Yossarian tells Dobbs he is finally ready to kill Cathcart. Dobbs, however, has flown 60 missions (the new requirement) and thinks Cathcart will send him home; therefore he has no reason to kill him. Yossarian is frustrated by Dobbs’ change of heart.
Dobbs’ quick change shows he was perhaps not crazy after all. Now that he’s flown his required number of missions, his reasons for killing Cathcart disappear.
Yossarian learns from Sergeant Knight that Orr had to crash-land his plane in the water while Yossarian was in the hospital during the last bombing run, but that Orr managed to save his whole crew by escaping on a life raft. Yossarian dreams of being shot down and guiding his plane safely into neutral territory: Switzerland, Majorca, or Sweden.
An important instance of foreshadowing. Yossarian’s daydreams of escape are often prompted by thoughts of Orr, who is the soldier most skilled at ditching his plane and floating around in a life raft, as this episode illustrates.
Yossarian returns to his tent and finds Orr, safely back, and tinkering again with the stove. Yossarian asks him not to work on it right now—he finds it annoying. Orr tells him he wants to fix up the stove in time to have it working for Yossarian in winter. Yossarian asks where Orr will be then—Orr doesn’t respond.
Yet more foreshadowing. Orr seems to be planning something here—perhaps a more serious escape from Pianosa. But Yossarian does not pick up on Orr’s hints—and he still can’t stand Orr’s efforts at fixing the stove, even though Yossarian will come to rely on that stove’s heat.
Orr tells Yossarian they should fly together, but Yossarian counters that Orr is shot down or has to ditch nearly every flight. Orr tries to tell the story of the woman who hit him in the head with a shoe in Rome, but Yossarian interrupts him. Yossarian begins thinking of all Orr’s skills—he is an incredible craftsman and handyman—but concludes that Orr is a “simpleton” who will be chewed up and spit out by the Army.
Here, Yossarian’s desire to remain alive actively thwarts his ability to escape Pianosa, in something like a catch-22. Because he doesn’t want to be shot down, he doesn’t fly with Orr, but it's not that Orr is a bad pilot—Orr is practicing getting shot down in order to escape. Thus if Yossarian were more willing to risk his life, he would be more readily able to escape.
Yossarian watches Orr fiddle with the very small components of the stove, and the two talk of prostitutes in Rome—including Captain Black, who sleeps with Nately’s girl in order to anger Nately. Orr asks, again, why Yossarian refuses to fly with him. Yossarian is embarrassed but evades the question. He doesn’t want to fly with Orr because he doesn’t want to be shot down.
It is never mentioned whether Black derives any pleasure whatever from sleeping with Nately’s prostitute. He appears to do so only to anger Nately—this is the true cause of his desire, and this is what keeps Black interested in the young woman.
Later, in another Bologna mission, Orr is shot down, ditches, and escapes in his own life raft that drifts away from the rest of the crew, who are in a separate raft. Kid Sampson tells Yossarian that Orr is missing. Yossarian expects Orr to return, and laughs to himself at the thought of Orr alone in his raft, paddling to shore. But Orr does not return at the end of the chapter; he remains missing.
Orr’s predictions for himself have come true. Although Orr seems to many of the officers like a “simpleton,” he is in fact the best long-range planner of them all. The trope of a supposed “idiot” who is actually quite crafty has a long history in literature, and Heller makes excellent use of the trope here.