The church of St. Francis in Cortona was built in 1245 by one of the most controversial historic figure of the early Franciscan Age, i.e. Friar Elias (ca. 1180–1253), second Minister General of the Order of Friars Minor between 1232 and 1239, supporter of Frederick II and excommunicated by Gregory (1227–1241) in 1240. This church houses an important collection of relics that arrived in the Tuscan town thanks to the effort of Elias himself: a fragment of the Holy Cross, preserved in the renowned Byzantine ivory staurotheke (second half of the 10th century) that he probably acquired during a diplomatic mission to the East, and Francis’ evangeliary, cassock and mortuary pillow. The latter was said to have been donated to Elias and to the newly constructed church in Cortona by the Roman noblewoman Jacoba of Settesoli, member of the Frangipane family and close friend of Saint Francis. Despite their importance as historic and artistic documents telling us both about the role of Elias as intermediate between Byzantium and Cortona and his deep and intimate connection with Saint Francis, these items have been mostly neglected by scholars hitherto. Along with providing an overview on this little-known set of relics and reliquaries, this paper draws attention to a number of problematic issues left unsolved, mostly concerning the pillow, its provenance and its donor.