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Kaplan's Plot
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.
10 hr. 18 min.
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.
10 hr. 18 min.
320 pages, Hardcover
Published September 9, 2025
7 people are currently reading
5963 people want to read
About the author
Jason Diamond
22 books163 followersJason Diamond is a bestselling author, editor, speaker, and big eater. He was born in Skokie, Illinois just before Ronald Reagan took office, and remembers absolutely nothing about the Carter administration. He has lived in New York City for the bulk of his life and plans to die there, but he loves Chicago with all his heart. Jason has worked as a barista, server, fry cook, bookseller, and DJ. In 2008, he founded the site Vol. 1 Brooklyn and has curated hundreds of regular free literary events, including the popular 3-Minute Stories series.
He has written for The New York Times, New York Times Magazine, Outside, The Paris Review, The New Yorker, Esquire, Harper's Bazaar, Eater, The Wall Street Journal, New Republic, Bookforum, Tablet, Pitchfork, McSweeny's, NPR, and many other fine outlets.
His memoir, Searching For John Hughes (William Morrow/HarperCollins), was released in November 2016. His second book is The Sprawl. It was released by Coffee House Press in August of 2020. He is the co-author (with Nicolas Heller) of New York Nico's Guide to NYC, and in 2025, his debut novel, Kaplan’s Plot, will be released by Flatiron.
He has written for The New York Times, New York Times Magazine, Outside, The Paris Review, The New Yorker, Esquire, Harper's Bazaar, Eater, The Wall Street Journal, New Republic, Bookforum, Tablet, Pitchfork, McSweeny's, NPR, and many other fine outlets.
His memoir, Searching For John Hughes (William Morrow/HarperCollins), was released in November 2016. His second book is The Sprawl. It was released by Coffee House Press in August of 2020. He is the co-author (with Nicolas Heller) of New York Nico's Guide to NYC, and in 2025, his debut novel, Kaplan’s Plot, will be released by Flatiron.
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Displaying 1 - 15 of 15 reviews
June 30, 2025
What a fantastic book. It ticked all the right boxes: set in Chicago, old guess, gangsters, and high-tech bosses. Even a cameo mention of my hometown (Rockford). The book was engaging from the beginning. Loved it! Thank you Jason for this great book! Thank you NetGalley for allowing me an ARC copy.
August 23, 2025
What fun to listen to this audiobook about greater Chicago, set now and in the 1920s. Lots of famous and infamous cameos from Manny’s Deli and Maxwell Street to Mallort, the Sears/Willis Tower, and the city’s lack of a decent bagel place. (The author wisely stayed away from the very polarizing discussion about the best pizza.)
More than a trip down memory lane, this book tells the story of two young boys who flee the pogroms in Russia to make a life for themselves in America. It’s also a contemporary story about a dying woman (who happens to be a daughter of one of those two boys) and her son who grew up in the Chicago area and is visiting from San Francisco.
Family secrets, shame, and doing what one must are the main themes of this well narrated but occasionally slow book. My thanks to the author, publisher, @MacmillanAudio, and #NetGalley for early access to the audiobook of #KaplansPlot for review purposes. Publication date: 16 September 2025.
More than a trip down memory lane, this book tells the story of two young boys who flee the pogroms in Russia to make a life for themselves in America. It’s also a contemporary story about a dying woman (who happens to be a daughter of one of those two boys) and her son who grew up in the Chicago area and is visiting from San Francisco.
Family secrets, shame, and doing what one must are the main themes of this well narrated but occasionally slow book. My thanks to the author, publisher, @MacmillanAudio, and #NetGalley for early access to the audiobook of #KaplansPlot for review purposes. Publication date: 16 September 2025.
August 19, 2025
Rounded up from a 3.5
I expected this book to have a bit more excitement. In places where I was anxiously waiting for it to pick up, it somehow slowed down. What it lacked in thrills however it made up for in authenticity and heart. This book gave me an interesting lens to reflect upon my own family history through.
I expected this book to have a bit more excitement. In places where I was anxiously waiting for it to pick up, it somehow slowed down. What it lacked in thrills however it made up for in authenticity and heart. This book gave me an interesting lens to reflect upon my own family history through.
