Pineapple Street

In the first chapters of Pineapple Street, Jackson establishes certain characteristics that define members of the very-wealthy upper-class echelons that dominate New York City. A popular expression states, “Money talks, wealth whispers,” and this is an apt expression to describe the lifestyle of the Stocktons. For example, Cord’s very lack of an outward appearance of wealth indicates that he is comfortable enough with his extreme wealth that he feels no need to flaunt it. It never occurs to him to show off his money because, like his sisters, he grew up with other equally wealthy people, so there was no one to compete with. Another notable aspect of wealth that “whispers” is the reality that those who inherit their wealth do not have to work to earn money, and therefore, there is no need to show off the possession of wealth that one never had to earn directly. It is important to note that all of these reasons for being quietly wealthy are subconscious; Cord does not speak openly about his money or how he chooses to style himself in relation to it because immense wealth is simply part of the backdrop of his life—it is scenery, and therefore unworthy of comment.

Despite this natural reticence when it comes to displaying evidence of one’s money openly, the Stocktons’ immense wealth is clearly established at the outset of the novel. Chip and Tilda hold several expensive properties in one of the most expensive cities in the world and are so well-off that they can easily sign over their million-dollar townhouse to Cord and Stockton without selling it. Similarly, they can afford to attend the most expensive schools and country clubs without concern. Their disposable income is so enormous that most people have no practical way to conceptualize this amount of wealth. In the epigraph preceding the Prelude to the novel, Jenny Jackson quotes Zoe Berry of The New York Times as stating, “Millennials will be the recipients of the largest generational shift of assets in American history—the Great Wealth Transfer, as finance types call it. Tens of trillions of dollars are expected to pass between generations in just the next decade.” This epigraph is an important foundational concept for understanding the history and unspoken psychology governing the dynamics of the Stockton family. Jackson purposefully creates these characters to be unrelatable to all but the tiny percentage of people who benefit directly from the Great Wealth Transfer.

Inherited wealth is therefore a crucial part of Jackson’s characterizations of the Stockton family; for Cord, Darley, and Georgiana, there is a guaranteed source of income for the rest of their lives. This extreme privilege powerfully impacts how they navigate and understand (or fail to understand) the world around them. For example, Georgiana can easily take a job at a not-for-profit health infrastructure development organization because a low salary is of no concern to her. Even Darley, who gave up her trust fund to preserve the integrity of her marriage, has the safety net of wealthy family members. Darley may have given up her own access to the family’s wealth, but her children will receive that wealth in her stead, thereby ensuring that whatever she does with her own life, her children are guaranteed to have access to immense wealth when they come of age. Furthermore, Darley gave up her right to the family money knowing that her husband would still be capable of earning a large salary. Therefore, Darley has in no way relinquished her privileged lifestyle even though her inheritance is no longer an immediate factor in her finances. Another important example of the far-reaching effects of inheritance can be found in the dynamics of Cord’s job. Cord works for his father at the family real estate company, which positions him to become the inheritor not just of family wealth, but of the family’s entire real estate legacy.

Another important aspect of inheritance is embodied in the Brooklyn townhouse on Pineapple Street, for the house symbolizes the overwhelming influence of the tight-knit Stockton family and the power of the legacy they have created. The inside of the house is a living testimonial to the Stockton children and the family legacy. Because Chip and Tilda have left their children’s belongings in the house as though the teenage versions of Darley, Cord, and Georgiana are still in residence, this pattern implies their deep attachment to preserving memories of the past and maintaining consistency as the years progress. In a larger, more practical sense, families like the Stocktons tend to resist change in financial realms as well, for sudden, ill-considered decisions might threaten the long-term security of their legacy. The house thus becomes a physical relic of this larger philosophical mindset, for just as Tilda and Chip refuse to relinquish control of the items in the house, they also maintain control of their many financial and emotional assets—and by extension, of the other members of the family who are tied to those assets. Faced with the sheer weight of such tradition and power, Sasha must learn to navigate her awkward position as an untrusted outsider to this highly exclusive enclave. In the eyes of the elder Stocktons, her innocent desire to improve the house implies that she also wants to criticize and change the family itself, and therefore she is seen as something of a threat to the Stockton legacy. Thus, the house is both a practical setting for the events of the novel and a powerful symbol of the elder Stocktons’ attachment to the grandeur of their legacy and their ongoing resistance to Sasha as a middle-class outsider.

In a novel that explores the lives of the ridiculously wealthy, it is necessary to include an outsider who is in a position to challenge the status quo developed through living within the bubble of privilege, and this is seen throughout the literary legacy that inspired the creation of Jackson’s novel. For example, in E. M. Forster’s Howards End (1910), Leonard and Jacky Bast are two characters who struggle with their financial status and lives because of the whims and attitudes of the rich. In D. H. Lawrence’s Lady Chatterley’s Lover (1928), everything that Lady Chatterley knows about her financial security and privileged lifestyle is upended when she falls in love with Oliver Mellors, a groundskeeper. These are but two examples in the long literary tradition that critiques the lifestyles and mindsets of the privileged few. Thus, Sasha’s role as an outsider is foreshadowed to be one that will challenge the Stockton family’s status quo, ultimately forcing them to reevaluate their standards and become better versions of themselves. It is also important to note that the ostracization that Sasha experiences is not entirely intentional, for they are an extremely close-knit family who all live near one another and do nearly everything together. Sasha may be married to Cord, but spending time with his family, who are all on such familiar terms with one another, makes her feel as though she is encroaching on a realm that she is not meant to share. Sasha is also an outsider because of her middle-class background, which influences how she interacts with people who are as wealthy as the Stocktons. The stark class difference is immediately established in the novel and foreshadows an important source of tension that introduces the theme of Navigating Class Relations.