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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.
11 pages, Audiobook
Published September 16, 2025
78 people are currently reading
7131 people want to read
About the author
Jason Diamond
23 books177 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 - 30 of 66 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 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.
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.
October 17, 2025
4.75/5 rounded up
I received an ARC of the audiobook.
I typically don’t ready literary fiction, but I’m glad I gave this a chance. I went in blind, and found myself engrossed in familial secrets, generational trauma, and mob bosses in the heart of Chicago. There are rich layers to both timelines that kept me engaged.
My only complaints are: following both timelines was tricky with an audiobook since they did jump around a bit, and some of the earlier chapters are quite lengthy.
I received an ARC of the audiobook.
I typically don’t ready literary fiction, but I’m glad I gave this a chance. I went in blind, and found myself engrossed in familial secrets, generational trauma, and mob bosses in the heart of Chicago. There are rich layers to both timelines that kept me engaged.
My only complaints are: following both timelines was tricky with an audiobook since they did jump around a bit, and some of the earlier chapters are quite lengthy.
October 27, 2025
Book Review: Kaplan’s Plot by Jason Diamond
Kaplan’s Plot is a story of Chicago, organized crime, and a family saga spanning from the 1920s to the present day.
Elijah is caring for his mother, who is suffering from cancer, when he discovers his family’s connection to a building in Chicago. As he digs deeper into his family’s past, he learns that his long-dead grandfather wasn’t just a “businessman,” but an immigrant deeply entrenched in Chicago’s organized crime during the 1920s. As Elijah decides how to navigate his family’s past, he must also confront his relationship with his poet mother and his own personal and professional failures.
The story is also told through the POV of Yitz, who came to Chicago as a child from war-torn Odessa in the early part of the twentieth century. He quickly falls in with the Jewish mob and rises through the ranks due to his ruthlessness and street smarts.
I really enjoyed the world-building and mythology surrounding Chicago during Prohibition and its ties to organized crime. It was difficult to root for Yitz, who I found to be a terrible human being, but it was satisfying to see his grandson Elijah evolve as the story progressed. Overall, this was an engaging and well-told piece of fiction that explores the darker parts of family legacies.
Rating: ⭐️⭐️⭐️⭐️
Narrator Notes: Kaplan’s Plot is read by Neil Hellegers and Alex Knox, who do an excellent job voicing these two men—related by blood but living in separate centuries.
Disclosure: An advance audio copy was provided by Macmillan Audio for review purposes.
Kaplan’s Plot is a story of Chicago, organized crime, and a family saga spanning from the 1920s to the present day.
Elijah is caring for his mother, who is suffering from cancer, when he discovers his family’s connection to a building in Chicago. As he digs deeper into his family’s past, he learns that his long-dead grandfather wasn’t just a “businessman,” but an immigrant deeply entrenched in Chicago’s organized crime during the 1920s. As Elijah decides how to navigate his family’s past, he must also confront his relationship with his poet mother and his own personal and professional failures.
The story is also told through the POV of Yitz, who came to Chicago as a child from war-torn Odessa in the early part of the twentieth century. He quickly falls in with the Jewish mob and rises through the ranks due to his ruthlessness and street smarts.
I really enjoyed the world-building and mythology surrounding Chicago during Prohibition and its ties to organized crime. It was difficult to root for Yitz, who I found to be a terrible human being, but it was satisfying to see his grandson Elijah evolve as the story progressed. Overall, this was an engaging and well-told piece of fiction that explores the darker parts of family legacies.
Rating: ⭐️⭐️⭐️⭐️
Narrator Notes: Kaplan’s Plot is read by Neil Hellegers and Alex Knox, who do an excellent job voicing these two men—related by blood but living in separate centuries.
Disclosure: An advance audio copy was provided by Macmillan Audio for review purposes.
January 16, 2026
I really enjoyed much of this book. The book follows two separate narrative plots – in the current day, Elijah Mendes is a failed tech god who after losing his business and barely avoiding jail has limped home to Chicago to take care of his dying Jewish mother; while there he stumbles on a family mystery about a long-ago burial. Diamond uses that as his entrée to the world of Elijah’s grandfather Yitz, a who came to Chicago from Eastern Europe as a poor Jewish orphan and clawed his way to the top of the criminal underworld.
