Kaplan's Plot: A Novel

by Jason Diamond

Overview

Notes From Your Bookseller

Buried secrets. Healing. Reflection. When his business fails, Elijah returns home where past and present collide and a riveting family mystery unravels. Delving into generational trauma and Chicago’s dark history, this is a suspenseful and haunting read.

One of the most anticipated books of the year by the Chicago Review of Books, Debutiful, The Millions, Hey Alma, and the Orange County Register

“A gangster novel of epic scale.” —People

“A sprawling, funny, Jewish family saga. . . . Kaplan's Plot concerns Chicago, cemeteries, secrets and crimes, and the enormous gift of loving somebody for who they truly, imperfectly are.” —Boston Globe

Elijah Mendes was hoping for a more triumphant return to Chicago. His mother, Eve, is dying of cancer, his business flamed out, and he has nowhere else to go. So he returns to Chicago feeling listless and shattered, worried about how he’s going to help his mother despite their chilly relationship. He finds some inspiration when he discovers that their family owns a Jewish cemetery and that a man he’s never heard of, his great-uncle Solomon Kaplan, is buried in a plot there. With a new sense of purpose—and an excuse to talk more deeply with his mother—Elijah begins pursuing a family mystery of extraordinary proportions.

Elijah discovers his grandfather Yitz, Eve’s father, was a powerful gangster in the 1920s. She was ashamed and never spoke about him to Elijah. As secrets unravel, the past and present become intertwined, and Yitz’s story forces Elijah and Eve to bond in ways they never have before and begin to accept each other, not as who they wish they were but as they both are.

Kaplan’s Plot is an astonishing balancing act between the ruthless and the tender, the superficial and the truth, by a writer with tremendous promise.

Product Details

ISBN-13:	9781250385918
Publisher:	Flatiron Books
Publication date:	09/09/2025
Pages:	320
Product dimensions:	6.20(w) x 9.30(h) x 1.20(d)

About the Author

Jason Diamond is the author of Searching for John Hughes and The Sprawl. His work has been published by the New York Times, Vulture, Esquire, GQ, and many other outlets. He writes the Substack The Melt on old, new, and evolving classics. He was born in Skokie, Illinois, and currently lives in Brooklyn with his family. Kaplan’s Plot is his first novel.

Editorial Reviews

One of the most anticipated books of the year by the Chicago Review of Books, Debutiful, The Millions, Hey Alma, and the Orange County Register

“A gangster novel of epic scale.”—People

“The book, by turns comic and sharp, bends history toward story until it feels both familiar and strange.” —The Forward

“Readers who love a sprawling, funny, Jewish family saga should check out Kaplan’s Plot [. . .] concerns Chicago, cemeteries, secrets and crimes, and the enormous gift of loving somebody for who they truly, imperfectly are.”—Boston Globe

“Jason Diamond is a genius.” —Hey Alma

“In Jason Diamond’s excellent Kaplan’s Plot, we meet Elijah Mendes, a man who’d pursued the modern American Dream (getting rich off dubious tech) only to see it fizzle out as his business goes under. Returning to Chicago, he’s met with a family mystery he feels compelled to unravel, along the way getting to know his family history, his mother, his city, and ultimately, himself. This delicious novel is a love letter to Chicago, and a testament to the possibility of generational healing.” —Lindsay Hunter, author of Hot Springs Drive

“A dazzling fictional debut, Jason Diamond’s Kaplan’s Plot calls to mind both John Irving’s darkly funny tales of family dysfunction and E. L. Doctorow’s evocative dives into the early 20th century American underworld. At the same, Diamond sneaks in deeper truths about family history, generational trauma and a quintessentially Midwestern sense of Jewish identity.” —Megan Abbott, NYT bestselling writer of The Turnout

“In this wild multigenerational ride from Odesa to Chicago to Hollywood, Jason Diamond whisks us through shootouts, numbers games, and the countless visible and invisible turning points that shape a life. A meditation on guilt and inheritance wrapped in a page-turning crime story, Kaplan’s Plot will shock, move, and entertain you all at once.” —Anna North, New York Times bestselling author of Outlawed

“Kaplan’s Plot is something magical—an original, beautifully written and deeply humane novel that is also a page-turner with a powerful ending.” —Adelle Waldman, bestselling author of Help Wanted

“A rich tapestry of a Chicago Jewish family [. . .] Diamond crafts an affecting portrait of the bond mother and son gradually form over revelations about the past [. . .] A memorable tale of the American dream gone sideways.” —Publishers Weekly

“Diamond’s debut novel is a stunning story of how families bend to accommodate the unspoken, and how, every once in a while, a tenacious individual might straighten things out. ” —The Millions

“Sweeping . . . a journey of discovery about intergenerational trauma, the ripple effects of state and personal violence, coping mechanisms across time and space, and the ties that bind us to the past even as we barrel into the future. Elijah, his mother, and his grandfather are unforgettable, and their story is all-consuming. Readers will adore this trip to Chicago’s present and vivid past.” —Booklist

From the Publisher

2025-07-04
Having flamed out at a California startup, Elijah Mendes returns home broke to be with his cancer-stricken mother in Chicago, where he uncovers dark secrets about his Jewish family.

His mother, Eve, an acclaimed poet working on her memoir, has avoided learning about the criminal activities of her Russian-born father, Yitzhak “Yitz” Kaplan. But Elijah’s research reveals he was the murderous head of a Jewish Maxwell Street mob. In alternating chapters, the novel traces Yitz’s rise from errand boy for head mobster Avi Kaminsky to the equally ruthless killer who deposes him. Yitz’s more-reserved younger brother, Solomon, is happiest running his classy butcher shop, but his place in infamy was secured when as a boy he saved Yitz from an attacker by lethally shoving a wooden stick into the assailant’s neck. The women in the story, including Eve’s ill-fated mother, do not have a happy time of it. Elijah, whose late lawyer father “was a Hispanic Jew or Moroccan or something,” ultimately finds connections between his (Elijah’s) empty existence and that of his grandfather, whose corpse “continued the lonely existence that the man who once inhabited the body experienced every moment of his life.” First-time novelist Diamond does a solid job of tracing the rise and fall of the Jewish mob in Chicago, highlighting their dealings with the Irish (who didn’t learn “to respect the Jews”) and the Italians (enemies with “flair and style”). You can’t go wrong with characters named Izzy the Trout and Jerry Knish. It’s too bad Elijah is such a bland protagonist and that the novel contains so few surprises or revelations—though Elijah’s dis of Hyde Park may qualify as one for certain readers.

An ambitious novel with a better backstory than contemporary one.

Kirkus Reviews

2025 Barnes and Noble Best New Books of the Year, Long-listed