This article depicts the parallel evolution of the political economies of the “Old Chicago” and Freiburg schools. Both communities within the “laissez-faire within rules” research program and the long-standing “thinking in orders” tradition emerged during the 1930s and culminated in the 1940s, crystallizing around the personalities of Henry C. Simons and Walter Eucken. We show how, in an age of disintegration of national and international orders of economy and society, the political economists at Chicago and Freiburg underwent a double transition: from students of equilibrium to students of order, and from students of various positive orders to defenders of a specific normative order. The vision of the normative order on both sides of the Atlantic was the competitive order and its rules-based framework. Along with shared angst amid disintegrating orders, personal transatlantic connections between the two communities are identified, starting in Berlin during the 1920s. We highlight the role of Friedrich A. Lutz, who, from the mid-1930s to Eucken's death and beyond, served as a lifeline between the isolated Freiburg school and Anglo-Saxon economists. Lutz's activities are embedded in a narrative of transatlantic conversations around Friedrich A. Hayek and the early meetings of the Mont Pèlerin Society.