A Successful Editor Turns Debut Author, Surprising Nearly Everyone

Jenny Jackson means onetime Brooklyn Heights resident Truman Capote no disrespect, and his quote “I live in Brooklyn. By choice” serves as an epigraph to “Pineapple Street,” her first novel. But Jackson sets off on a walking tour with a different Brooklyn Heights in her sights.

She gestures toward the red brick Heights Casino, where the novel’s old-money Brooklyn plays tennis year-round, and the St. George Hotel, which catered to Brooklyn’s rich of the Jazz Age. There’s the imposing bay-windowed house on Columbia Heights that inspired the heirloom-stuffed limestone at the heart of the book. And the Joe Coffee on the corner of Pineapple and Hicks streets is where Georgiana, the youngest daughter of “Pineapple Street”’s adamantly Social Register Stanton family, utters the immortal line, “Oh no, I left my Cartier tennis bracelet in Lena’s BMW and she’s leaving for her grandmother’s house in Southampton” as she is fatefully spotted by the reluctant heir to a zillion-dollar defense fortune.

Darley, Georgiana’s older sister, is a former finance crusher and increasingly reluctant stay-at-$10-million-home mom, while their mother, a ski-pole-thin event planner, has never met an issue of the Yale Alumni Magazine she didn’t scour for prospects for her unmarried daughter. Stuck, uncomfortably, in the middle, is Sasha, the middle-class New England girl who has married their brother, Cord, and, despite all signs to the contrary, is referred to as “the Gold Digger” by her sisters-in-law.

“It’s the novel Jane Austen would have written,” said the author Chris Bohjalian, “if Jane Austen lived in Brooklyn Heights in the 21st century.”

But Jane Austen didn’t hold a high-profile position in publishing, as well: Jackson, the author with a splashy debut on her hands, is also a vice-president and executive editor at Alfred A. Knopf. Bohjalian is one of her authors.

Jackson’s foray into writing came as a surprise to most who know her, not least those who have known her as editor, and raised questions: How will Jackson deploy her skills in her new circumstances? And what does it feel like to be on the other side of the author-publisher relationship?

The Essential Cormac McCarthy

‘Blood Meridian’ (1985). Loosely based on historical events, the novel follows a fictional 14-year-old referred to only as “the kid” as he drifts through the Southwest. “‘Blood Meridian’ makes it clear that all along Mr. McCarthy has asked us to witness evil not in order to understand it but to affirm its inexplicable reality,” Caryn James wrote in her review for The Times.

‘All the Pretty Horses’ (1992). This best-selling book is an adventure story about a Texan boy who rides off with his buddy to Mexico. “The magnetic attraction of Mr. McCarthy’s fiction comes first from the extraordinary quality of his prose,” Madison Smartt Bell wrote in his review.

‘The Crossing’ (1994). The novel begins on a small cattle ranch in New Mexico in the last years of the Depression and follows Billy Parham, a teenage cowboy as he repeatedly crosses the border with Mexico. “‘The Crossing’ is a miracle in prose, an American original,” Robert Hass wrote in his review.

‘No Country for Old Men’ (2005). This fast, violent story centers on a stone-cold killer, a small-town sheriff and an average Joe who stumbles across a leather case filled with more than $2 million. “‘No Country for Old Men’ is as bracing a variation on these noir orthodoxies as any fan of the genre could expect,” Walter Kirn wrote in his review.

‘The Road’ (2006). The book is a despairing account of a boy and his father lurching across the cold, wretched, corpse-strewn, ashen landscape of a post-apocalyptic world. “Mr. McCarthy has summoned his fiercest visions to invoke the devastation. He gives voice to the unspeakable in a terse cautionary tale that is too potent to be numbing,” Janet Maslin wrote in her review.

“It was like finding out your spouse is an Olympic equestrian,” said the author Kevin Kwan, who hit the publishing stratosphere with Jackson as his editor on “Crazy Rich Asians.” “Or better, given her natural skills, an Olympic gymnast.”

Since joining Vintage, Knopf’s paperback arm, in 2002, fresh out of Williams and the Columbia Publishing Course, and segueing to Knopf’s hardcover shop nine years after that, Jackson, 43, has established herself as a literary hitmaker with a track record of fostering best-selling authors who straddle the line between literary and commercial fiction, and nonfiction on occasion as well. With a vociferously loyal roster that ranges from such authors as Gabrielle Zevin and Emily St. John Mandel to Bohjalian, Peter Heller, Katherine Heiny, Jennifer Close, Esmeralda Santiago, Helen Ellis and the actress Selma Blair, she is also considered extraordinarily adept at helping market and promote her authors.

Zevin’s star-crossed gamers saga, “Tomorrow and Tomorrow and Tomorrow,” topped Amazon’s list of Best Books of 2022, ended up a Jimmy Fallon Book Club pick, and got a rare John Green recommendation. Almost the minute that Amazon’s Times Square billboard went up trumpeting the novel as its “#1” choice, Jackson shared it on her busy Instagram.

