This article recovers the history of Milwaukee modernist Samuel Pessin and his short-lived magazine, Milwaukee Arts Monthly, retitled as Prairie upon a move to Chicago (1922–23). Pessin’s magazine is of contemporary interest for the wide range of figures published in its pages, associated with modernist movements in Milwaukee, Chicago, and across Europe. This history should contribute to the ongoing reorientation of modernist studies away from its conventional geographical and cultural centers. This article is also the first account of Pessin, who has remained a mysterious and marginal figure.