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Thomas Gage, a seventeenth century English priest, traveler, and scholar was the first non-Spanish person to settle in, and travel extensively through, the Spanish Main. After his twelve-year experience as a Dominican in, mostly, Mexico and Guatemala, he returned to England and, after recanting, published his very popular The English-American, his Travail by Sea and Land, or, A New Survey of the West-India’s (1648).The success of this book (which rapidly went through several editions and translations) was mostly due to its coincidence, both in aim and content, with early seventeenth century English colonial ambitions —especially as devised by Oliver Cromwell in his so-called Western Design of 1655— to which it actively contributed. Gage’s successful retrospective construction of himself gained him a relatively influential position in Cromwell’s failed project to replace the Spaniards in the New World. In this paper I will examine how Gage’s insufficiently studied narrative influenced Cromwell’s military project, and will also focus on how this and similar writing produced a number of precarious and self-cancelling identities from which he tried to profit.