Jason Diamond likes to say he has dual citizenship: though he was born in Chicago and grew up in Lake Forest, he currently lives in Brooklyn.
Yet, for the moment, as I talk to him on a boiling afternoon in July over Zoom, he’s in neither place: He’s hanging out at his in-laws’ in Connecticut a couple days after his birthday—he’s a Cancer, this is important—and recovering from catching hand-in-mouth disease (nope, not foot-in-mouth) from Lulu, his young daughter. Jason’s a new father, a casual emailer who prefers “hey” to “hi,” a nonfiction writer examining everything from Florida to gold chain necklaces, a debut novelist, and someone who, at this point in his career, editors understand will slip in at least one Yiddish word in a story—“It’s just a tick,” he explained. “I’m very proud of everything I am.”
But, like my conversation with Jason, I don’t mean to get sidetracked. Jason’s a rabbit-hole-runner, someone for whom one question can lead down eight different paths (“I have ADHD,” he mentioned halfway through our interview); it’s Jason’s debut novel that we’re here to discuss. Two storylines follow two protagonists in Kaplan’s Plot—which is an apt title containing more than a double entendre, perhaps even a quadruple. Yitz and Elijah live in the 20th and 21st centuries, respectively; Yitz is a Ukrainian immigrant, a Jewish gangster, brother to Sol, and a total mystery to Elijah, his grandson, who’s moving back home to tend to his ailing mother, Eve. What’s consistent? Chicago. Both storylines take us from Lake Shore Drive to Maxwell Street, and Jason even calls his novel “a love letter to the city.”
Our conversation spanned Jewish identity to generational trauma—though it wasn’t my intention to put Jason on the couch. Curious and unafraid, Jason’s interested in digging into his family’s past to not only understand himself better, but to fictionalize on the page. “It’s a very strange thing that we try to hide from the fears and sins of our ancestors,” he said. “Because they’re in us, you know.”
This conversation has been edited for grammar and clarity.
Ruby Rosenthal
I wanted to ask you about being a “Jewish writer,” because much of what you write about has to do, in some way, with Jewish identity. And I know many people don’t like being put in that kind of a box, but I’m wondering if that was ever a conscious thought of yours—like, “I want to cover Jewish things”—or whether you more or less fell into it?
Jason Diamond
My Jewishness has always been so important to me, it’s the only thing I’ve ever carried my whole life. My dad’s family are Holocaust survivors, and my dad himself is a displaced person, so I was raised with a lot of awareness of this stuff. When my dad was growing up—after he came to America—I think part of his regiment for learning English was the Marx Brothers movies, so that’s ingrained in my psyche, in my DNA. You couldn’t deprogram me to be anything but who I am. So it just comes out in my writing.
But from an early age, my mom tried to explain to me that there are people who won’t like me because of who I am, and when you’re six, that’s mind-blowing. Like, I was watching Mr. Rogers, who was telling me that everybody’s special!
Ruby Rosenthal
I think it’s so unfortunate, but very universal, that parents will tell kids of any kind of minority, there are going to be people that don’t like you just because of who you are.
Jason Diamond
Once you start kind of understanding that a little bit more, it kind of gives you a bigger view of the world, making you realize maybe there’s a sameness to us all.
That’s how I came to both define myself and my Jewishness, but also define my humanity by understanding that there are these deep-seated hatreds that make no sense, and they’re based out of fear and ignorance. Those things define the human condition, unfortunately. Part of my being a Jewish person—and everything I do, whether it’s writing, or teaching my daughter how to be a human—is, “Hey, we’re all the same, and there’s nothing wrong with anybody for being anything.”
Ruby Rosenthal
I’m curious if you took those words from a young age and if it propelled your writing, or if you remember the first Jewish thing that you wrote where you felt like, “Oh, this is me. This is what feels most natural.”
Jason Diamond
So this won’t totally answer your question, but I was a big reader from a pretty early age. I had a teacher in high school who was always trying to get me to read other stuff, and one day, she gives me The Metamorphosis, and told me to write two pages about what I thought.
I basically wrote a review, saying how funny I thought it was. In the library before I turned the paper in, I was reading about Kafka, and realized, “Oh, he’s Jewish;” I have something in common with this guy. I remember turning it in, and the look on my teacher’s face said, “You thought it was funny?” And I was like, “Isn’t that the point?” I think something about that tipped me off that I was tapping into something that she didn’t get. She was Irish, and I remember being a kid and thinking, “It must be a Jewish thing.”
I do think Kafka is hilarious still, but that was the first time I ever felt truly understood by declaring that I thought Kafka was humorous, in the grand tradition of Jews being funny. That blew my mind. That set me down a path of not just looking at things through a Jewish lens, but also how can I look at other things from a different angle? You just start to notice these things, and you’re like, “Oh boy, I look at everything through this, don’t I?”
Ruby Rosenthal
Your teacher not understanding your perspective makes me think of how often non-Jews don’t get Curb Your Enthusiasm, they’re like, “Why is this funny?” There’s no way to explain it, you know?
