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Judge Banner sends the sick Roy to a local maternity hospital, where the Judge has a special moneysaving contract. There the doctors consider taking Roy's appendix out, only to discover that it was taken out long ago "along with some other stuff." Roy has scars all along his body. He spends his nights groaning and delirious and his days using brooms and plungers to practice swings in front of a mirror. Finally he is tied down to his bed, while the Knights drop three games to the Reds, tying the Pirates in the standings. This means that the Knights and the Pirates will have to play a single playoff game for the pennant.
The doctor tells Roy that he can play in the game, but that afterward he should consider quitting baseball, or else he might die. Roy spends several terrified hours thinking only of death, refusing all his visitors. He then decides that the doctor might be wrong, so he sneaks out for a few practice swings at the field. Roy passes out at the plate, so the other players send him back to the hospital, where he has a delirious dream about Sam Simpson. When he wakes, he asks the doctor not to tell anyone—even Memo—about how sick he is.
Roy then tries to think about getting another job after baseball, but nothing he can think of would make enough money to keep a girl like Memo satisfied. His mind skips "from money to Memo." Memo herself comes to visit Roy, bringing flowers. Pop has greatly reprimanded Memo, who says she "sick of this life" and wants to escape. Roy asks her to marry him, but she asks him if he truly wants her. She tells him that she is afraid to be poor. She wants a house, a maid, a car, and a fur coat. Roy, she says, has to face reality: he is thirty-five and does not have much time left as a ballplayer. Roy tells Memo he could scrounge up $25,000 in a few months and then start a business. But Memo wants him to buy into a company where he could have an executive job and would not have to go "poking his nose into the stew in a smelly restaurant." Memo tells him it would take $50,000 to get into a company like that. Roy thinks about this and then realizes that Memo has been sent by someone—the Judge, she reveals. The Judge and Gus Sands want to pay Roy off to throw the playoff game. Roy refuses, and Memo leaves.
Later, the Judge visits Roy in the hospital. He offers Roy money to drop the pennant game. Roy haggles about the price, trying to decide whether he would be able to play or not; if he were able to finish a World Series and make it to the end, he would have endorsement offers and probably a much greater salary. Meanwhile, the Judge tells Roy stories of how bad actions can sometimes have good consequences, and vice versa. Finally, Roy decides to sell out, getting the Judge to agree to a payout of $35,000, with a contract for $45,000 for the following year.
Memo returns and kisses Roy, calling him wonderful. She leaves, and then Roy finally reads Iris's letter. In the letter, Iris tells of how she dealt with having a child so young, and then having her own child marry and have a child, and how free that made Iris feel. Roy crumples the letter and throws it away.
In this chapter, Roy is faced with a choice between fulfilling the role that the mythological underpinnings of the novel requires of him—that of being the hero, like Perceval, who heals the Waste Land through the proper use of his talent—or to selfishly pursue his own misguided goals. In mythological terms, this section represents a trial of temptation for Roy's Perceval-like character. Unfortunately, we are likely aware by now that Roy does not have much strength of character. He is ultimately a coward, refusing to accept the responsibility that comes with the happiness of a relationship with Iris. Instead, Roy wants to run to the destructive, insubstantial "love" of Memo. Memo does not even offer Roy physical love; she spurns his every advance. Yet, in his stubbornness, Roy repeatedly attempts to win her through some method or another. One critic has referred to Roy as a "virtual buffoon"; nowhere does the accusation fit better than this chapter. It is painful to watch Roy make so many decisions that are clearly the wrong ones. Roy ruminates over the American Dream—fame and wealth—and wants Memo to be part of that. Indeed, Memo is the perfect complement to the American Dream; as one literary critic puts it, she is the "Bitch-Goddess of the American Dream," the trophy wife whose husband must maintain constant wealth and power to keep her. For Memo, Roy must be no less than a rich executive in order to provide the kind of lifestyle she wants. It is not difficult, however, for us to read between the lines and realize that even if Roy succeeded, his chances of being with Memo are slim; she is clearly playing him for the Gus Sands's benefit alone.
Roy's negotiation with the Judge is all the more infuriating because Roy clearly has a hint of what is going on. He shrewdly balances the benefits of selling out against the odds of doing well at the game and making it through one more season. Sadly, Roy never considers playing the game simply for the sake of winning the pennant, or for Pop Fisher, or even simply for a love of baseball. Indeed, Roy even gets angry with Pop because Pop reprimands Memo. Roy only considers his decision in terms of which option would bring him more money, and therefore win him Memo (he thinks). Memo is Roy's one true blind spot. His desire for is so unbelievably single-minded that it can be considered Roy's tragic flaw. Many of Roy's self-centered desires—wealth and, to a lesser degree, fame—fall by the wayside as he goes through the novel, but his desperate need for Memo (rather than the loving, caring Iris) remains long enough to bring him down.
The final sections and outcome of The Natural are almost maddeningly enigmatic. It is up for debate whether Malamud, after modeling his story on vegetative myths and the story of the Fisher King, abandons these underpinnings (and his characters) in the end. It might even be said that the two myths are in opposition to one another: Roy completely fails in obtaining the Holy Grail (the pennant) for Pop Fisher (the Fisher King), but he comes very close to achieving it—he is stopped only by the pitcher Youngberry, the next vegetative god, who puts Roy away just as Roy put away the Whammer fifteen years before. Finally, it is worth noting that the story of Perceval—upon which Malamud partially models his novel—written in the twelfth century by a French noble named Chrétien de Troyes, was unfinished. Chrétien modeled his own version of the story on earlier Celtic stories, and so scholars are confident in predicting that Perceval, after failing one time, eventually achieves the Grail—the outcome that occurs in earlier versions of the story. However, there is no reason to assume that Chrétien's finished version would necessarily follow the same pattern as the earlier texts. Indeed, in writing The Natural, Malamud writes his own ending to Chrétien's story. Malamud's is a somewhat pessimistic ending, suggesting that real heroes can only exist in fairy tales. However, as Roy does learn from his suffering, there is also some hope for everyone who is not a "natural."