“She’s a complete star,” said the literary agent Amanda Urban, who, 10 years ago — on the advice of the late Sonny Mehta, Jackson’s boss and mentor — entrusted Cormac McCarthy and his long-gestating works in progress to a young Jackson. The two linked novels McCarthy delivered were heavy on esoteric mathematics, physics and intelligence theory.

“More than anyone around,” Urban said of Jackson, “she instinctively knew how to talk about these books.” “The Passenger,” published in October of last year, and “Stella Maris,” released in December, were greeted as a triumphant comeback for McCarthy.

Jackson said she was almost as surprised as the rest of the publishing world that she’d written a novel. Like countless others, she had felt isolated and unsettled as the pandemic “changed the world and the way we lived,” she said. Far from her normal epicenter among a younger cohort spanning a swath of publishing houses and literary agencies, Jackson wrote the novel, she said, in place of being able to talk and gossip and socialize with what had seemed to have become a vanished world.

For the first six months of the pandemic, she and her husband, Torrey Liddell — a partner at the production company Surreel Films — and their two young children lived with his parents at their country house in Sharon, Conn., not far from Hotchkiss, where both Liddell and his father had gone to boarding school. “I love Torrey’s family,” Jackson said, “but they’re not my family.” The complications of marrying into someone else’s family drive “Pineapple Street”’s fish-out-of-gene-pool plot.

The question around Viking and its Pamela Dorman imprint is whether the book, which comes out March 7 with an announced first printing of 50,000, could emerge as a “Sex and the City” that gets its sugar rush not at Magnolia Bakery but at Le French Tart on Henry Street where Jackson, blonde and thin and 5’3”, favors the almond croissants. Sold in a pre-emptive deal for a reported seven figures in April 2021, the novel is under option as a TV series by the production company PictureStart. Although Publishers Weekly called it “a clever if tepid debut,” Kirkus Reviews judged the novel a “remarkably enjoyable visit with the annoying one percent, as close to crazy rich WASPs as WASPs can get.”

Jackson wrote “Pineapple Street” in just four months after she read The New York Times article “The Rich Kids Who Want to Tear Down Capitalism,” about millennial one-percenters’ distinctly ambivalent relationship with the millions they stand to inherit. The conundrum visits the Stantons in “Pineapple Street” when Georgiana grows a social conscience and decides to give away her trust fund.

The book’s approaching launch has Park Avenue on high alert. The Colony Club and the Cosmo Club have asked about hosting events with Jackson. She said she remembers the first time she was invited to lunch at the Colony Club. Still an entry-level editorial assistant, she arrived wearing black jeans, “the nice J. Crew kind,” Jackson said with a laugh. Lunch had to be moved. She never made a mistake like that again.

More on Cormac McCarthy

This fall, the writer Cormac McCarthy returns with his first two novels since his 2006 book “The Road.”

“For someone who’s written a novel about class, I came to it surprisingly late,” said Jackson, who was raised in Ipswich, Mass., and attended a small progressive private school where teachers were called by their first names. She used to pass John Updike’s house there when she went for a run, she said. Now she is rereading his book “Couples” because she’s setting her next novel there.

In contrast, at Williams, where she studied poetry, she said she discovered that “there was a whole group of kids who took private planes for spring break.”

As a seasoned editor, Jackson has witnessed the eggshell egos and creative struggles of many of her authors, and has ridden the ups and downs of their insecurities and rough drafts. “Pineapple Street” had the potential of throwing the same emotional obstacle course her way.

J. Courtney Sullivan, whose first novel, “Commencement,” began her string of best sellers with Jackson, talked through some of those vulnerabilities with her, she said, and “how, as a writer, you have to put so much of yourself out there, and the risks that holds, the vulnerability.”

Jennifer Close, who has been with Jackson since they made “Girls in White Dresses” a best seller in 2011, exchanged texts with her almost daily. “The first time she got notes back for revisions,” Close said, “she texted me, ‘I hate revising. This is miserable. How do you not hate me?’ It was funny, because she’s a person her authors love.”

“I feel like I’ve always been sensitive to my authors,” Jackson said. “But it’s gone up a level. I’m never going to just dismiss a rude email one of them gets ever again.”

No one does fun like Jackson, her authors say, while keeping her editorial focus paper-cut sharp. She is a perpetual standout at the competitive game nights that Ellis holds as fund-raisers every year for One Story magazine. At the last gathering, Jackson dipped into the Truth or Dare bag for extra points and found herself drawing a Sharpie tattoo of a skull and cross bones on Bohjalian’s arm.

Jackson likes to joke that she “has the most boring résumé in publishing” because she hasn’t exactly moved around in her career. Zevin frames it differently, describing Jackson, and her trajectory, as a full-blown video game.

“A plucky adventurer,” Zevin wrote in an email, “let’s call her Jenny Jackson, because honestly, this is a very good video game character name! — travels through worlds to collect a series of tomes that, in combination, will unlock the secrets of civilization and maybe even save it!

“Her quest will take her from a post-apocalyptic landscape in the Midwest, to the elite world of the ultrarich in Singapore, and to many worlds in between. To collect the tomes, she must be highly observant, empathetic, and a master of language and transformation.

“In the final level, she reaches a world that is unexpected, but strangely familiar: It’s a world of her own devising.”

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