The crusaders’ capture of Jerusalem in 1099 stands as one of the most extraordinary events of the Middle Ages. Such was its importance that it was remembered well into the fifteenth century, including when William Caxton published his Godeffroy of Boloyne, or The Siege and Conqueste of Jerusalem (1481). This paper investigates why Caxton chose to print a story of the First Crusade as the first printed English book on the subject of the crusades. Alarmed by the advance of the Ottomans into Christian Europe, Caxton had printed the book in the hope that the deeds of past crusaders would inspire the book’s readers for two main purposes: first, to incite contemporaries to support the crusade cause; and second, to instil his knightly and noble readers with chivalric values associated with crusading as a means to better themselves. In so doing, this paper demonstrates that the crusades continued to play an important role in the lives and imagination of many of Caxton’s contemporaries, and that tales of Jerusalem’s capture in 1099 alongside news of recent Christian losses were considered persuasive tools for inciting contemporary support for new crusades and military action.