Diamond really does a good job of laying out the two very different worlds – both narrative threads held my interest, and it was quite fun to see how he ultimately brought them together. The main plot twists were not surprising, but nonetheless packed an emotional punch. The parts focused on the Jewish immigrant experience really resonated with me – Diamond is excellent at painting a nostalgic but clear eyed picture of the world that was. The resolution seemed a little too easy, but overall a satisfying read
Rating – 4 stars
Diamond really does a good job of laying out the two very different worlds – both narrative threads held my interest, and it was quite fun to see how he ultimately brought them together. The main plot twists were not surprising, but nonetheless packed an emotional punch. The parts focused on the Jewish immigrant experience really resonated with me – Diamond is excellent at painting a nostalgic but clear eyed picture of the world that was. The resolution seemed a little too easy, but overall a satisfying read
Rating – 4 stars
October 5, 2025
I won a copy of the audiobook through Macmillan Audio’s StoryGraph giveaway which I entered since I really enjoy books surrounding Jewish characters and am also often thinking about my own family’s history and things I may never know.
I would say the book was slow-medium pace, but it was not boring even in the slow moments. There were many characters to keep up with though moreso during the parts taking place in the past, but I found the present harder to keep things straight since there was less focus on who was who and some people were very briefly spoken about in relation to Elijah as compared to Yitz/the past where characters were more developed and involved in the story.
The chapters taking place in the past were very sad and sometimes disturbing but I loved how it was balanced by some dry humor and lightheartedness in the present with Elijah and Eve despite it centering around Eve’s terminal illness. I also related a lot to Elijah and Eve in their experiences as Jewish Americans who were not observant but still felt connected to their Jewish roots.
I would say the book was slow-medium pace, but it was not boring even in the slow moments. There were many characters to keep up with though moreso during the parts taking place in the past, but I found the present harder to keep things straight since there was less focus on who was who and some people were very briefly spoken about in relation to Elijah as compared to Yitz/the past where characters were more developed and involved in the story.
The chapters taking place in the past were very sad and sometimes disturbing but I loved how it was balanced by some dry humor and lightheartedness in the present with Elijah and Eve despite it centering around Eve’s terminal illness. I also related a lot to Elijah and Eve in their experiences as Jewish Americans who were not observant but still felt connected to their Jewish roots.
October 30, 2025
A young man comes home to Chicago to be with his dying mother and learns about his family history, specifically about his grandfather's unsavory past. Although I enjoyed the Chicago setting and some of the Jewish history, I think I'm just sick of "mob" stories at this point.
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.
January 3, 2026
2.5 stars
I won this in a Macmillan giveaway through StoryGraph. Pretty well done; just not my preferred genre. I was interested in this novel because of the genealogy aspect and that resonated with me along with the concept of stories and legacy but overall didn’t really grasp my attention.
I won this in a Macmillan giveaway through StoryGraph. Pretty well done; just not my preferred genre. I was interested in this novel because of the genealogy aspect and that resonated with me along with the concept of stories and legacy but overall didn’t really grasp my attention.
November 16, 2025
I really enjoyed this mobster tale. Family drama, Chicago setting, switching between historical fiction to present day, and some gorgeous turns of phrase to boot. Diamond is a new author to watch.
September 16, 2025
What a gorgeous, true whizbang of a novel.
October 9, 2025
You won't find a more Chicago-ey novel published this year than Jason Diamond's debut, Kaplan's Plot. In fact, Kaplan's Plot is actually two Chicago novels in one -- which makes it as overstuffed with Chicago goodness as a Lou Malnati's deep dish pizza or a walk-off home run at Wrigley Field or a double char dog from the Wiener's Circle. (Sorry, I'll stop now.)
I got to see Diamond at the Chicago release party for Kaplan's Plot a few weeks ago, at which mentioned he always has trouble with his elevator pitch for this novel when someone asks him what it's about. Though he does it very well, I know what he means now. There is a lot going on this book, and it's not easy to summarize succinctly.
