The two background scenes in Giovanni Girolamo Savoldo’s Saint Matthew and the Angel, currently in the Metropolitan Museum of Art, have been the subject of scholarly debate. This paper presents a new identification for one of the scenes, linking it to an incident in the apocryphal Acts and Martyrdom of Saint Matthew, and further suggests that the other background scene contains either a direct or indirect reference to a passage in Matthew’s account of the Olivet discourse. Furthermore, the composition of the painting has been examined to argue that the painting presents, albeit obliquely, Matthew’s transition from the world of sin and business to that of faith and redemption. The traditional connection of the work to Milanese economic reform and the activities of the Milanese mint, in which the work was originally found, has been challenged, and a new interpretation has been presented that foregrounds issues of charity both in the painting and in Milan at the time the work was made.