Jenny Jackson’s debut novel, “Pineapple Street,” offers readers a delicious glimpse into the rarefied world of Brooklyn Heights’ old money families. Set in the “fruit streets” of one of New York’s most exclusive neighborhoods, the novel follows the Stockton family—a dynasty ensconced in limestone mansions and private clubs—as they navigate love, class divides, and the growing pains of self-awareness. With wit and precision, Jackson (who works as a vice president and executive editor at Alfred A. Knopf) delivers a compelling examination of wealth and its discontents that manages to be both critical and compassionate.
The novel’s strength lies in its three central female characters: sisters Darley and Georgiana Stockton, and Darley’s sister-in-law Sasha. Through their alternating perspectives, we gain entry into a world of unexamined privilege, where family dinners involve “tablescape” competitions and casual references to Palm Tree Islands in Dubai can expose one’s lack of geopolitical knowledge.
Intersecting Lives: The Stockton Women
Jackson’s novel revolves around three women at different stages of confronting their relationship with wealth and privilege:
- Darley Stockton Kim, the eldest daughter, who gave up her trust fund to marry Malcolm, a Korean-American banker she met in business school. Darley’s decision to forego a prenup meant losing access to her inheritance, a choice she only comes to question when Malcolm loses his job at Deutsche Bank due to a colleague’s indiscretion. Her story highlights the vulnerability that can come with traditional gender roles, as she finds herself financially dependent on her husband after quitting her career to raise their children.
- Sasha Rossi Stockton, who married Darley’s brother Cord and moved into the family’s limestone mansion on Pineapple Street. Coming from a middle-class Rhode Island background, Sasha struggles to fit in with the Stockton family’s conventions and their thinly-veiled disdain for outsiders. Discovering that Darley and Georgiana refer to her as “the Gold Digger” behind her back only compounds her feelings of alienation.
- Georgiana Stockton, the youngest sibling, whose journey through grief and self-discovery provides the novel’s emotional core. After falling in love with Brady, a married colleague who dies in a plane crash, Georgiana begins questioning the purpose of her inherited wealth and contemplates giving it all away.
Class Consciousness and Wealth Disparity
Jackson deftly navigates the complex territory of class in America, exposing the often unspoken divisions that shape our social interactions. What makes “Pineapple Street” particularly insightful is how it reveals the ways wealth protects and insulates its possessors:
- The ability to avoid discomfort: The Stocktons only discuss pleasant topics at dinner, avoiding any mention of global inequality or suffering.
- The insularity of social circles: Darley reflects on how the wealthy tend to socialize with other wealthy people because “their friends could all keep up, they could all pay their way, there was no awkwardness about offering to cover shares or lend a tux or waiting until a paycheck cleared on a Friday.”
- The inherent suspicion of outsiders: The fear that others are using them for their connections, their weekend homes, or their influence permeates the Stocktons’ interactions with non-elites.
When Sasha confronts Cord about class differences, she acknowledges a difficult truth: “I probably did like it that you were rich. I feel like a terrible person saying that… But I didn’t know what it would actually mean for our lives. I didn’t know that I’d always feel like an intruder.”
The Weight of Inheritance
One of the book’s most compelling themes is how inherited wealth shapes identity and purpose. Georgiana’s crisis following Brady’s death leads her to question what it means to possess millions while others struggle to meet basic needs. Her desire to give away her fortune—approximately $37 million—horrifies her family, who view such wealth as protection against life’s uncertainties.
Jackson skillfully portrays the invisible lessons wealth imparts to its heirs. As Georgiana realizes during therapy sessions:
“Unbeknownst to her, she had been trained her entire life to protect her wealth. They had tax advisers and investment advisers, they made careful end-of-year adjustments to offset losses, and while they could enjoy the fruits of their labor (or the fruits of their ancestors’ labor) they were raised with the holy understanding that they must never, ever touch the principal.”
Prose That Sparkles with Wit
Jackson’s writing is crisp and observant, filled with sharp one-liners and astute social commentary. The prose moves briskly, delivering both humor and insight in equal measure. Consider this description of the Stockton parents’ social life:
“Chip and Tilda decided to throw a housewarming party at their new apartment on Orange Street and asked that their children and spouses arrive early. It was on a Wednesday evening, because most of their friends spent their weekends at country homes and some liked to go up Thursday night. The Stockton parents’ social life in the city existed only between Monday and Wednesday, before their friends scattered to the far reaches of Long Island and Litchfield County.”
Or this exchange between Sasha and her mother-in-law about maternity basics:
“Oh! We have the bassinet from when you all were babies!” Tilda jumped up and strode out of the parlor. She came back three minutes later carrying a wicker Moses basket. The canework looked sharp and it smelled slightly weird. “All three of you slept in this,” she said fondly.
“That’s amazing,” Cord said, his eyes glistening.
“Do you think that’s mold?” Sasha asked, inspecting a slightly green crust on the bottom. Everyone ignored her.
The Novel’s Shortcomings
Despite its many strengths, “Pineapple Street” occasionally stumbles in its execution:
- Character development is uneven: While Georgiana’s emotional journey feels authentic and compelling, Darley’s character sometimes lacks depth, and Sasha can feel like a device primarily designed to expose the Stocktons’ classism.
- Convenient resolutions: Some of the novel’s conflicts wrap up too neatly, particularly Malcolm’s employment situation, which resolves with a deus ex machina job offer that feels slightly improbable.
- Structural issues: The three-part narrative structure sometimes loses momentum, particularly in the middle sections where the women’s stories unfold separately with limited intersection.
- Missing perspectives: We never get the viewpoints of Cord or Malcolm, which would have added valuable dimensions to the family dynamics and gender politics at play.
Comparisons and Context
“Pineapple Street” joins a growing canon of fiction examining wealth, privilege, and class divides in America. Readers who enjoyed Cynthia D’Aprix Sweeney’s “The Nest” or Cristina Alger’s “The Darlings” will find familiar territory here, though Jackson’s focus on old money rather than new gives the novel a distinctive flavor.
The book also has echoes of Curtis Sittenfeld’s “Prep” in its attention to social codes and class markers, though with adult protagonists instead of adolescents. Like Edith Wharton before her, Jackson excels at depicting a society bound by invisible but rigid rules, where knowing which fork to use or which club to join signals belonging.
As a debut novel, “Pineapple Street” showcases Jackson’s considerable talents as a social observer and witty chronicler of upper-class foibles. Her publishing background undoubtedly informs her literary sensibilities, resulting in a polished first effort that balances entertainment with meaningful social commentary.
Final Verdict: A Sparkling Debut
“Pineapple Street” succeeds as both social satire and emotional journey. Jackson has crafted a novel that entertains while prompting readers to examine their own relationships with money, privilege, and family loyalty.
The book’s greatest accomplishment may be how it humanizes its wealthy characters without excusing their blind spots. We see the Stocktons’ flaws clearly—their snobbery, their reflexive protectiveness of wealth, their casual dismissal of outsiders—but we also witness their growth as they confront these limitations.
By the novel’s end, the Pineapple Street house has literally and metaphorically burned, making way for new beginnings. In the delightful epilogue, told through a Christmas card and viewed through the eyes of Georgiana’s new boyfriend Curtis (a fellow wealthy heir intent on dismantling his own fortune), we see that the Stockton family has evolved while maintaining its essential character.
For readers looking for a smart, entertaining novel about family dynamics among the privileged set, “Pineapple Street” delivers a satisfying blend of social insight and storytelling pleasure. Jackson has announced herself as a writer to watch, with a keen eye for the nuances of class and the complications of love across socioeconomic divides.
