This note proposes an iconographic interpretation of a small chalk drawing in the collection of the Städel Museum, Frankfurt, Germany – Sleeping Reclining Male Nude with Boy-Genius – (Inv. 393) recently attributed to Michelangelo by Carmen Bambach in Michelangelo: Divine Draftsman & Designer, The Metropolitan Museum of Art, New York, 2017. The subject of the drawing has been heretofore unexplored other than to make general comparisons to Michelangelo’s famous drawing The Dream of Human Life in the Courtauld Collection, London, the so-called Sogno. This note marshals iconographic evidence to suggest that the subject is a sleeping male figure with a possible physical malady being visited in a dream by the healing god Aesculapius represented by a partially obliterated head of a bearded man behind the reclining figure’s left shoulder. This identification is supported by the presence at the right of an ambiguous figure described in the literature as a ‘Boy-Genius’, whose specific attributes, however, permit him to be potentially identified as Telesphorus, the dwarf-like child of the god Aesculapius, whose task it is in Greco-Roman mythology to carry out the cures proscribed by the god in a dream. The proposed theme of this drawing is then associated with the medical origin of the family name de’ Medici as well as the specific Christus Medicus ideology promoted by Giovanni de’ Medici as Pope Leo X, as seen in the frescoes of the Sala di Costantino in the Vatican, Rome.