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Pineapple Street


Pineapple Street

PINEAPPLE STREET, a smart first novel from publishing executive Jenny Jackson, takes readers into the exclusive world of the one-percent through the lives of one wealthy family living in Brooklyn Heights.

The Stocktons are a living example of generational wealth in America today. Tilda and Chip raised their family in a gilded limestone on Pineapple Street, one of the many “fruit streets” in their Brooklyn neighborhood. Eldest daughter Darley is married to a banker named Malcolm. When they wed, she declined her trust fund (thereby foregoing the standard prenup that each Stockton spouse is expected to sign) in favor of letting her husband be the breadwinner for their family of four.

"PINEAPPLE STREET is an engaging and absorbing read, with a supremely satisfying conclusion, perfect for book groups or to pass along to a good friend."

Darley’s brother, Cord, works for their father’s real estate investment firm. His wife, Sasha, is the most unlike the rest of the family in more ways than one. She was raised solidly middle class in a seaport town in Rhode Island and has never felt fully accepted into Cord’s family, especially among his sisters. She and Malcolm have a tenuous bond, being the two outsiders, and silently mouth “NMF” (“not my family”) to each other when one of the Stocktons makes a clueless comment about trust funds or flying private. Georgiana is the youngest of the Stockton brood at 26. She has never really thought about their enormous wealth until she suffers a great loss.

The Stockton children never had to worry about money or their financial futures. But when Malcolm is fired from his prestigious banking job --- a secret that Darley keeps from her family --- she starts questioning her decision to turn down her trust fund when they married: “She thought about her own prenup for the millionth time. Maybe she had made a stupid mistake when she gave up her trust, sure. But her biggest mistake had been giving money so much power over her life. By keeping Malcolm’s secret she was buying into the idea that her world was a club only available to those with a seven-figure income.”

Cord and Sasha have moved into the family’s home on Pineapple Street when Tilda and Chip decided to “downsize” to a smaller yet stately apartment on nearby Orange Street. As grateful as Sasha is to her in-laws, the palatial mansion feels a bit staid and outdated for her tastes. She tries to make the place a home for them, but her mother-in-law dissuades her whenever she attempts any alterations: “The more Sasha thought about it, the angrier she felt. She was stuck in a lose-lose situation, a member of a family in which she had no voice, she had no vote, where doors were closed and envelopes remained sealed and money was a string that tied them all together and kept them bound and gagged.” Sasha feels even more distanced from the Stocktons when she overhears Darley and Georgiana call her a “gold digger” at a family wedding. She’s had enough.

Georgiana divides her twenty-something time between her job at a local non-profit and her family’s private tennis club. When she begins an ill-advised affair with a married coworker, she begins to question not only her own morals but also her place in the world. An impromptu meeting with school friend Curtis McCoy, a wealthy nepo baby who wants to rid himself of his family’s fortune (gained through military manufacturing), rattles Georgiana to her core. He informs her, “Income inequality is the most shameful issue of our time. I’m worried that my kids will look back and see a country that completely abandoned morality, that let people die of hunger while the wealthy took tax breaks.” Georgiana has an epiphany: “It was the money that made her so horrible. It had made her coddled and spoiled and ruined, and she had no idea what to do about it.”

Jenny Jackson’s deft debut takes on the topic of generational wealth with a keen Austenian eye, but she refrains from harshly judging her characters. She leaves it up to her readers to make up their own minds. As an inhabitant of Brooklyn Heights herself, Jackson lives among families like the Stocktons, making her a perceptive observer of their kind. PINEAPPLE STREET is an engaging and absorbing read, with a supremely satisfying conclusion, perfect for book groups or to pass along to a good friend.

Reviewed by Bronwyn Miller on April 6, 2023

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