But here goes: Kaplan's Plot is about a disgraced tech bro named Elijah who returns to Chicago from the Bay Area after his partners were indicted and his company folded. His mother Eve, a semi-famous poet, is dying of cancer and Elijah decides there's no better time than the present to dig into his family's past. That past? A grandfather (Eve's father) named Yitz Kaplan, a Chicago gangster in the 1920s and 1930s operating from Chicago's famed Maxwell Street. So these two stories intertwine -- Elijah learning about Yitz and his secrets, and Yitz's escapades happening in-scene.
The alternating past-and-present scenes, especially when a character in the present is trying to learn the secrets of the past, is a risky structure. It's difficult to parse out information in a way that makes it still seem surprising and fresh both to the characters and the readers. But Diamond pulls it off here. One thing he does well is make each alternating chapter similar in length -- this may be a personal preference thing, but when I'm reading alternating timelines, and we spend 20 pages in one and then 10 in another, I naturally start caring more about the longer section (and it's a subtle signal the writer does too!). But here both stories are given equal weight, and I think doing so helps make the novel successful.
Plus, compelling characters, a drama-rich plot with secrets and twisty turns, and getting so many great Chicago details in two separate timelines all make this just a lot of fun to read. Not that Diamond's Chicago cred is in question (he grew up in Evanston), but this post on the Chicago Literary Canon on his popular Substack, the Melt, should quell any concerns.
So yes, if Chicago novels are your thing -- or you're just a fan of well-written family dramas -- this one's for you. Highly recommended!
I got to see Diamond at the Chicago release party for Kaplan's Plot a few weeks ago, at which mentioned he always has trouble with his elevator pitch for this novel when someone asks him what it's about. Though he does it very well, I know what he means now. There is a lot going on this book, and it's not easy to summarize succinctly.
But here goes: Kaplan's Plot is about a disgraced tech bro named Elijah who returns to Chicago from the Bay Area after his partners were indicted and his company folded. His mother Eve, a semi-famous poet, is dying of cancer and Elijah decides there's no better time than the present to dig into his family's past. That past? A grandfather (Eve's father) named Yitz Kaplan, a Chicago gangster in the 1920s and 1930s operating from Chicago's famed Maxwell Street. So these two stories intertwine -- Elijah learning about Yitz and his secrets, and Yitz's escapades happening in-scene.
The alternating past-and-present scenes, especially when a character in the present is trying to learn the secrets of the past, is a risky structure. It's difficult to parse out information in a way that makes it still seem surprising and fresh both to the characters and the readers. But Diamond pulls it off here. One thing he does well is make each alternating chapter similar in length -- this may be a personal preference thing, but when I'm reading alternating timelines, and we spend 20 pages in one and then 10 in another, I naturally start caring more about the longer section (and it's a subtle signal the writer does too!). But here both stories are given equal weight, and I think doing so helps make the novel successful.
Plus, compelling characters, a drama-rich plot with secrets and twisty turns, and getting so many great Chicago details in two separate timelines all make this just a lot of fun to read. Not that Diamond's Chicago cred is in question (he grew up in Evanston), but this post on the Chicago Literary Canon on his popular Substack, the Melt, should quell any concerns.
So yes, if Chicago novels are your thing -- or you're just a fan of well-written family dramas -- this one's for you. Highly recommended!
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.
November 19, 2025
As soon as I saw this, I figured it had my name on it. And I wasn’t the only one – two friends wrote to ask me if I’d read it, and one asked if I’d written it under a pen-name.
So, I’m probably too close to this to be objective. I mean, how many other people are writing multi-generational novels about Jewish gangsters set in Chicago and featuring grandchildren trying to learn their grandparents’ gangster history.
To the extent that I can read this without being too aware of how I have chosen to do something so similar in such a different way, I do enjoy the back-and-forth of generations. It’s deliberately not that challenging a braided narrative, and that’s going to play to a wider audience. Diamond sets the scene in each case, and he leaves it to us to weave elements from the past with elements of the present.
We more or less know where things are headed as soon as Elijah finds the cemetery where his great-uncle is buried. It’s contrived to have this history deliberately hidden – as opposed to forgotten – but it’s intriguing from the start. I know how hard it is to sustain a narrative across generations, and Diamond generally brings good energy to it.
