This finely worked and intensely naturalistic drawing belongs to a small but distinct group of red chalk portrait studies of Fra Bartolommeo’s Dominican brothers. These sheets were drawn on a small scale with exquisite skill, the artist stumping and rubbing the chalk to render the facial topography and minutely subtle effects of light. The drawings served the artist in his work on five fresco lunettes depicting Dominican saints, painted over the doors of the visitors’ sleeping quarters (the Forestiera) on the ground floor of the convert of San Marco, Florence.