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Jenny Jackson on her debut novel 'Pineapple Street'

Scott Simon

NPR's Scott Simon asks book editor Jenny Jackson about her debut novel, "Pineapple Street," set in the well-to-do Brooklyn Heights section of New York City.

Copyright © 2023 NPR. All rights reserved. Visit our website terms of use and permissions pages at www.npr.org for further information.

NPR transcripts are created on a rush deadline by an NPR contractor. This text may not be in its final form and may be updated or revised in the future. Accuracy and availability may vary. The authoritative record of NPR’s programming is the audio record.

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Book review: Pineapple Street is a witty debut about old money with a hasty ending

Pineapple Street By Jenny Jackson Fiction/Cornerstone/Paperback/342 pages/$25.92/Books Kinokuniya 3 stars

In the prelude of editor Jenny Jackson’s debut novel Pineapple Street, a character rushes out of a coffee house after uttering the line: “Oh, no! I left my Cartier bracelet in Lena’s BMW and she’s leaving soon for her grandmother’s house in Southampton!”

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book review: Pineapple Street by Jenny Jackson

Overview: The Stockton family has long called the fruit streets of Brooklyn home, and even as their children grew up and moved out, they stayed nearby. Pineapple Street  looks at a period in the wealthy family's life from three distinct perspectives. We experience the events of the story through youngest daughter, Georgiana, who's in her early twenties and the baby of the family, Darley, the oldest of the daughters, and Sasha, the brother's new wife who sees all the happenings of the Stockton's lavish lifestyle as a bewildered outsider. Overall: 5

Characters: 5 While we only have 3 point of view characters, all of the Stocktons get rich portraits drawn over the course of the book. Having these three different vantage points is also what makes the story so fascinating. It seems intentional and is impactful that Jackson chose to tell the story through the points of view of the three younger women in the family, and they do exhibit the most growth as the book progresses. 

Sasha always feels like the outsider. She grew up middle class in Rhode Island and often feels like she came from a different planet entirely than the Stockton household where each kid inherited tens of millions of dollars when their grandparents died and high society is their second language. She's the grounding force that puts into perspective the outlandish issues the family creates. Sasha also quickly bonds with Darley's husband Malcom as the only other outsider who doesn't understand the strange intricacies of their life. Sasha runs up against many pain points as she strives to find allies within the family as Darley and Georgiana are convinced that she's just a gold digger. As Sasha starts her new life with her husband, Cord, including moving into the Stockton's family home on Pineapple Street, she'll have to figure out how to claim her own space is a family devoted to keeping things the same.

Darley is a few years older than Sasha and has two kids. Much of Darley's story centers around her struggles as a stay at home mom questioning her loss of identity and income potential. The question of inheritance is also centered in Darley's story as she's chosen to forgo access to her trust and pass it directly to her children so that her husband, Malcom, didn't have to sign a prenup. Because she became a stay at home mom after her second child, though, that leaves her in the tough position of not having an income of her own. While Darley has grown up in her parents' New York society world, she still doesn't have an effortless experience navigating the politics of private elementary school and what happens when a seemingly steady single income vanishes overnight. 

Finally, Georgiana is in her early twenties and has never known a world beyond her privileged bubble. She lives in an apartment she bought with a down payment from her trust, she works a low paying job at a nonprofit with no regard for what her salary even is, and she's generally pretty self absorbed, something Sasha is always keen to point out. Being the youngest, Georgiana also follows the greatest evolution over the course of the novel. She meets a few people who make her seriously question her life trajectory and belief systems, looking beyond her tennis ranking for the most important things in life for the first time. Over the course of the novel, Georgiana questions everything she's ever known about her family and the world. 

Plot: 5 The multiple perspectives keeps the book moving as we get increased tension from knowing sides of the story that the other point of view characters we read about are oblivious too, so there's plenty of foreshadowing and extra painful miss communication. The tension and pacing are incredible, especially considering how slow and tedious some literary fiction books dealing with similar themes have been. This book is certainly looking for the line right between literary and commercial and does a beautiful job finding it. I have to wonder if this is owing to the fact that the author is an executive editor at Alfred A. Knopf. The book certainly has a sense of being aware of its readers need for drama and intrigue, and it's tightly plotted. Somehow, even in this wild family, there was only one point that felt like it pushed the details of the scene to a bit of an over the top place. 

Writing: 5 I couldn't put the book down from the very first page. The book hits the right notes of having a compelling plot and characters that you become quite invested in despite all of their flaws and lack of a connection to earth. At the end of the day, though, the book is truly about cutting through the noise to realize there are very few things that truly matter in the end, and family, even a dysfunctional one, is worth more than any divides that come between them from money, status, or perceptions.