By the end,
So, thumbs up to the basics that are going on here. To the degree that I can get outside all that I know about the subject, this works. Go ahead, read it – and wish me luck finding a publisher for mine.
Some historical notes, though. Diamond is reading the gangster crime of Maxwell Street through the lens of The Godfather. He presents Yitz as if he’s a Lansky-like figure, something that didn’t come close to emerging from Chicago let alone from Maxwell Street. I suppose it works in fiction, but I can’t help pushing to correct the record a bit.
In other words, if you’re looking for a story that echoes other gangster stories – that isn’t as radical as I aspire to be – then this also works at that level.
Bottom line, I didn’t write this. But not because I didn’t want to.
So, I’m probably too close to this to be objective. I mean, how many other people are writing multi-generational novels about Jewish gangsters set in Chicago and featuring grandchildren trying to learn their grandparents’ gangster history.
To the extent that I can read this without being too aware of how I have chosen to do something so similar in such a different way, I do enjoy the back-and-forth of generations. It’s deliberately not that challenging a braided narrative, and that’s going to play to a wider audience. Diamond sets the scene in each case, and he leaves it to us to weave elements from the past with elements of the present.
We more or less know where things are headed as soon as Elijah finds the cemetery where his great-uncle is buried. It’s contrived to have this history deliberately hidden – as opposed to forgotten – but it’s intriguing from the start. I know how hard it is to sustain a narrative across generations, and Diamond generally brings good energy to it.
By the end,
So, thumbs up to the basics that are going on here. To the degree that I can get outside all that I know about the subject, this works. Go ahead, read it – and wish me luck finding a publisher for mine.
Some historical notes, though. Diamond is reading the gangster crime of Maxwell Street through the lens of The Godfather. He presents Yitz as if he’s a Lansky-like figure, something that didn’t come close to emerging from Chicago let alone from Maxwell Street. I suppose it works in fiction, but I can’t help pushing to correct the record a bit.
In other words, if you’re looking for a story that echoes other gangster stories – that isn’t as radical as I aspire to be – then this also works at that level.
Bottom line, I didn’t write this. But not because I didn’t want to.
September 25, 2025
Kaplan’s Plot is one of those books that feels like you’re uncovering a family’s history in real time, piece by piece. The story moves between past and present, following Elijah Mendes, a failed tech bro who returns to Chicago after his Bay Area startup crashes and burns. He’s back home to help his mother Eve, who is facing late-stage cancer, and their scenes together are often the heart of the book. Eve is funny, sharp, and, despite the heaviness of her situation, frequently the most entertaining presence in the story.
Through Eve and a stack of ignored letters from the local Hebrew Benevolent Society, Elijah discovers a family mystery involving a cemetery no one in the family even knew they owned. That discovery launches him into the history of the Kaplan brothers, his grandfather Yitz and great-uncle Sol, who immigrated from Odessa to Chicago in the early twentieth century. Yitz becomes a key figure in the Jewish mob, running a bathhouse as his front, while Sol makes his living as a kosher butcher. Their story intertwines with the Irish and Italian underworld, Prohibition schemes, and even a colorful gangster named White Jimmy (who, despite the name, is Black).
The dual timelines of Elijah and Eve in the present and Yitz in the past work well together. The book can be brutal in its depiction of immigrant life in early Chicago, with plenty of violence, but it does not shy away from showing what survival demanded. At its core, this is a novel about family secrets, shame, resilience, and the possibility of healing. Elijah’s research into the past and Eve’s willingness to finally share pieces of her father’s story open up a path for both of them to reconcile with each other and with the choices they have made.
I listened to the audiobook and highly recommend it. The dual narration by Neil Hellegers and Alex Knox brought both timelines vividly to life and made the shifts between eras easy to follow.
Kaplan’s Plot is not a quick read, but it is a rewarding one, mixing mob drama, immigrant struggle, and family reconciliation into a story that feels layered, dark, and deeply human.
Thank you to Macmillan Audio for the gifted audiobook.
