safely. Yossarian heads immediately for emergency rest leave in Rome.

Luciana is a beautiful Italian woman whom Yossarian meets at a bar in Rome. After he buys her dinner and dances with her, she agrees to sleep with him, but not right then—she will come to his room the next morning. She does, but then angrily refuses to sleep with Yossarian until she cleans his room, disgustedly calling him a pig. Finally, she lets him sleep with her. Afterward, Yossarian falls in love with her and asks her to marry him. She says she won’t marry him because he is crazy; she knows he is crazy because no one in his right mind would marry a girl who was not a virgin. She tells him about a scar she got when the Americans bombed her town.

Suddenly, Hungry Joe rushes in with his camera, and Yossarian and Luciana have to get dressed. Laughing, they go outside, where they part ways. Luciana gives Yossarian her number, telling him that she expects him to tear it up as soon as she leaves because she thinks that he is impressed with himself that such a pretty girl would sleep with him for free. He asks her why on earth he would do such a thing. As soon as she leaves, though, Yossarian, impressed with himself that such a pretty girl would sleep with him for free, tears up her number. Almost immediately he regrets doing so, and, after learning that Colonel Cathcart has raised the number of missions to forty, he makes the anguished decision to go straight to the hospital.

In this section, the disordered chronology functions as an instrument for building suspense. The lengthy digression about the Great Loyalty Oath Crusade interrupts the tense build-up to the Bologna mission, which occurs shortly before the scene at the beginning of the novel, when the number of required missions is still thirty-five. The Great Loyalty Oath Crusade story is ironic and funny; the Bologna mission is a dismal story told in terms of endless rain and growing worry. By breaking off the Bologna story in the middle to tell the exaggerated parable of the Loyalty Oath Crusade, Heller heightens the sense of uncertainty and anticipation surrounding the outcome of the Bologna mission. During the description of the actual bombing run to Bologna, however, Heller devotes a chapter almost entirely to a single event, without his usual digressions. This very detailed, vivid account of the attack makes time appear to move more slowly, trapping the reader in the same drawn-out terror as the characters. The earnest, straightforward manner in which the Bologna story is told is a signal that we are meant to take this episode seriously—that there is nothing funny about this aspect of war.

Although Catch-22 is written mostly from the perspective of a third-person narrator who describes what each of the characters is thinking, we hear mostly what is happening in Yossarian’s mind, and many of the observations about the absurdity of the war seem to be his own. So, despite the fact that each chapter of Catch-22 bears the name of a character described in that chapter, the narrative generally returns to Yossarian. A significant departure from this organizational method occurs in the chapter entitled “Bologna,” however: instead of operating as a largely humorous description of the nature and history of one of the novel’s characters, this chapter remains almost entirely in the present of the story, and Yossarian is forced to confront his desire to live at the expense of everything else. The chapter title itself—a place name rather than a person’s name—marks a shift from a satirical and humorous focus on the unwitting characters engaged in the war to a serious focus on the present reali-ties of the war.

Yossarian’s vague guilt about abandoning his friends reveals a weakness in his philosophy of self-preservation: he seems to have no qualms about abandoning the mission and thereby keeping himself alive, but he does care about his friends and feels a mild trepidation while he awaits their return. Up to this point, Yossarian’s sole goal in life has been survival at the expense of everything else: he has subjected himself and his squadron to various illnesses, refused to enjoy fruit because it might make him healthy, and endured rather unpleasant hospital stays—all for the sake of not having to fly missions. Yossarian faces a difficult dilemma: on one hand, caring for others is destructive in that it undermines his ability to try to save his own life; on the other hand, caring for others is the only thing that mitigates the impersonal hatred that Yossarian perceives directed toward him.

The interlude with Luciana provides a welcome respite from life in the camp on Pianosa, but it also illustrates the strain placed on male-female relationships by the war. Luciana and Yossarian seem legitimately drawn to one another, but their relationship is brief and almost wholly sexual. Hungry Joe’s interruption of their time together demonstrates the glaring lack of privacy in Yossarian’s life and highlights the difficulty of having meaningful relationships in wartime. Similarly, Yossarian’s tearing up of Luciana’s number constitutes an act of irrational, self-satisfied exuberance that seems part and parcel of the absurd ironies forced on him by the Catch-22 mentality of the war. He is so overwhelmed at the end of this section—after Bologna, after Luciana, and after he learns that the number of missions has been raised yet again—that he decides to check into the hospital, a place of relative sanity and safety.