Pineapple Street

Pineapple Street is a satirical exploration of the lifestyles of the mega-wealthy of New York City. Using elements of the family drama to criticize how inherited wealth foments structures of exclusivity, Jackson explores the perspectives of three female protagonists at varying stages of their lives. She bookends these perspectives with the point of view of Curtis McCoy, a wealthy young man who handles his own inherited wealth morally and responsibly. Pineapple Street blends a coming-of-age family drama with romantic comedy to create a social commentary on the ways in which wealth can either influence or inhibit personal growth in contemporary America.

This guide refers to the version of Pineapple Street published by Penguin Random House in 2023.

Plot Summary

The wealth of the Stockton family has its origins in real estate development and politics and has been passed down and built upon over the course of many generations. Thus, the Stocktons are members of an elite class of New Yorkers who can afford absolutely anything they may want or need. Tilda and Chip, the mother and father of the family, are sticklers for tradition. Their oldest daughter, Darley, is married with children. Their youngest daughter, Georgiana, is a shy, sweet tennis player who works for a non-profit organization. Their son Cord has recently married Sasha, who is an outsider to the wealthy world of elite New Yorkers.

Sasha comes from a middle-class family and grew up in Rhode Island before marrying into the Stockton family through Cord. Despite her new official status as a member of the Stockton family, she senses immediately that her presence is not fully accepted by Cord’s family members. She and her new husband live in his childhood home, a massive, historic house on Pineapple Street, located in the exclusive neighborhood of Brooklyn Heights. This house represents the Stockton family’s legacy and lineage, but for Sasha, living there is as uncomfortable as living in a museum. Tilda and Chip still own the house and allow Sasha and Cord to live there for free, which is a significant privilege. Even so, Tilda has stipulated that everything in the house must remain the same, so Sasha must relinquish considerable autonomy in order to live there. Sasha appreciates that Cord is loyal to his family, but she notices that he never defends her, especially against his sisters, who behave coldly toward Sasha. (Because Sasha took offense when presented with the standard Stockton pre-nuptial agreement, Georgiana suspects that Sasha is only interested in Cord’s money. Darley is only suspicious of Sasha because she knows so little about her.) Despite these social setbacks, Sasha works hard to ingratiate herself with Cord’s sisters.

Darley is happily married to Malcolm, a Korean American man who grew up in a middle-class home like Sasha but earned his way into wealthier circles through his intelligence, hard work, and passion for aviation. He travels extensively for work but is utterly devoted to his family. Although Malcolm was willing to sign the pre-nuptial agreement, Darley who told him not to and let go of her inheritance. Her portion of the Stockton fortune will go instead to her children. Thus, Darley chose love over money, which emphasizes her priorities and values. The Stocktons readily accept Malcolm because, despite his status as an outsider, he makes enough money to keep up with the Stockton lifestyle. However, when Malcolm is unfairly fired from his job merely for being associated with a colleague who made a critical error, Darley is forced to reckon with her lack of income and inheritance. She is also forced to acknowledge that the racism and nepotism that pervades the society of the super-rich has irreparably damaged her husband’s career path.

Shy and easily embarrassed, Georgiana is the youngest Stockton child at 26 years old, but her overprotective family treats her as though she is much younger. Georgiana’s life is fun but lacks meaning. Although she works for a non-profit organization, she has no intentions of building her job into a larger career. She lives in an apartment that her parents pay for, and her life is mostly focused on playing tennis and partying with her friends. Essentially, Georgiana is aimless, but because of her wealth, she has no need to build a more productive life for herself. Georgiana also has a crush on an older, more powerful man at work named Brady, but she is too shy to approach him. When Brady makes the first move and they become a couple, Georgiana is elated. However, she soon discovers that Brady is married, and Georgiana chooses to continue their relationship, turning what she sees as true love into a tawdry affair. When Brady dies in a tragic plane crash, Georgiana is deeply saddened and develops a pattern of self-harm.

Darley and Georgiana keep their personal problems a secret from their family, but they both confide in Sasha, who sees this as an opportunity to build friendships with her sisters-in-law. However, when she finds out that they believe she is a “gold digger,” she realizes that they only shared their secrets with her because they don’t care enough about her opinion to fear her judgment. When the rest of the family finds out what Georgiana has been going through, they become angry with Sasha for not telling them. Sasha is placed in a lose-lose situation. When Sasha’s father becomes seriously ill, she returns to Providence to be with her family. This necessary distance between her and the Stocktons helps her to rethink her priorities and decide how best to proceed with her relationship with Cord. When she learns that she is pregnant, she knows that it is all the more urgent for Cord to start defending her from his family’s criticism. When Cord comes to Rhode Island to be with her, she confronts him with the sticky reality of their socio-economic class differences. Although the conversation makes Cord uncomfortable, it is a necessary confrontation to improve their relationship.

Meanwhile, Georgiana decides that she must become a better person. She is not sure how to improve herself, but she finally realizes that her current lifestyle is meaningless. She admires Curtis McCoy, a former high school peer who gave up his own family fortune by creating a foundation with his inheritance money. Georgiana is inspired by Curtis’s actions and decides to do the same. This decision shocks the Stockton family, but it also has the ripple effect of making all the Stocktons think more deeply about the influence of their privilege and the ways in which privilege can prevent them from recognizing the realities of the world.

Meanwhile, Darley meets a wealthy man named Cy Habib who has major connections with Emirates Airlines. He gets along well with Malcolm, who also has a passion for aviation. Through Cy, Malcolm lands a dream job with Emirates Airlines. Cord and Sasha give the house on Pineapple Street to Darley and her family, which fulfills one of Darley’s dreams. When Sasha hosts a birthday party for Chip, a fire starts in the house. Although the house is saved, many of the Stockton artifacts are destroyed. Thus, as the Stocktons change for the better, so too does the physical manifestation of their family’s history: the house on Pineapple Street.