Through Eve and a stack of ignored letters from the local Hebrew Benevolent Society, Elijah discovers a family mystery involving a cemetery no one in the family even knew they owned. That discovery launches him into the history of the Kaplan brothers, his grandfather Yitz and great-uncle Sol, who immigrated from Odessa to Chicago in the early twentieth century. Yitz becomes a key figure in the Jewish mob, running a bathhouse as his front, while Sol makes his living as a kosher butcher. Their story intertwines with the Irish and Italian underworld, Prohibition schemes, and even a colorful gangster named White Jimmy (who, despite the name, is Black).
The dual timelines of Elijah and Eve in the present and Yitz in the past work well together. The book can be brutal in its depiction of immigrant life in early Chicago, with plenty of violence, but it does not shy away from showing what survival demanded. At its core, this is a novel about family secrets, shame, resilience, and the possibility of healing. Elijah’s research into the past and Eve’s willingness to finally share pieces of her father’s story open up a path for both of them to reconcile with each other and with the choices they have made.
I listened to the audiobook and highly recommend it. The dual narration by Neil Hellegers and Alex Knox brought both timelines vividly to life and made the shifts between eras easy to follow.
Kaplan’s Plot is not a quick read, but it is a rewarding one, mixing mob drama, immigrant struggle, and family reconciliation into a story that feels layered, dark, and deeply human.
Thank you to Macmillan Audio for the gifted audiobook.
December 30, 2025
I have beef with his plot wrap, but otherwise fine reading. Fine. I had hopes for a good wrap to my year of 153 books, but no.
1) Rose dying by mob action is implied and never resolved. I assume for deep character development we explore generational trauma, but this lands flat like a fart in an elevator. Yes we knew it happened and you had this whole other story to resolve/reveal and didn’t. Fart. Smells. Dissipates without satisfaction.
2) The dad having a second marriage could have been a lot better developed. And I get his plot line was not about his kids at all, but then why bother with the other timeline if it’s ignored. Eve’s trauma is an afterthought mellowed by how high she is. It’s boring. We get it. She smokes pot.
3) Sloppy. Just a sloppy miss on trying to tie it together across generations. One Google search and a scary guy he has lunch with is all this guy has? Boring. Sloppy. He is clearly NOT ACTUALLY Chicago if all he has is a geography map and a distaste for Malort and a drug problem. One lunch with a scary man means he “does right by” him in a paragraph when his grandfather took notes on who was who and where the money was owed and how and why he hated him.
Either you write a book that you want people to enjoy and feel into and you leave them feeling balmed in some way, or you write a really good book and fuck up the ending like King.
This was looking great and then skipped over reality of Chicago politics and even mob action. He got boxes of shit and didn’t review who was who and who owed what? I mean… come on. He clearly needed to pay off the advance or his editor got tired of him.
This is promising like all of King and everyone says. He fucked the ending with really solid characters who could have landed the plane if he had the patience to develop them in a way to do so.
1) Rose dying by mob action is implied and never resolved. I assume for deep character development we explore generational trauma, but this lands flat like a fart in an elevator. Yes we knew it happened and you had this whole other story to resolve/reveal and didn’t. Fart. Smells. Dissipates without satisfaction.
2) The dad having a second marriage could have been a lot better developed. And I get his plot line was not about his kids at all, but then why bother with the other timeline if it’s ignored. Eve’s trauma is an afterthought mellowed by how high she is. It’s boring. We get it. She smokes pot.
3) Sloppy. Just a sloppy miss on trying to tie it together across generations. One Google search and a scary guy he has lunch with is all this guy has? Boring. Sloppy. He is clearly NOT ACTUALLY Chicago if all he has is a geography map and a distaste for Malort and a drug problem. One lunch with a scary man means he “does right by” him in a paragraph when his grandfather took notes on who was who and where the money was owed and how and why he hated him.
Either you write a book that you want people to enjoy and feel into and you leave them feeling balmed in some way, or you write a really good book and fuck up the ending like King.
This was looking great and then skipped over reality of Chicago politics and even mob action. He got boxes of shit and didn’t review who was who and who owed what? I mean… come on. He clearly needed to pay off the advance or his editor got tired of him.