June 26, 2025
I won this advanced copy through the Goodreads Giveaways.
I give it 3.5 stars but rounded it up to 4 here. This is the story of a man who has returned to his childhood home in Chicago after the company he was one of the founders of in Silicon Valley failed due to criminal activities by his partners. Even though he didn’t necessarily partake, he knew the partners were likely not law abiding but he joined in anyway because he wanted the money, power and fame that it would bring him. It backfired.
He was not a very likeable man, Elijah. He returned to the home of his mother who was suffering from the late stages of cancer. His mother, Eve, had never been very warm and demonstrative mother. She was a famous poet and teacher. What ends up happening is Elijah finds a stack of letters addressed to his mother that she ignores and he investigates. This leads him to an old cemetery that has been in his family for nearly a hundred years but very few graves, one for someone he never heard of but carried the family name.
The book takes place in two timelines. Eve and Elijah in modern time and Yitz from the turn of the century until about 1960. Yitz is Eve’s father who was prominent in the Jewish mob and Eve had never shared the history with her son. So the book is Elijah learning from her and his own research about his family’s history and from Yitz’s point of view living it. The story brings the beginning of healing for Elijah and his mother and, also, for Elijah in the choices he made in his life.
It can be very violent and harsh, so there are some trigger warnings. But I feel like the author really was able to describe life for immigrants,notably Jewish immigrants, in the United States at the turn of the century for the 1900’s. Life was difficult, uncaring and violent. Right now, I feel as though not much has changed.
I do recommend this book. I was drawn into the story even though the characters were all unlikeable. Except, perhaps for Sol. It showed the criminal, dark side of Chicago that was prevalent then and , kind of, still is now.
I give it 3.5 stars but rounded it up to 4 here. This is the story of a man who has returned to his childhood home in Chicago after the company he was one of the founders of in Silicon Valley failed due to criminal activities by his partners. Even though he didn’t necessarily partake, he knew the partners were likely not law abiding but he joined in anyway because he wanted the money, power and fame that it would bring him. It backfired.
He was not a very likeable man, Elijah. He returned to the home of his mother who was suffering from the late stages of cancer. His mother, Eve, had never been very warm and demonstrative mother. She was a famous poet and teacher. What ends up happening is Elijah finds a stack of letters addressed to his mother that she ignores and he investigates. This leads him to an old cemetery that has been in his family for nearly a hundred years but very few graves, one for someone he never heard of but carried the family name.
The book takes place in two timelines. Eve and Elijah in modern time and Yitz from the turn of the century until about 1960. Yitz is Eve’s father who was prominent in the Jewish mob and Eve had never shared the history with her son. So the book is Elijah learning from her and his own research about his family’s history and from Yitz’s point of view living it. The story brings the beginning of healing for Elijah and his mother and, also, for Elijah in the choices he made in his life.
It can be very violent and harsh, so there are some trigger warnings. But I feel like the author really was able to describe life for immigrants,notably Jewish immigrants, in the United States at the turn of the century for the 1900’s. Life was difficult, uncaring and violent. Right now, I feel as though not much has changed.
I do recommend this book. I was drawn into the story even though the characters were all unlikeable. Except, perhaps for Sol. It showed the criminal, dark side of Chicago that was prevalent then and , kind of, still is now.
September 2, 2025
Those who love and know Chicago well will enjoy Kaplan’s Plot even more than I did - and I barely know Chicago, having visited it for the first time for a couple of days this summer.
Kaplan’s Plot explores the history of twentieth century Chicago, through a look at an immigrant Jewish family who escaped pogroms in Odessa. The two brothers couldn’t be more different in their approach to life in the US. Yitzhak “Yitz” becomes an important member of the Jewish mob, including lots of Prohibition activity, while running a “schvitz” (bath house) as a legitimate business front. His brother Sol becomes a kosher butcher. We meet them and a lot of other interesting characters through research that Elijah Mendes does in the present day - with the eventual assistance of his mother Eve (nee Kaplan). Elijah is in Chicago after his career as a “tech bro” in the Bay Area flamed out. He’s living with his mother who has advanced cancer. While there he finds, among all the mail she has been ignoring, letters from a rabbi at the local Hebrew Benevolent Society, asking about a cemetery the family apparently owns - which was total news to Elijah. The story bounces between the present day and the experiences of the Kaplan brothers over the years, including run-ins with other underworld groups in the city, including those run by the Italians and the Irish. And don’t miss White Jimmy (who is black)!
