As residents of fourteenth-century London, Geoffrey Chaucer, John Gower, and Thomas Hoccleve each day encountered aspects of commerce such as buying, selling, and worrying about being cheated. Many of Chaucer’s Canterbury Tales address how pervasive the market had become in personal relationships. Gower’s writings include praises of the concept of trade and worries that widespread fraud has harmed it. Hoccleve’s poetry examines the difficulty of living in London on a slender salary while at the same time being subject to all the temptations a rich market can provide. Each writer finds that principal tensions in London focused on commerce – how it worked, who controlled it, how it was organized, and who was excluded from it. Reading literary texts through the lens of archival documents and the sociological theories of Pierre Bourdieu, this book demonstrates how the practices of buying and selling in medieval London shaped the writings of Chaucer, Gower, and Hoccleve. Craig Bertolet constructs a framework that reads specific Canterbury tales and pilgrims associated with trade alongside Gower’s Mirour de L’Omme and Confessio Amantis, and Hoccleve’s Male Regle and Regiment of Princes. Together, these texts demonstrate how the inherent instability commerce produces also produces narratives about that commerce.