As the story progresses, amusing antics turn grim. The squadron's mess (dining hall) officer is an entrepreneurial whiz named Milo Minderbinder, whose capitalistic expertise is satirically entertaining until it turns deadly. Using squadron funds to purchase black-market products, Milo builds an enormous syndicate dealing in everything from fresh eggs to prostitutes. He eventually contracts with both sides in the conduct of the war and goes so far as to arrange an air raid on his own base for profit. McWatt's buzzing of the beach is a practical joke until one day when he slices Kid Sampson in two in a macabre accident. Nately's devotion to his prostitute seems like an innocent young man's harmless crush until he insists on flying extra missions so that he can stay near her — and is killed the next time out.
Nately's death serves as a transition to the end of the novel. When Yossarian reports the tragedy to the young man's prostitute-fiancée in Rome, she directs all her frustration and anger toward Yossarian, attacking him repeatedly, even after he returns to Pianosa. Yossarian has refused to fly further missions. Colonels Cathcart and Korn call him in for a conference in which they offer Yossarian a "deal": He can return home if only he will speak well of the commanding officers and turn his back on the men of the squadron. Yossarian agrees. Leaving the office, he is again assaulted by Nately's fiancée and seriously wounded. In the hospital, Yossarian reflects on all his friends who have died or disappeared during the year. He decides to renege on the agreement even though he is thus eligible for court-martial. Yossarian's plan is to rescue Nately's kid sister from the streets of Rome and flee to Sweden where his buddy Orr has turned up after cleverly using his plane crash as a means of escape. Yossarian hopes to find himself by losing himself, to seek a separate peace, to run toward life by escaping the madness of war.