Chicagoland fans will recognize many famous landmarks including the Sears/Willis Tower, Manny’s Deli, Maxwell Street and more, including a description of the now-famous Chicago-style hot dog (no ketchup!!). The Jewish rep was lovely. I had to smile at how Elijah always had to say, “No, I’m not adopted”, because of the widespread incorrect assumption that all Jews have exclusively European heritage. Elijah’s heritage includes a Jewish father whose family stems from Egypt and Morocco.
I found the going a bit slow, but still enjoyable. Family secrets, shame at how Yitz had to make a living, and the mystery of the “plot” in the title, along with the concept of intergenerational trauma, pervade the narrative. I bounced between the print edition and the audiobook which was beautifully narrated by Neil Hellegers and Alex Knox.
Thank you to Flatiron Books for the opportunity to read an advance reader copy of this book and to Macmillan Audio and NetGalley for the opportunity to listen to an advance copy of this audiobook. All opinions are my own.
Kaplan’s Plot explores the history of twentieth century Chicago, through a look at an immigrant Jewish family who escaped pogroms in Odessa. The two brothers couldn’t be more different in their approach to life in the US. Yitzhak “Yitz” becomes an important member of the Jewish mob, including lots of Prohibition activity, while running a “schvitz” (bath house) as a legitimate business front. His brother Sol becomes a kosher butcher. We meet them and a lot of other interesting characters through research that Elijah Mendes does in the present day - with the eventual assistance of his mother Eve (nee Kaplan). Elijah is in Chicago after his career as a “tech bro” in the Bay Area flamed out. He’s living with his mother who has advanced cancer. While there he finds, among all the mail she has been ignoring, letters from a rabbi at the local Hebrew Benevolent Society, asking about a cemetery the family apparently owns - which was total news to Elijah. The story bounces between the present day and the experiences of the Kaplan brothers over the years, including run-ins with other underworld groups in the city, including those run by the Italians and the Irish. And don’t miss White Jimmy (who is black)!
Chicagoland fans will recognize many famous landmarks including the Sears/Willis Tower, Manny’s Deli, Maxwell Street and more, including a description of the now-famous Chicago-style hot dog (no ketchup!!). The Jewish rep was lovely. I had to smile at how Elijah always had to say, “No, I’m not adopted”, because of the widespread incorrect assumption that all Jews have exclusively European heritage. Elijah’s heritage includes a Jewish father whose family stems from Egypt and Morocco.
I found the going a bit slow, but still enjoyable. Family secrets, shame at how Yitz had to make a living, and the mystery of the “plot” in the title, along with the concept of intergenerational trauma, pervade the narrative. I bounced between the print edition and the audiobook which was beautifully narrated by Neil Hellegers and Alex Knox.
Thank you to Flatiron Books for the opportunity to read an advance reader copy of this book and to Macmillan Audio and NetGalley for the opportunity to listen to an advance copy of this audiobook. All opinions are my own.
August 28, 2025
A fantastic book on the city of Chicago and the crime families that ruled it for decades. This book doesn’t follow the Irish and Italians gangsters we commonly see, but the Jewish ones, recently arrived from the pogroms of Russia, Ukraine, Poland et al. and ready to scramble and fight for every inch in the Windy City. We follow two brothers who slipped out of Odessa in the middle of the night and plucked down without family or connection other than their heritage. Over the decades, we see the brothers diverge as one becomes a successful butcher like his father in Ukraine, while the other begins a slow ascent up the ladder in organized crime.
