Jason Diamond

Jason Diamond (born 1979, Chicago) - a contemporary American author and journalist based in Brooklyn, best known for his work in pop culture and Jewish identity. Searching for John Hughes (2016) — A memoir about his obsession with the director and growing up in Chicago. His debut novel, Kaplan’s Plot, follows Elijah Mendes, a disgraced tech entrepreneur who returns to Chicago to care for his dying mother. Elijah discovers a family secret involving his grandfather, Yitz Kaplan, who was a Jewish mob boss in the 1920s. The book explores inheritance, generational trauma, and the evolution of the immigrant “American Dream”. [Google, AI]

Diamond, Jason, (Kaplan’s Plot [hc, Flatiron Books, 2025]) 978-1250385918 [set in Chicago]