John R. Palandech was a well-known immigrant publisher, politician, and entrepreneur in Chicago from the Gilded Age to the post–World War II era. This article retraces his biography and crosses it with the transatlantic political, cultural, and economic world Palandech was a part of and actor in. At the core of this study is a collection of letters sent by Palandech to his brother Joko in the Bocca di Cattaro region (today Montenegro). Complemented with archival and newspaper material, this article discusses the social personae JR Palandech took on as an immigrant entrepreneur and leader, an eminent citizen of Chicago, and as a son, brother, husband, and father.