Jan van Eyck’s Virgin and Child with Canon Joris van der Paele, Saint Donatian and Saint George is undoubtedly the most refined and monumental work in his œuvres. The inscription written on the lower frame tells us that this painting was commissioned by Joris van der Paele, a canon of the collegiate church of Saint Donatian in Bruges, and that he founded chaplaincies in the church in 1434, while the painting was completed two years later. Compared to an abundance of controversies over its original location and function, the iconography of the painting tends to be explained as a vision of the donor. This interpretation, however, blinds us to the original context and its reflection on the painting. The aim of my paper is to reinterpret Paele’s Virgin from the point of the donor’s mentality, which is clearly mentioned in the bull of Pope Eugenius IV (8 September 1438). According to the bull, van der Paele’s first chaplaincy granted in 1434 was dedicated to the Virgin, Saint Donatian, Saint George, Saints Peter and Paul, and all other saints. Moreover, it informs us that van der Paele hoped at that time to exchange terrestrial and temporal goods for celestial and eternal ones in order to secure salvation of his and his family’s souls. The iconography of Paele’s Virgin, which was ordered shortly after the foundation of his first chaplaincy, is no doubt reflecting his hope for salvation. As a case study, I suggest that a green parrot held by the Virgin and Child has a crucial meaning within the image. From ancient times, the parrot, or psittacus, was traditionally distinguished from other exotic birds with its green wings and red neck, and especially with its ability to talk. It was considered to greet “ave”, which was connected to the greeting of the archangel Gabriel at the Annunciation in medieval times. In Christian iconography, the parrot came to have more than one meaning, and several interpretations have been suggested about Paele’s parrot: for example, the symbol of the virginity of Mary, the Immaculate Conception, the Word, the eloquence, and the marriage between Christ and the Church. The problem is that these interpretations overlook the context and some characteristic aspects of the painting. To interpret Paele’s parrot, we should consider where it is located in the image to fulfill the donor’s hope for salvation: the parrot is connected here to the womb of the Virgin so as to symbolize that the Word became flesh, or the Incarnation.