Richard Loeb (left), 18, and Nathan Leopold Jr., 19, after confessing to the murder of 14-year-old Robert “Bobby” Franks, Chicago, 1924. Both went to Stateville Prison in Joliet, Ill. Loeb was killed in prison in 1936 and Leopold was paroled in 1958.

The photo is from “Gangsters & Grifters,” the Chicago Tribune’s new book, which Erin Mystkowski helped edit. See more from the book on the Tribune’s website, and more from the newspaper’s archives on Instagram: @vintagetribune.