This dissertation explores the power that messaging systems play in the symbolic structures of American identity by focusing on the legendary status of the Pony Express in film, literature, commemorative events, and historical site museums. In four chapters and two multi-dimensional installation artworks combining performance, painted sets, and digital viewers, I examine persistent myths surrounding modern American identity and American exceptionalism as articulated through technological development and communications infrastructures. Using a media archeological method to examine the idea of media as message bearers and organizational frameworks, this project engages with theorists of media and modernity from Walter Benjamin and Marshall McLuhan, to infrastructural theorist John Durham-Peters, as well as Lisa Gitelman and Jussi Parikka. Situating the Pony Express as a feature of an American cultural mythology that supports a wide array of twentieth and twenty-first century modes of conveyance, this project seeks to understand what is at stake with the mythological deployment of communications infrastructures past and present. This is a project about the role of media in media history, and the role of absence and historical loss in shaping the underlying meaning of technologies of communication that are themselves portrayed as empire-building entities. Using a mixture of traditional archival methods (spanning rare materials, artifactual collections, official histories) and new media tools (digital code and videography) the dissertation brings questions of virtual communication into the present moment to ask the reader and viewer about the immediate context of our message delivery habitats.