Jason Diamond
Larry David, Franz Kafka, Mel Brooks, Richard Lewis, Gilda Radner—all Jewish Cancers, like me—those are my guiding lights. I want to be able to sort of feel what they’re feeling by creating something so interesting and weird.
Some people won’t get it. And then some guy named Murray will be like, “What are you talking about? Of course, I get it. Who doesn’t get this?” Some people think I’m joking, or they’re like, “How are you so Jewish?” This is just who I am.
But I stopped reading anything that would have influenced me when I started writing the book—I don’t want to copy anybody.
Ruby Rosenthal
You completely stopped?
Jason Diamond
Well, when I was trying to write about Yitz falling in love again, I was like, “How do I do this?” I remembered there was a Grace Paley story [I loved] that just popped into my head, so I went and reread that, and realized, oh, okay, this is what I need to do. And I switched it from his perspective to hers.
It’s funny, I’ve tried to write novels—I’ve gotten through a first draft maybe twice. But I’ve never been in it for the long haul. But this time, I was in it, and realized I can unlock these things. And if I pick a book off my shelf, Grace Paley can take me to this place, and help unlock my own way of doing it—it was just incredible.
Ruby Rosenthal
That was my favorite part of the book—her perspective shows us Yitz in such a different light. Then, we can understand Eve better, as well as understand Elijah and Eve’s relationship in a different way.
Jason Diamond
That’s the thing I was trying to put across. The point of the whole book is the choices we make. It’s so mind-blowing to think that, like—obviously you and I are not bootleggers, and we’re not, you know, having people murdered—
Ruby Rosenthal
How do you know?
Jason Diamond
Yeah (laughs), I guess I don’t know. The people in my family have made so many bad decisions, and I know a lot of those affected me, and they affected my mother, they affected my father, they affected my grandparents. And sometimes I think about how choices that happened forty, fifty, sixty, a hundred years before my birth, could have spelled an earlier end, or a sadder life for me.
Our ancestors probably made choices they didn’t want to make, or wouldn’t have made if they’d been given other options. I believe those choices affect us all these years later because it gets passed down.
So that’s what I was really fascinated with: Yitz comes to America, and the only option he has is this path. Sol is someone people will look at and say, “Oh, well, one’s good, one’s bad.” It’s not about that—they’re just different people. Yitz is a little more instinctual, he’s in survival mode all the time.
Ruby Rosenthal
That’s right, Yitz says that his whole life has been about survival. At the same time, there’s so much secrecy in the book. Everybody’s hiding something from somebody else, and the older family members in the book were holding on to so much. Then, it seems, the trauma from holding on and not sharing gets passed down. Was it your intention to have secrecy in this way?
Jason Diamond
Part of that was stuff I’ve been internalizing my whole life with my own family—I’ve had to pry and pull my family to explain things to me. I remember when I was about eight years old, I went and stayed with my grandpa—I loved my grandfather. He was the sweetest guy—and one night, I remembered I was playing because he had gone to sleep, and I noticed, oh my god, there’s a gun behind this chair.
I didn’t know what to say, and so I went to my cousin, who told me Grandpa Julius is scared the Nazis are coming back. And so that was survival, that’s who he was.
In me, it manifests itself in smaller things. Like, I have to be working all the time—it’s not the same thing, but I feel like it gets passed down, and filters itself into different ways. Now I have a daughter, and I’m watching her, wondering how free of this stuff she’s going to be.
Ruby Rosenthal
It’s impressive to already have the foresight to wonder how you can make sure that she has as little of this as possible.
Jason Diamond
We don’t understand enough about the trauma we inherit to begin with, and it’s so hard to figure out how to say anything intelligent about it.
Generational trauma was always going to be [in the book], because while I wanted to write a book that had gangsters in it, the best stories about organized crime always say something. They talk about America, they talk about family, they talk about masculinity, they talk about racism—that’s what I wanted to do, I wanted to talk about intergenerational trauma, the things we inherit.
Ruby Rosenthal
I think you did it, and you did it well, especially from a Jewish angle, because I know I have never read anything Jewish about gangsters. And I think it will sit well with a lot of people, because while everybody has some kind of generational trauma, not everybody is willing to look at themselves and say, I dealt with this, and I’m going to make sure it doesn’t affect other people.
Jason Diamond
Trauma is very deep; it’s a tough thing to analyze, especially when it gets turned into clinical science. I think that’s the beauty of fiction: it gives people an opportunity to sort of engage with it in a different way. That’s why, when it’s done right, I really appreciate anything that analyzes something as complex as trauma, and I’m that’s what I’m hoping people take away from the book.
The Chicago Review of Books is excited to co-host the Chicago release party for Kaplan’s Plot! Join us on Friday, September 19 at 7:00 at Volumes Bookcafe for a conversation between Jason Diamond and Chicago icon Jami Attenberg!
FICTION
Kaplan’s Plot
By Jason Diamond
Flatiron Books
Published September 9, 2025