This is promising like all of King and everyone says. He fucked the ending with really solid characters who could have landed the plane if he had the patience to develop them in a way to do so.
This entire review has been hidden because of spoilers.
November 7, 2025
"Leave the piano wire, take the blintzes."
Finding humor in life, even when it's harsh, is a key, to the often violent moments in the family drama Kaplan's Plot, by engrossing literary fiction debut author Jason Diamond.
Ironically, Kaplan's Plot has many plots, from mob life for immigrants in 1920s Chicago to failed tech bro companies in the Bay area to family cemetery plots.
Elijah Mendes comes home to care for his Mother Eve, in the last stages of cancer. He also has nowhere else to go since his tech firm went bust due to unsavory partners.
When Elijah opens unanswered letters from the local Hebrew Benelovent Society addressed to his mother, it leads him to a Jewish cemetery mysteriously owned by his family. It seems Eve has some family secrets. Soon Elijah learns of his mobster grandfather Yitz and Yitz's brother Sol...The Kaplan Brothers. Their story is an immigrant's journey. Not even teens yet, they escape Russia's pogroms against the Jews to America where freedom awaits...or does it?
Voice actors Alex Knox and NeilHellegers
are phenomenal with their Russian, Yiddish and Chicago accents, let alone the emotional depth required to understand the losses this family endures through the generations.
As Eve comes to terms with a father she was ashamed of and son she held at bay; Elijah finds himself at a crossroads where self and family do not have to be separate, and where the plot to the Kaplan's family drama is perhaps forgiveness, togetherness and healing what is wrong to make it right.
I received free copies of this book/audiobook from Flatiron Books and MacMillan Audio via NetGalley for a fair and honest review. All opinions are my own.
Finding humor in life, even when it's harsh, is a key, to the often violent moments in the family drama Kaplan's Plot, by engrossing literary fiction debut author Jason Diamond.
Ironically, Kaplan's Plot has many plots, from mob life for immigrants in 1920s Chicago to failed tech bro companies in the Bay area to family cemetery plots.
Elijah Mendes comes home to care for his Mother Eve, in the last stages of cancer. He also has nowhere else to go since his tech firm went bust due to unsavory partners.
When Elijah opens unanswered letters from the local Hebrew Benelovent Society addressed to his mother, it leads him to a Jewish cemetery mysteriously owned by his family. It seems Eve has some family secrets. Soon Elijah learns of his mobster grandfather Yitz and Yitz's brother Sol...The Kaplan Brothers. Their story is an immigrant's journey. Not even teens yet, they escape Russia's pogroms against the Jews to America where freedom awaits...or does it?
Voice actors Alex Knox and NeilHellegers
are phenomenal with their Russian, Yiddish and Chicago accents, let alone the emotional depth required to understand the losses this family endures through the generations.
As Eve comes to terms with a father she was ashamed of and son she held at bay; Elijah finds himself at a crossroads where self and family do not have to be separate, and where the plot to the Kaplan's family drama is perhaps forgiveness, togetherness and healing what is wrong to make it right.
I received free copies of this book/audiobook from Flatiron Books and MacMillan Audio via NetGalley for a fair and honest review. 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.
September 18, 2025
Veteran novelist Jason Diamond has written a book with multiple timelines. A concept that many authors do not do well. In this instance. Kaplan's Plot exceeds the reader's expectations. The writer takes us through multiple decades, starting from pre-World War I, all through modern times, in Chicago, Illinois. This part of the story is interesting and helps the reader get involved in what turns out to be a most captivating historical criminal procedure novel. The reader is brought back to Chicago, the current day, and Elijah, the protagonist, has returned to help his mother, but his business has gone bankrupt. The two don't get along; however, like most families, they pull together to tolerate each other while Elijah takes care of his mom. He goes through some of his mother's keepsakes and finds old correspondence about secrets in a Family cemetery. As we swing back to 1909, the reader is introduced to Eve's father, Yitz, a Jewish immigrant from Europe who has recently arrived in the United States. As was common during that time, he became involved in Jewish organized crime, which set a precedent for Jewish organized crime during the 50s and 60s, predominantly in Miami and Los Angeles. Kaplan's Plot is a historical novel that the reader cannot put down. I highly recommend it and suggest the reader check out Jason Diamond's backlist.
