With the birth of the Order of St Jerome in 1373 we witness the last and possibly the most successful epigone of the monastic movements that arose in medieval Europe. But how did one of the last orders to be born in the Middle Ages manage to become, all of a sudden, a core element for the visual and spiritual articulation of the new Castilian hierarchies? This book is aimed at answering this question and, through a careful analysis, it sheds light on a series of aspects concerning the Order of St Jerome which so far had only been studied in isolation: the inception of identity narratives through artistic patronage, the negotiation of memorial spaces within a complex monastic topography and the use of different artistic languages for the articulation of diverse devotional discourses. This journey will lead us to monasteries such as Lupiana, Guadalupe, Fresdelval, Valparaíso and El Parral, and it will offer us a new way of understanding the dynamics and tensions that characterised the strong bonds that connected the Castilian elites to the spiritual landscape of the time.