‘Pineapple Street’ By Jenny Jackson Review: A Breezy Book With Big Bank Accounts

In Jenny Jackson’s novel Pineapple Street, the WASP-y Stockton family lives on the “fruit streets” — Pineapple, Cranberry and Orange — of Brooklyn. They make tablescapes and play tennis, they donate and they behave badly.

After reading Jackson’s most recent, highly consumable work, touted as a “delicious Gilded Age family drama”, we had questions. Can inherited wealth ever be moral? Did the novel do enough skewering? Should it have done more skewering?

Spoilers ahead.

Emma Gleason, commercial editor: An easy read, I churned through this page-turner on a rainy Sunday. While this isn’t a ruthless evisceration of wealth and class — we get plenty of that in the news right now — Jenny Jackson comes at the one-percenters from a different angle, and it’s an enjoyable book. Its breeziness was clever, I think, capturing that effortlessness and ease that the economically privileged have.

Dan Ahwa, fashion and creative director: It also highlighted their painful lack of awareness — the casual racism niche communities in NYC face on a daily basis, the prejudice, the bizarre eccentricities and unspoken rules that can only exist in a world built up through generational wealth.

EG: Beyond the trimmings of luxury, wealth and whether it’s deserved or not, is the main theme of the book. Explicitly so, with an epigraph at the beginning, about the impending intergenerational wealth transfer, quoting from The New York Times — which, coincidentally published an excellent investigation about the topic this May, a good companion read, as is the recent deep dive from Curbed, a New York magazine verticle, into the eyewatering cost of actually living in New York City’s most coveted neighbourhoods. Topical stuff!

DA: Very topical. This book’s timely release coincides with shows like White Lotus and Succession, and films like Triangle of Sadness which are fuelling an appetite for a certain ‘wealth porn’ and this desire to give the one per cent their comeuppance.

There’s a lot of discussion at the moment around inequality, and the book is adding to this narrative by prompting this inquiry, not necessarily about how wealth is achieved, but what is done — when you have this type of wealth — to help those less fortunate than you.

EG: Do you think Jackson lands the message? Is she harsh enough?

DA: I think part of a book like this is to also offer up a satirical kind of entertainment without going too deep. She’s given us an overview in terms of messaging, but I think it’s only scratching the surface.

EG: An interesting throughline was the symbols of class, and how these are upheld and protected. “Every society had traditions, institutional knowledge, their own innate sense of how things should be done,” writes Jackson.

These are the things I find particularly fascinating about the wealthy, like the unspoken rules and aesthetic signaling of New York society — do they show the fallacy of the American Dream, or do they provide the framework for people to try to climb and assail?

DA: Can anyone honestly say in 2023 that the American Dream is alive and well?

There’s definitely an undertone of critique here around this idealistic concept and Jackson does it purely through her observations. Malcolm’s experience alone deserves some credit as it’s something any migrant family will experience, especially in America. Achieving this idea of an American Dream as a child of migrant parents requires you to experience some pretty ugly behaviour in the pursuit of such a dream — that’s a concept any WASP won’t be able to fully understand.

EG: Just as much as wealth, perhaps even more so, this book is about family: dynamics, characters, cliques, pretenders, loyalty and exclusivity. I love reading books about families, the more generations the better!

DA: It’s universal too. It reminded me a little of Crazy, Rich, Asians by Kevin Kwan (who also offered a one-line review on the book’s cover funnily enough: ‘smart and deliciously fun’). Whether it’s NYC or Singapore, those familial relationships and how they are tested because of money matters make for eternally good fodder. Jackson gives it to us in the type of gossipy manner people in these circles would be familiar with at a dinner party or charity event, which made reading this book even more fun.

EG: No one is particularly likable. Although there were no big baddies either (it could have done with a human villain, other than capitalism and the trust system).

What did you think of the characters? Matriarch and tablescape queen Tilda Stockton reminded me of Bunny MacDougal (Charlotte York’s mother-in-law).

JG: I can definitely see Blair! Actually, even Serena van der Woodsen. Floating from one space to the next with cascading locks and a fraught vision of what she wants out of life, and who she wants to be.

EG: Some of the characters are grappling with whether they’re good people. They voted Democratic, they gave to Planned Parenthood, they had museum memberships. Their families sat on boards, they paid for tables at benefits, they tipped generously.

“Her own parents had even paid for both of Berta’s kids to go to college,” thinks Georgiana, the youngest sibling, who is flirting with radical charity. Was the inclusion of White Saviourism meant to be critical? It wasn’t explicit enough to me. I couldn’t tell how the author felt about non-profits and altruism.

DA: There’s definitely the desire to want to be good, but the family wealth seems to hang over them and test their everyday relationships and decision-making to the point where they all become a little insufferable.

Even her subtle description of the white women in Georgiana’s non-profit organisation returning to the office from India wearing saris with clogs was a very brief example of a complex cycle. It says a lot about how people like to ensure their superiority is intact when it comes to their philanthropic efforts. Just enough help, but not enough that they become self-sufficient. This is the fine line people walk around performative do-gooding, when in fact deep down inside, they’re actually being despicable.

EG: Can inherited wealth ever be moral? It’s a question the book ramps up at the end, as the plot examines the family’s trusts and assets more closely — including how the rich secure, consolidate (and hide) their wealth.

“Tax advisers and investment advisers, they made careful end-of-year adjustments to offset losses, and while they could enjoy the fruits of their labour (or the fruits of their ancestors’ labour) they were raised with the holy understanding that they must never, ever touch the principal. Intertwined with this doctrine was the fact that marrying outside their class would dilute their wealth. It was best for the rich to marry the rich.”

If you want to read about a truly tragic downfall for an elite family, I recommend reading The Magnificent Ambersons, a very ahead-of-its-time book by Booth Tarkington, published in 1918. If it’s darkly satirical wealth porn and the horrors of fame and materialism you’re after, pick up 1998′s Glamorama by Bret Easton Ellis.

DA: The Magnificent Ambersons is a hot tip. Glamorama is such an extravagant read, which I really enjoyed. The entire book is sickeningly good.

Another great on-theme consideration is Frederic Morton’s book The Rothschilds: A Family Portrait, about the most powerful banking family in the world. It’s a little dorky non-fiction, but much like the Medicis, it’s a really great historical look at how one of the most powerful families in history attained and maintained their wealth.

JG: Little Fires Everywhere, by Celeste Ng, would also make a nice follow-on. It’s less decadent but is similarly about rules in a perfectly manicured neighbourhood, about what’s right and wrong, while being an excellent character portrait. It also has the added drama of arson.

What did you think of Pineapple Street’s ending?

EG: I did want more payoff at the end. Everyone kind of landed on their feet or learnt a lesson — which felt very television — and no one really had any consequences, or was that the point?

DA: Very American, right? I think someone should have died lol.

JG: Who wasn’t philanderer Brady.

DA: Someone give this to the BBC to adapt for a European drama with a more fatal ending, please.

Pineapple Street by Jenny Jackson (Hutchinson Heinemann, $37) is out now.

Previously in the Viva Book Club: Everything we thought while reading Paris Hilton’s memoir