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!!
December 13, 2025
🎧 4.5⭐️ Loved this book. This starts as a mystery regarding the burial of a person who the current family knows nothing about and the history investigation into the who’s who of the family in two timelines: the present day narrative of the surviving daughter and grandson of one f the brothers and the past story of two brothers who escaped the pogroms of Odessa. We get a wonderful unveiling of the life and times of this immigrant Jewish family and their survival through the tumultuous times of gangland Chicago. There is history, crime, mystery, murder and a wee bit of perfect humor sprinkled throughout. The narration is spot on. Family drama, intergenerational trauma, substance use…but it isn’t sad and bleak.
The only few quibbles I had were that sometimes there seemed to be too much description of events, but in the end, the narration was so well done I couldn’t help nut be sucked in to whatever tangent was being expanded upon. Some side plots seemed unnecessary, but they did serve to inform the character of Elijah. As always, YMMV; give it a chance.
The only few quibbles I had were that sometimes there seemed to be too much description of events, but in the end, the narration was so well done I couldn’t help nut be sucked in to whatever tangent was being expanded upon. Some side plots seemed unnecessary, but they did serve to inform the character of Elijah. As always, YMMV; give it a chance.
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
September 15, 2025
2 1/2 Stars - 30-something Elijah Mendes returns home to help his mother who is suffering from cancer and starts to uncover some long buried family secrets including information about his grandfather, Yitz Kaplan, one of Chicago's Jewish mob bosses. The narrative alternates between Elijah and Yitz. Yitz's story - from his childhood as a survivor of the pogroms in Russian to his immigration to America, two marriages and life of crime - was interesting and compelling but a little hard to follow. I agree with the Kirkus Review: "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 and the Italians. 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 . . . An ambitious novel with a better backstory than contemporary one."
September 14, 2025
Family drama and a decades-old mystery set in the city by the lake.
Elijah Mendes returns home to Chicago after his California startup business implodes amidst legal charges. Though not personally implicated in any crimes, Elijah's professional reputation is in tatters. If that isn't enough, he's also reeling from a divorce and the news that Eve, his semi-famous poet mother, is dying. A chance discovery leads Elijah to start digging into his family's complicated history.
With a story split between Elijah's present-day family research and the narrative of his grandfather Yitz Kaplan's journey from Odessa to Chicago and subsequent rise in the criminal underworld, Kaplan's Plot is am auspicious debut by the author.
4/5
Elijah Mendes returns home to Chicago after his California startup business implodes amidst legal charges. Though not personally implicated in any crimes, Elijah's professional reputation is in tatters. If that isn't enough, he's also reeling from a divorce and the news that Eve, his semi-famous poet mother, is dying. A chance discovery leads Elijah to start digging into his family's complicated history.
With a story split between Elijah's present-day family research and the narrative of his grandfather Yitz Kaplan's journey from Odessa to Chicago and subsequent rise in the criminal underworld, Kaplan's Plot is am auspicious debut by the author.
4/5
November 16, 2025
I wanted to like this more but it’s just sort of mid. The first act is strong, blending together the journey of two young boys from antisemitic Russia to Chicago near the turn of the 20th century with a story of their modern day descendants. There’s a bit of an air of mystery at the beginning as well, about the connection between the family and a small cemetery with unknown residents. But after that everything sort of just happens and it’s not as interesting. The prohibition era gangster stuff is more fun than the modern day protagonists story, but that’s where all the character development happens. It’s kind of doing two things but neither of them to the fullest.
December 20, 2025
3.5 stars. Enjoyable first novel from a very talented writer. Disgraced dotcom entrepreneur Elijah Mendes returns to Chicago to help his dying mother get her affairs in order. Going through her correspondence, he finds a letter from a rabbi and discovers that his family owns a Jewish cemetery. Elijah begins researching his family history and finds out that his grandfather Yitz, who was never mentioned by the family, was a powerful gangster in Chicago's Jewish mafia during the 1920s. Chapters alternate between Elijah's story and Yitz's story and intersect at the satisfying ending when Elijah is able to rectify an injustice decades old.
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.
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