Kaplan's Plot, by Jason Diamond: A Big-Shouldered Debut

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!