This essay attempts to connect the two sides of the American arts administrator Michael Straight’s activities. At Cambridge University in the 1930s Straight had been recruited as a Soviet spy. Later a deep interest in the arts led him to form a collection of paintings and drawings from which he donated the portrait of Giovanni Borgherini and his Tutor to the National Gallery of Art, Washington. At the time his espionage was exposed in the 1960s, Straight had the painting, dubiously attributed to Giorgione, X-rayed. Beneath the painted surface appeared a radically different conception for the boy’s head, which can, in fact, be associated with Giorgione. The contemporaneous unveiling of Straight and of Borgherini raises questions about the identity of the sitter and the collector that may help to explain Straight’s fascination with the picture.