Lieutenant Nately is an ingenuous nineteen-year-old, from a privileged background, who is in love with a Roman prostitute whom he hopes to marry. For her part, the young woman is, at this point in the novel, indifferent toward her suitor and interested only in her profession. Nately spends a great deal of money on the prostitute, eventually winding up at a tenement brothel with her, some of his friends, a "proliferating flow of supple young naked girls" and an "evil and debauched ugly old man" who seems to be in charge. Nately and the old man discuss the nature of war and the meaning of life. Meanwhile, Milo's syndicate has become increasingly international. On a typical day, he flies to England to pick up a load of Turkish halvah and returns by way of Madagascar with four Nazi bombers filled with fresh vegetables. He marks out the swastikas and stencils in "M & M Enterprises, Fine Fruits and Produce." The "M & M" stands for Milo Minderbinder, of course; but he thinks that initials make the syndicate look more widely controlled. His deals with the Germans complicate life for the squadron and nearly ruin the syndicate.
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