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Jenny Jackson’s 'Pineapple Street' explores the changing landscape of New York’s mega-rich

Much of the buzz around Jenny Jackson’s debut novel, “Pineapple Street,” relates to the author’s impressive credentials as a book editor . In her years at Knopf, Jackson has established herself as a literary hit-maker for such authors as Cormac McCarthy, Gabrielle Zevin, Katherine Heiny and Emily St. John Mandel. This month, she released a book of her own.

“Pineapple Street” is the story of the old-money Stockton family, a carefully guarded clan of one-percenters living among the fruit streets of New York’s Brooklyn Heights neighborhood. Eldest daughter Darley traded her inheritance and her job in finance for motherhood. Sasha married into the family and struggles to fit in. And youngest daughter Georgiana gets entangled in an ill-advised relationship and tries to come to grips with what it means to be a trust-fund baby.

The novel reads like “Crazy Rich WASPs,” with characters uttering lines like, “Oh no, I left my Cartier tennis bracelet in Lena’s BMW, and she’s leaving for her grandmother’s house in Southampton!” The Stockton girls refer to their brother’s wife as “the Gold Digger,” and there’s lots of talk about real estate, private schools, party themes and tablescapes.

But Jackson deftly describes family dynamics — the secrets and passive-aggressive tactics that are so much a part of this social strata. She also explores the changing landscape of the mega-rich, including a younger generation of socialist-minded millennials who feel guilty about their wealth and want to give it away.

At its core, “Pineapple Street” is a contemporary novel of manners and relationships, a peek into how the upper crust lives. It’s a well-written family drama that would make an ideal summer read.

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Pineapple Street by Jenny Jackson

• Publication Date: March 12, 2024
• Genres: Fiction , Women's Fiction
• Paperback: 320 pages
• Publisher: Penguin Books
• ISBN-10: 0593490711
• ISBN-13: 9780593490716
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‘Pineapple Street’ Is ‘GMA’ Book Club Pick

BY Michael Schaub • March 6, 2023

Jenny Jackson’s Pineapple Street  is the latest pick for the Good Morning America book club.

Jackson’s debut novel, published Tuesday by Pamela Dorman/Viking, follows three women from a wealthy New York family. A critic for Kirkus called the book “a remarkably enjoyable visit with the annoying one percent, as close to crazy rich WASPs as WASPs can get.”

In a podcast interview with Kirkus’ Megan Labrise, Jackson said of her novel, “I really set out to write the exact novel that I most love to read. I’ve been a fan forever of Laurie Colwin; she’s one of my favorite all-time writers. And I love a lot of the writers that I’ve gotten to work with as an editor, Katherine Heiny and Jennifer Close and J. Courtney Sullivan and Helen Fielding and Kevin Kwan.”

Jackson shared the news of her book’s selection on Instagram, with a video of her watching the announcement on Good Morning America . “Literally screaming (and contemplating Pineapple-themed lower back tattoo),” she wrote.

Michael Schaub, a journalist and regular contributor to NPR, lives near Austin, Texas.

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Pineapple Street: A GMA Book Club Pick (A Novel) Hardcover – March 7, 2023

• Print length 320 pages
• Language English
• Publisher Pamela Dorman Books
• Publication date March 7, 2023
• Dimensions 6.25 x 1 x 9.25 inches
• ISBN-10 059349069X
• ISBN-13 978-0593490693
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• Publisher ‏ : ‎ Pamela Dorman Books (March 7, 2023)
• Language ‏ : ‎ English
• Hardcover ‏ : ‎ 320 pages
• ISBN-10 ‏ : ‎ 059349069X
• ISBN-13 ‏ : ‎ 978-0593490693
• Item Weight ‏ : ‎ 9.6 ounces
• Dimensions ‏ : ‎ 6.25 x 1 x 9.25 inches
• #369 in Family Life Fiction (Books)
• #611 in Women's Domestic Life Fiction
• #976 in Literary Fiction (Books)

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Jenny jackson.

Jenny Jackson is a vice president and executive editor at Alfred A. Knopf. A graduate of Williams College and the Columbia Publishing Course, Jenny lives in Brooklyn Heights with her family. Pineapple Street is her first novel.

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Pineapple Street

57 pages • 1 hour read

A modern alternative to SparkNotes and CliffsNotes, SuperSummary offers high-quality Study Guides with detailed chapter summaries and analysis of major themes, characters, and more.

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Chapters 5-9

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Summary and Study Guide

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.

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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.

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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.

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