In chapter seven we learn that McWatt, who is Yossarian's pilot, has had his prized bedsheet stolen. Lieutenant Milo Minderbinder, who is the mess officer, is in negotiations to get the sheet back. To do this he needs some pitted dates, which he can obtain from Yossarian. The plan is to offer the dates to the thief, who does not speak English, and take the bedsheet as the thief reaches for the dates. Milo rationalizes this act in this way: Since the thief does not speak English, he does not know if the dates are being offered as a bribe for the sheet or not, so therefore he is not cheating the thief. In the end Milo gets back the bedsheet, but he cuts it up into pieces. He gives some to Yossarian, takes some for himself and gives the rest to McWatt.

Chapter eight takes the reader back to Clevinger and Yossarian's cadet days, where Clevinger is seen as a know-it-all by everyone, especially to Lieutenant Scheisskopf , who is their drill sergeant. Lieutenant Scheisskopf has two driving forces in his life, one is to win the red pennant which denotes their squadron as the best squadron at parading before the reviewing stand, and the other is to bring Clevinger up on charges. He feels that Clevinger is a "troublemaker and a wise guy." Scheisskopf could not figure out how to get his men to march in a fashion which would allow them to win the red pennant. Scheisskopf finally does two things to help him win - he allows the men to choose their own cadet officers and he comes up with a style of marching in which the soldiers' hands only moved three inches back and forth. This wins them the red pennant permanently and puts an end to the parade march competition.

Lieutenant Scheisskopf also finds a series of charges to levy against Clevinger after Clevinger had the misfortune of stumbling while he was marching. Clevinger is brought before the Action Board and was tried with Scheisskopf as a judge, prosecutor, and defender. There are two other members of the board who also preside over this mockery of a trial. Needless to say, Clevinger is found guilty and sentenced to punishment tours.

Major Major Major was named so by his father as a joke. It was no joke to Major Major; all it did was ostracize him and cause him a great deal of hardship. He is a problem for Colonel Cathcart because he does not like having two majors in the squadron, so when Major Duluth is killed, Major Major Major is promoted to squadron commander. Just as he is starting to make friends, he is once again without friends because now he is everyone's boss. Most of his day is taken up by signing papers about a pilot who died in battle two hours after arriving at the base. He was never put on the official rolls so it appeared that he had simply vanished. Major Major is also given a large quantity of papers to sign dealing with matters he is not conversant with. He is only required to sign his name, so out of boredom he begins signing Washington Irving's name to the documents. The result is the appearance of a second C.I.D. man who suspects everyone from Sergeant Towser, Major Major's secretary, to the squadron chaplain of signing the papers. Finally, out of pure frustration with the situation, Major Major instructs Sergeant Towser to only allow people in his office when he was out of his office. This way he no longer has to deal with anyone.

Clevinger has died in a milk run off the coast of Elba. No one knows what had happened to him. Yossarian thinks Clevinger's disappearance is like that of a barracks of men who had disappeared at Lowery Field, but now he realizes that Clevenger is really dead. He is talking to ex-P.F.C. Wintergreen, who is constantly in trouble for going AWOL. His punishment is to dig holes. Wintergreen doesn't see how the disappearance of 64 men is exciting but, to Yossarian it gives him hope that he too could one day escape from the war.

The men have been volunteered by Colonel Cathcart to bomb ammunition dumps in Bologna. To the men it is a death run, and no one wants to go. In order to have enough men available to fly the bombers the medical tent is closed. This way no one can be declared unfit to fly.

In chapter eleven the character of Captain Black, intelligence officer is introduced. He is opposed to Major Major because he felt the command of the squadron should have been his after the death of Major Duluth. When he finds out the men are going to Bologna he is thrilled because he wants the men to be afraid. He reminisces about his loyalty oath campaign. It made him feel important because the men were afraid of him then. Captain Black decided that Major Major is a Communist and to prove it he is going to make everyone sign a loyalty oath except Major Major. He not only makes them sign a loyalty oath for anything they needed, but they also have to recite the Pledge of Allegiance and sing the Star Spangled Banner to receive food. He got away with this until the executive officer Major______ de Coverly put a stop to it.

Chapters seven to eleven tell us how Major Major became the squadron commander and how Milo got back McWatt's sheet. It also gives us insight into the lengths Captain Black will go to exact revenge on Major Major. Scheisskopf's need for recognition and his hatred of Clevinger are also explored. Heller shows us how commanders have very little regard for the lives of their men by Cathcart volunteering his men for a dangerous mission.