This chapter seeks to better understand the formation of literary-geographical identities and imaginaries by examining the publications and cultural afterlife of Captain John Smith, the explorer, promoter, author, soldier, and self-made knight so closely associated with the beginning of English involvement in North America, and particularly with the original colony of Virginia. The chapter provides a brief overview of the longstanding tendency to see Smith and his works as belonging to, and even a point of origin for, the literature and character of America and the U.S. South, and how this has made him a political and historical lightning rod in highly contentious constructions of North/South identity. To account for this contentious afterlife, but to also move beyond it, the chapter surveys critical approaches that have since better situated Smith’s place in the literature and culture of Renaissance England. Looking at examples from his major works, the chapter attempts to show some of Smith’s experimental structuring and shaping of oppositional and antithetical literary-geographical imaginaries, which he employed to address economic and geographical challenges for the English nation state in the modern colonial and plantation context.