This study examines the changes in the portrayal of knights in three early modern Spanish texts: El passo honroso de Suero de Quiñones, El Victorial, and the Historia de los hechos del Marqués de Cádiz. These three works are compared to the rather formulaic examples found in Amadís de Gaula, which contains examples of knights portrayed as exemplary warriors, but that are of one-dimensional fighters exercising a mostly outmoded form of warfare. No longer the centerpiece of the battlefield, real fifteenth-century knights were performing military functions that required them to be not only masters of traditional skills like riding, jousting, and sword-fighting, but also to undergo training in the use of weapons previously reserved for foot soldiers, more consistently lead larger units of troops in battle, and study in order to improve their speaking skills. The best place to observe these changes is in chronicles of the period. They show the emergence of political institutions, the use of larger armies, the employment of better weapons, and the abandonment of the cavalry charge in favor of larger troop movements. These changes occur under the umbrella of emerging humanist ideas about education and war that resulted in part from the translation and circulation of Classical and newly minted military treatises. The result is the immergence of new modes of displaying masculinity for knights.