AbstractCourt dwarfs were a feature of aristocratic entourages across Europe from the Medieval period until the eighteenth century and their presence is recorded in both contemporary artworks and written sources. Traditionally, it has been assumed that these courtly attendants functioned solely as jester‐buffoons who were exploited and humiliated by their patrons, but is this assumption accurate? By recovering the forgotten histories of this significant group of court staff, new perspectives emerge on the lives of court dwarfs and the various roles they undertook, beyond their conventional role as jesters. This article examines the case of Pietro Barbino, a dwarf attendant at the Medici court in sixteenth‐century Florence, who was the subject of a portrait by the court sculptor Valerio Cioli. Information from archival sources about Barbino's life, both inside and outside the court, corresponds with Giorgio Vasari's description of him as ‘a gifted dwarf, well‐lettered, a very gentle spirit and a favourite of our Duke’ (Lives of the Artists, 1568). Barbino's story suggests that, at least in some instances, dwarf attendants were involved with more erudite aspects of courtly entertainment and were able to achieve a measure of personal autonomy within the complex hierarchy of the court system.