Pineapple Street is an ode to Brooklyn and a cursory commentary on our times
- Mallory
- Nov 23, 2023
- 4 min read
Pineapple Street, Jenny Jackson
Pamela Dorman Books, March 7, 2023 315 pages

I liked this book; I didn't love it and I probably wouldn't recommend it to friends. But if you have read it, I'd be thrilled to talk about it with you!
The prose was strong - good, clear writing. While the characters were decent enough, I wished for more engagement between them. The book's purpose is to shed light on intergenerational wealth and its contribution to our society's demise. This purpose I wholeheartedly support, but it takes much too long to for us to get to the nitty gritty of this issue and even when we do, it's glossed over hurriedly without fully imagining the fall out. We just stop once we get there and we aren't really thrust into any true conversations about generational differences, the shrinking middle class, the 1% versus 99% and all the societal woes that result from these differences. Thus, it feels like Jackson has just touched the tip of the iceberg and didn't give us the fun of exploring all of it which is disappointing. The result is a basic novel that had so much opportunity to do more.
SPOILERS AHEAD
We start the novel with Curtis McCoy but we don't know who he is yet or his intrical part to this story. By the time he is reintroduced I had actually forgot about him. This is saying something, becuase I read this book rather quickly over the course of 3 or 4 days. Unfortunately we lose the importance of this character and his service as the catalyst towards change because he is just skimmed over and relegated to the fringe. Curtis is so much more important than the other characters we are forced to dwell on. Georgiana, instead of wasting her time with a married man (Brady) who has lots of morals to save the world but not enough to remain faithful to his wife, should be paired up with Curtis earlier on in the novel so that we can break into her need to give away her trust fund. Doing so would allow for much more (entertaining) conflict among the family and a more engaging story about generational differences - parents and children, boomers and millenials. Instead we are left with too much emphasis on tennis and the beautiful neighborhood that is Brooklyn.
Georgiana's emphasis on helping Pakistan (inspired by Brady) made me cringe. This is not that I have any misgivings about helping young girls in Pakistan. Far from it. But it is just another demonstration of a rich white girl with absolutely no adversity assisting a random country to which she has no ties and women's health because why, it sounds nice? Why couldn't we have had some sort of exploration into various non profits she could have been paired up with, some right in New York City? The high-priced tuition of the Henry Street School her neice and nephew attend likely needed a boost in diversity. Perhaps she could have started with a small scholarship program there. It would have been 1) close to her as a person, 2) more to the point - increasing diversity and equity among classes, and 3) given some sort of purpose to Darley who was quite two dimensional despite being the most level headed of the Stockton children. Again, missed opportunity.
My last point is a bit more personal to me. I'm from Rhode Island and was excited that Sasha was too until I realized that Jackson has no idea about the RI landscape and its demographics. She misrepresents its residents. What suburb to Providence is beachy?????? Hint: there isn't one. The beaches are to the south on both sides of the bay. Why not just name the town as you go out of your way to mention Newport as the boat slip for Sasha's brother's girlfriend? If Sasha is from Newport, it would make much more sense for the storyline that Cord and Sasha met on a trip of his and his family's from New York to Newport - a frequent vacation spot for city dwellers that harkens back to the gilded age of summer "cottages" for Vanderbilts and Astors and would have been a perfect play on the generational wealth concept. It would also highlight the class system concept Jackson presents that Sasha is not from means. As we learn more about Sasha, in a final chapter no less, she's actually not poor at all and not from any sort of disadvantaged family - she was able to get herself to NYC for college afterall even if her brothers are trashy boneheads. Both parents are still together, alive and mostly healthy, and not trashy at all and because we are given that judgment early on, it becomes a bit offensive. Jackson could have selected Prudence Island, Bristol, Warren, or Warwick as their hometown to make the genuine impact she was seeking for the type of family Sasha hailed from and what it meant to her outlook in life without the cheesy disdain and "gold digger" label. Due to my close relationship with lil Rhody, I was distracted every time we interacted with Sasha's family always thinking in the background that they couldn't possibly be living in a beachy suburb of Providence. In this way, Jackson's debut misses the mark again and is honestly a bit insulting because Sasha's family really could have taught the Stockton's a thing or two.
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