This story is uncovered in bits and pieces as Elijah, a descendent of the brothers, comes from home after failing in the Bay Area to help his mother through her late-stage cancer. If any of the book is not needed, it’s the discussions about Elijah’s fall from grace from a WeWork-like hostel-like startup. But that could simply be my absolute disinterest in talks of start-ups and tech. The mother-son interactions though are often very winning and Eva is typically the most humorous part of the story. (I also appreciated the throwaway line featuring an alt-history version of her becoming more famous due to a Lithub-style Joan Didion tote)
As secrets emerge and graves are uncovered, we accelerate to a shocking conclusion that mixes history and present day.
This story is uncovered in bits and pieces as Elijah, a descendent of the brothers, comes from home after failing in the Bay Area to help his mother through her late-stage cancer. If any of the book is not needed, it’s the discussions about Elijah’s fall from grace from a WeWork-like hostel-like startup. But that could simply be my absolute disinterest in talks of start-ups and tech. The mother-son interactions though are often very winning and Eva is typically the most humorous part of the story. (I also appreciated the throwaway line featuring an alt-history version of her becoming more famous due to a Lithub-style Joan Didion tote)
As secrets emerge and graves are uncovered, we accelerate to a shocking conclusion that mixes history and present day.
August 8, 2025
This was another book that I was fortunate enough to win in a goodreads giveaway. I thought that the story that took place was very good. It is a dual timeline story that starts out in modern day and peeks back into the past of before 1910 and goes into the 1920's. Not only are the characters wonderful but the storyline is as well. There are some cery informative events that are talked about before and during the first world war. I will admit that I was hooked by this story at the very beginning!
In the modern timeline we are introduced to Elijah who has returned to Chicago after his business has failed. He has also returned to help take care of his mothef Eve who is in the late stages of cancer. They have never had the best relationship but they are willing to tolerate each other. While goibg through some of his mothers things he finds some old letters which leads him to the family cemetery filled with secrets.
In the historical timeline we are taken back to 1909 and introduced to Yitz who happens to be Eve's father. Yitz is a Jewish immigrant who has recently arrived to America. Shortly after his arrival he becomes involved with the Jewish mob becoming a very prominent figure.
In the modern timeline we are introduced to Elijah who has returned to Chicago after his business has failed. He has also returned to help take care of his mothef Eve who is in the late stages of cancer. They have never had the best relationship but they are willing to tolerate each other. While goibg through some of his mothers things he finds some old letters which leads him to the family cemetery filled with secrets.
In the historical timeline we are taken back to 1909 and introduced to Yitz who happens to be Eve's father. Yitz is a Jewish immigrant who has recently arrived to America. Shortly after his arrival he becomes involved with the Jewish mob becoming a very prominent figure.
August 14, 2025
This review is for the audio version, narrated by Alex Knox and Neil Hellegers (both were wonderful).
This was a decent read.
Elijah has moved home to be with his mother after her cancer diagnosis and his startup failure. While there they start bonding in a way they never have and he begins to learn the complicated history of his very complex family, specifically his grandfather "the businessman", Yitz.
I wasn't sure how much I was going to like this going in, but this was written so well that I was quickly pulled into the story.
It touched on so many things that we all deal with, family relationships that aren't perfect, hating people we love, and forgiving them for the wrongs that they cause us.
The character work here was, for me, outstanding. Elijah clearly had some growing up to do, and he needed someone to push him into it, and Eve, his mother was a great catalyst for that. Yitz was a difficult man to like, but you couldn't deny cheering him on as things were getting dirty on the streets of Chicago in the 20s and 30s.
The plot, while a bit slow, was a good slow. It moved at a good pace to relay the story in a way that felt like it conveyed the proper gravity. The pacing felt *good*.
This was definitely worth the time to read.
This was a decent read.
Elijah has moved home to be with his mother after her cancer diagnosis and his startup failure. While there they start bonding in a way they never have and he begins to learn the complicated history of his very complex family, specifically his grandfather "the businessman", Yitz.
I wasn't sure how much I was going to like this going in, but this was written so well that I was quickly pulled into the story.
It touched on so many things that we all deal with, family relationships that aren't perfect, hating people we love, and forgiving them for the wrongs that they cause us.
