This chapter takes up Daly's civic role in influencing American commercial expansion via promotion, acceptance, and development of large-scale American transportation systems. Particularly as geographical President Daly's authoritative voice and seasoned knowledge carried a great deal of weight within debates over the selection of competing rail and water transportation routes in the nineteenth-century heyday of big schemes and the enormous 'empire of wealth' to be created by them. Such debates centered upon numerous physical geography, political, economic, technological, and social questions and concerns, particularly about the 'best' routes to be developed. The chapter focuses specifically on two of Daly's own pet schemes: his associations with the Northern Pacific Railway Company (NPR) in the western United States, and with the Nicaragua Canal Company, an entity that competed for, but ultimately lost, the rights to build a shipping canal across Central America at Nicaragua.