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Duddy is desperate to get his hands on money to buy up the rest of the land. He tries Jerry Dingleman first. He meets with the Boy Wonder to blackmail him, reminding Dingleman that he smuggled drugs for him and he knows what’s in all those suitcases he’s been bringing into the country and would be ready to say so in court. Dingleman calls Duddy’s bluff, though, reminding Duddy that technically he was the one who brought in the drugs that time, that he was the one carrying the suitcase. Duddy isn’t too concerned about that, saying that he was just a naïve minor, after all, being manipulated by a powerful older man. Then Dingleman tells Duddy that he saw his illegal pinball machines at various hotels. He thinks maybe the police would like to know about that. This derails all of Duddy’s efforts to get money out of the Boy Wonder.
Next, Duddy goes to his brother, Lennie, who offers Duddy all he has but it only adds up to $80. Lennie says he will ask their father for him because Max always preferred Lennie. Max sees right through the rouse and knows the request is for Duddy. To Duddy’s great surprise, his father agrees to loan him a thousand dollars, though Max says he is likely just wasting his money. Next Duddy attempts to get money by selling the belongings in his uncle’s house, where he, Yvette, and Virgil have taken up residence. Yvette is horrified and thinks it is an offense to his uncle’s memory, but Duddy is unfazed. He still hasn’t reached the needed dollar amount, so he calls Hugh Calder only to find out that their relationship has completely fizzled out. Duddy has only one more possible connection to cash, and that is Virgil. Virgil, he finds out, has money that has been left to him by his grandfather. It has been enough to pay his medical bills and set him up comfortably. When Duddy asks Virgil for a loan, Virgil gets hysterical and shouts that no, he can’t, that he promised Yvette he wouldn’t. Yvette hears the yelling and comes running, but Duddy refuses to admit that he asked Virgil for money, and Virgil won’t tell on Duddy. Duddy instead sneaks off and finds Virgil’s checkbook. He looks at the bank balance, whistles, and helps himself to two checks. He carefully forges Virgil’s signature and is feeling jubilant until Yvette screams and calls for him. Virgil has had another seizure and is bloodied and slumped over on the floor.
Duddy has successfully purchased all of the lakefront land, courtesy of the money he stole from Virgil. He travels there with Lennie, Simcha, and Max, in the hopes of impressing his grandfather. When the family arrives, Dingleman and Linda are also on the property, and they taunt Duddy. Duddy responds by calling both of them names and shouting that they are trespassing. Max tries to calm Duddy down but to no avail. What makes Duddy stop fighting with Dingleman and Linda is the sight of his grandfather getting back into the car.
Duddy chases after his grandfather, desperate for his approval. He tells Simcha that he did just as he told him. He got land. He has become a man. But Simcha fails to be impressed and doesn’t want to even speak to Duddy. When Duddy tries to address him, Simcha turns and gazes blankly out the window. With some cajoling, Simcha tells Duddy that Yvette came to see him. She told Simcha how Duddy got the money, that he swindled his epileptic, wheelchair-bound friend. Simcha tells Duddy that he will stay in the car, that he won’t set foot on his land. Max and Lennie have no idea what’s going on, so they decide a meal to celebrate is in order. Unaware of how Duddy got the money, Max and Lennie reassure Duddy that Simcha will come around, that he’s just being an ornery old man. Duddy knows the truth, though, and when he runs into Yvette outside the restaurant, he is not able to satisfactorily get the last word. Yvette tells Duddy that she wanted to sue him, but Virgil refused, that all he wants is to never see Duddy again. She tells Duddy it’s over, that she and Virgil are out of his life for good. Duddy walks into the restaurant after yelling that she’ll come crawling back some day. Everyone around him is ready to celebrate, but Duddy just asks for the bus fare back home.
Duddy commits an unforgivable transgression. He wrongs the person who is most loyal to him, Virgil. Signs that Duddy is willing to go this far are apparent throughout the novel and especially in this section. Duddy attempts blackmail, seeking out Dingleman and threatening to testify against him. He moves into his deceased uncle’s house, but rather than honoring his uncle’s memory, he sells every single scrap of furniture so there is barely enough for Virgil, Yvette, and him to comfortably live in the space. He shamelessly tries to call in another favor from Calder. It occurs to him almost as an afterthought that he never asked Virgil for money and that Virgil must have some squirrelled away somewhere if he is able to keep up on his medical bills and never have to worry. His exchange with Virgil illustrates Duddy’s cravenness and Virgil’s goodness. Virgil’s biggest concern is breaking his promise to Yvette. Realizing that Virgil never will, Duddy forges the checks.
In the last chapter, Duddy’s long-held dream has come to fruition. He has kept the promise he made himself—that he would own all the lakeside property. Though he never overtly promises his grandfather, Simcha, that he will own land, Duddy drives out to the property with his father, brother, and grandfather feeling assured that he has made Simcha proud and done as the patriarch wishes.
His behavior in these last scenes is consistent with who he’s been and how he’s behaved throughout the entirety of the novel. First he has a needlessly physical altercation with Dingleman, who has clearly arrived on the scene in an attempt to still seem menacing. Linda, another person who has wronged and devalued Duddy, is with him.
When Duddy sees Simcha walking away, returning to the car, all that he has built comes crashing down around him. Those he cares for most, especially his grandfather, see him for what he truly is—an egotist and a liar. Simcha’s disapproval wounds Duddy considerably, and Yvette deals the final blow. Duddy can’t walk into the restaurant and celebrate his success. He is, as he states, broke again, his life devoid of what matters most—friendship and love.
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