The character work here was, for me, outstanding. Elijah clearly had some growing up to do, and he needed someone to push him into it, and Eve, his mother was a great catalyst for that. Yitz was a difficult man to like, but you couldn't deny cheering him on as things were getting dirty on the streets of Chicago in the 20s and 30s.
The plot, while a bit slow, was a good slow. It moved at a good pace to relay the story in a way that felt like it conveyed the proper gravity. The pacing felt *good*.
This was definitely worth the time to read.
August 19, 2025
I won an ARC of this book through a Goodreads giveaway. Dual timeline set in Chicago. Present day, Elijah has returned home to stay with his mother, Eve, who is dying of cancer. In going through her mail, he finds a letter from a rabbi asking Eve to contact him. Elijah goes to see the rabbi and learns not only about a relative unknown to him but also about property owned by his family worth a lot of money. Elijah decides he wants to learn about his family’s past.
Late 1800s, Yitz and his brother Sol leave their home as children to board a boat to America. They end up in Chicago, hooked up with a Jewish gang. From there, we watch Yitz’s rise up the gang ranks, along with the trail of bodies he leaves behind.
I enjoyed Yitz’s story. Not because I liked Yitz - he had his moments, but he was pretty ruthless overall - but there was a lot going on in his story. I felt Elijah’s story dragged quite a bit and didn’t have much point to it.
The ending of the book attempted to rip my heart out though, and that last little twist in the end??? Oh, that made me mad!
3.5 ⭐️, but I do want to note that, I hope an editor goes through this before the final copies are released!!
Late 1800s, Yitz and his brother Sol leave their home as children to board a boat to America. They end up in Chicago, hooked up with a Jewish gang. From there, we watch Yitz’s rise up the gang ranks, along with the trail of bodies he leaves behind.
I enjoyed Yitz’s story. Not because I liked Yitz - he had his moments, but he was pretty ruthless overall - but there was a lot going on in his story. I felt Elijah’s story dragged quite a bit and didn’t have much point to it.
The ending of the book attempted to rip my heart out though, and that last little twist in the end??? Oh, that made me mad!
3.5 ⭐️, but I do want to note that, I hope an editor goes through this before the final copies are released!!
September 8, 2025
I wasn't sure about this book. It's not science fiction or fantasy. The setting is urban. The synopsis mentions an American "underworld," which means there's a mob element to it. (I tend to get bored with mob/gang/ club, etc stories.) Basically, a lot of things about this book are on my not really interested to read about list. Perhaps the mystery of the grave plot and the element of a family secret drew me in. By the end, I didn't feel like the book wasted my time, and I'm always pretty impressed with books well outside my usual bookish zone of interest that capture my attention, especially if they do it like this one did.
My thanks to Macmillan Audio for the ALC, for which I willingly give my own, honest opinion.
See the full review on my blog:
Blog / Instagram / BookBub
My thanks to Macmillan Audio for the ALC, for which I willingly give my own, honest opinion.
See the full review on my blog:
Blog / Instagram / BookBub
July 12, 2025
When Elijah thinks he's hit rock bottom and returns to Chicago to regroup and help his dying mother he learns to put his here in now into perspective via the past. His family, specifically his Grandfather was a Gangster boss and his family has suffered and gained from his criminality, as has the community then and now. Elijah learns to view his own life choices and relationships via the inherited traumas of the past and sets to right the past as he forgets a better relationship with his mother and those around them. Well written, darkly tragic and comedic.
This entire review has been hidden because of spoilers.
September 6, 2025
Hard to believe this is a debut novel. Very well written. Great story that speaks to Jewish history, depression, generational trauma. 4.5 stars. Thank you to Goodreads, the author, and publisher for the free print copy:-)
July 9, 2025
Got a free copy for review from the publisher. I was surprised how beautiful and moving this book was considering it was about gangsters and intergenerational Jewish trauma.
August 2, 2025
3.5 stars
September 8, 2025
Such a surprise to be moved by a book about gangsters. It's also about generational trauma and family, and those things come through the deeper you get into this book.
Displaying 1 - 15 of 15 reviews