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60 pages 2 hours read

Jenny Jackson

Pineapple Street

Fiction | Novel | Adult | Published in 2023

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Character Analysis

Sasha Stockton

Sasha Stockton is one of the central protagonists of the novel. She is an artist who works for herself as a successful graphic designer. Sasha grew up in a loving middle-class family in Rhode Island. She is now married to Cord Stockton and therefore has entered a new world of socio-economic class expectations, enormous wealth, and tight-lipped, tight-knit communities. Sasha is seen as an outsider and therefore contributes an important narrative perspective to the many issues that the novel addresses. Her perspective allows Jackson to insert important social criticism of the myopic privilege represented by the Stockton family.

When Sasha is first introduced, she struggles to ingratiate herself into the Stockton family. Though Tilda and Chip treat her kindly, there is a distinct distance between them. Part of this distance is what Sasha identifies as the Stockton family’s inability to talk about vulnerable topics. Sasha has a more difficult time connecting with Darley and Georgiana, who are suspicious of Sasha and call her a “gold digger” behind her back. Sasha makes headway with Darley first, who confides in Sasha, and later develops a tenuous connection with Georgiana as well. Darley’s decision to confide in Sasha brings the two women closer together and helps them to develop a friendship, whereas Georgiana’s confiding in Sasha makes Georgiana even more wary of Sasha. Ultimately, Sasha comes to terms with her outsider status. She grows frustrated with Cord, who doesn’t defend her from the criticism of his family. This dynamic precipitates a change in their relationship. Because of a toxic former relationship with her high school boyfriend, Sasha doesn’t want Cord to be obsessively affectionate with her, but she worries that he’s more loyal to the Stocktons than he is to her. Sasha’s pregnancy also escalates the tension of divided loyalties because she needs to be able to rely on Cord no matter what situation they find themselves in. Sasha makes Cord understand her by confronting the role that issues of class and wealth play in their relationship. In doing so, she reclaims her autonomy and advocates for herself. She also demonstrates that the integrity of their relationship is more important than money.

Georgiana Stockton

Georgiana Stockton is the youngest Stockton sibling. She is another central protagonist in this novel. Georgiana has long been spoiled by her family’s wealth and their desire to protect her as the baby of the family. Georgiana works for a non-profit organization that consults on healthcare infrastructure in needy communities, but this job is not a career for Georgiana. Because of her extreme wealth, Georgiana doesn’t need to develop a career. The expectations for Georgiana are that she will marry someone from her tiny social circle and have children. Georgiana is not encouraged to explore a career or grow beyond her childish routines of playing tennis and partying. She is characterized as shy and vulnerable by her family, and this characterization enables her to flit around, living a shallow life that has little meaning, thus emphasizing the importance of Achieving Meaning Through Agency.

Georgiana’s life changes for the worse when she falls in love with a coworker named Brady. Brady is older than Georgiana and higher up in the organization, which increases Georgiana’s sense of intimidation. When Brady makes the first move and initiates a relationship, Georgiana feels true happiness. However, this happiness is quickly complicated by the discovery that Brady is married. Despite this betrayal, Georgiana continues the relationship. Though the relationship must be kept a secret, Georgiana believes she is happy. This demonstrates that Georgiana is highly influenced by other people.

When Brady dies in a tragic and unexpected plane crash, Georgiana cannot mourn him publicly because their relationship was a secret. She also cannot rely upon her family and friends for support because she is ashamed of her own role in the affair, and her family and friends are all averse to dealing with conflict. Thus, Georgiana turns against herself. She becomes consumed by her grief and anger and mixes alcohol with prescription drugs, spending days at a time alone in her apartment. This breaking point forces Georgiana to take a closer look at her life, which she realizes is meaningless. She aspires to be more like Curtis, who turns his incredibly large family fortune into a philanthropic foundation. Georgiana’s resulting decision to divest herself of her family fortune is admirable and necessary to her character development. She takes a huge risk in becoming a philanthropist, but this risk helps her to achieve agency and meaning in her life.

Darley Stockton

Darley is an important protagonist in the novel. She is the oldest Stockton sister and is very connected to her family. Darley has a different relationship with money than might be expected from someone with such a financially wealthy legacy. Darley doesn’t believe that she is entitled to money. As a stay-at-home mom, she worries that the fortune that had been spent on her education led to nothing. Darley gave up her lucrative and thrilling career for her children, and she still misses the feeling of going to work. Darley’s lifestyle is consistent with the Stocktons, but she forfeited her inheritance when she married Malcolm because she didn’t want him to sign the pre-nuptial agreement. Malcolm makes enough money to keep up with the Stocktons’ lifestyle, so Darley isn’t challenged to really think about money until Malcolm is unjustly fired from his prestigious position. Confronted by the unexpected issue of his unemployment, she must reckon with the reality of money as a source of security.

Darley is characterized through kindness and loyalty. Although she, like Georgiana, is wary of Sasha, she welcomes Sasha into the family and develops a real friendship with her. Darley is fiercely loyal to her family, which for her also includes Malcolm and his loving parents. Darley’s character is developed through the external conflict of Malcolm getting fired, which makes her rethink her privilege and realize how racism and legacy play a major role in keeping people from connecting with each other. Darley seeks to break that cycle, enabling a more loving, compassionate, and open Stockton family legacy.

Cord Stockton

Cord Stockton is Sasha’s husband and the only Stockton son. He is charming, kind, and smart. Though he benefits greatly from his family’s wealth, he doesn’t come across as snobbish or even wealthy. One of the things that differentiates Curtis from the rest of his family is his willingness to meet people outside of the mega-wealthy bubble. He is not afraid, like Darley is, of people taking advantage of him. Curtis has a natural affinity for seeing the world around him as interesting and exciting, not as a threat to his family legacy and to his privilege. Despite these positive qualities, however, Cord has internalized his family’s avoidance of conflict, so even though Sasha’s class difference doesn’t bother him, he refuses to engage with how it bothers other people. He is also fiercely loyal to his family and must eventually come to realize that in being too defensive of his family, he has unwittingly ostracized Sasha. Cord ultimately learns to put Sasha first, and they become the first Stocktons to move out of Brooklyn Heights, forging a new path and a new legacy.

Curtis McCoy

Curtis McCoy is a secondary character who influences Georgiana’s character development. The novel’s Prologue and Epilogue are told through his perspective, which bookends the major developments that occur in the novel. Curtis is of the Stocktons’ world. His father owns an arms dealership that has generated the family hundreds of millions of dollars. But unlike Georgiana, Curtis is acutely aware of his privilege and the absurdity of his wealth. He criticizes Georgiana for having fun at the “Oligarch Chic” party because he analyzes how he and his wealthy peers have often been reductive in their thinking of the world around them. Rather than simply criticize and chastise others, however, Curtis puts his money where his mouth is. He sets up a foundation to donate his immense inherited fortune to various charities. This places Curtis in the role of modeling moral behavior and inspiring Georgiana to do the same. By the end of the novel, he and Georgiana are dating, which is foreshadowed in the prologue and is an excellent fit because both Curtis and Georgiana know where they’ve come from and are headed in the same philosophical direction.

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