Walking the Brooklyn Heights That Inspired “Pineapple Street” Author Jenny Jackson

The esteemed editor turned writer discusses her debut novel, a sharp comedy full of observations about wealth and inheritance, on a stroll through the fictional story’s real-life backdrop.
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"Nothing captures your imagination quite like the idea of a house full of secrets," book editor and author Jenny Jackson says to me as we walk through New York’s sought-after Brooklyn Heights neighborhood among its famously well-preserved townhouses. Most are low-rise charmers built before the Civil War, presumably full of their own equally well-preserved secrets.

Jackson is about to release her debut novel, Pineapple Street (out Tuesday), which begins when graphic designer Sasha and her new husband, Cord Stockton, move into his childhood home in the Brooklyn Heights Historic District, lent to the couple by his extremely well-to-do parents. Sasha’s from a firmly middle-class family in Rhode Island; Cord is from enormous wealth—think patchy sweaters, weekend house in the Hamptons. The especially tight-knight Stockton family built their wealth from real estate development, particularly along the Brooklyn waterfront. Cord’s parents and two sisters have moved out of the huge-and-not-just-New-York-huge mansion on the fruit street abutting Brooklyn Bridge Park, but their genteel furniture and knickknacks have not. They’ve left antique lamps, plush curtains, and boatloads of nautical-style decor. Jackson writes: "Sometimes Sasha found herself wandering the house in the evenings, running her hand along the ancient frames and candlesticks, whispering ‘Batten down the hatches’ and ‘Swab the deck,’ making herself laugh."

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The novel takes a sharp shot at the WASP interior aesthetic endemic to Brooklyn Heights, where Jackson has resided—quite happily—for almost a decade. "I’ve been deliriously in love with this neighborhood from the jump," she tells me as we gaze up at her old apartment, a buttercream-yellow brick building on the real-life Pineapple Street (naturally). Jackson, her husband, and their two children have since moved to another Brooklyn Heights address, but Pineapple Street is still her favorite. "Everyone was like, ‘Oh my god, that’s the cutest address ever!’" she says. "I’ve never gotten such a reaction. There’s something a little magic about it."

Pineapple Street has all the delectable charm of its namesake road. But Jackson uses the Stockton mansion as the home base for the book’s examination of thorny topics related to the wealthy Brooklyn enclave and others like it—namely, the ethics of inherited wealth, the contours of envy, and the dynamics of social aspiration. The novel is less of a sumptuous portrait of a palatial mansion and more of a cultural critique that employs a mansion as a symbol. The house comes to the couple attached with a thousand invisible strings: Sasha can’t change the curtains, she can’t move an old clock. The Stocktons’ generosity is twinned to control.  

"The aesthetic of Pineapple Street in this book is at odds with the aesthetic of [much of] New York City," says Jackson. "So often, when you go inside these homes, you don’t feel like you’re in New York. It feels like Connecticut or another century." The author points to an enormous dog wagging its tail down the block, one of many we’ve passed on our walk. "It’s very WASP-y to have a big dog," she says. "It speaks to the size of the apartments that are hidden back in here. It’s like the ultimate flex." A man walks by us with two large dogs—I watch him until he’s around the corner, creepily hoping I’d see which manse he approaches.

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Beyond its depiction of WASP-y Brooklyn aesthetics, Pineapple Street also dissects the tensions between the Stockton siblings who span generations and have differing attitudes about wealth. The older sister, Darley, believes that family wealth is something you keep building for the next generation. The younger, right-out-of-Brown sister, Georgiana, oscillates between luscious entitlement and Marxist critique. In one scene, she scrolls through dating profiles for young men that read things like "Searching for a Commie Mommy" or "Never eat anything with a face. Except the rich." Georgiana, an excellent brat in the manner of Amy from Little Women, doesn’t seem to consider she might be the rich they’d like to eat. Shortly after, she runs off in a hurry saying, "Oh no! I left my Cartier bracelet in Lena’s BMW!"

"I’m an older, geriatric millennial, like on the cusp of Gen X," Jackson says. "I was raised with this really simplistic attitude toward money. I loved Troop Beverly Hills and Clueless and MTV Cribs. I was like, ‘Oh, money, I want to make some of that stuff.’ People a decade younger than me have grown up with a much more sophisticated view on inherited wealth than I ever had."

Perhaps Pineapple Street’s most deftly drawn dynamic is the unease of moving into a home already surging with history. As we walk past the neighborhood’s well-known Moonstruck house (currently occupied by Amy Schumer), Jackson mentions briefly living with her husband and children at her in-laws’ Connecticut home for the first few months of the pandemic. "Living in your own family's detritus is really different than living with your in-laws’ detritus," she says. "You know, [there were] these weird sculptures my husband made at summer camp when he was a kid, [and a] lamp made of cork that had a weird smell to it." 

Much like the book’s main character, Jackson found that when you’re living in someone else’s house, the combination of total unfamiliarity and incredible intimacy can be dizzying. A house full of secrets is only fun when you know that you’ll learn them.

Top photo by Alexander Spatari / Getty Images.

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