Portraits of Italian mercenary captains (condottieri) constitute a representative part of the earliest 15th-century Renaissance medals. This book discusses their functions, significance and artistic issues, as well as the goals sought by patrons and their advisers through this medium. Why were military leaders particularly interested in having medals made? Was it mere vanity, a form of propaganda, or rather a desire to commemorate their deeds? The first step to answer these questions was to catalogue the 15th-century condottieri medals, date them, analyse their iconographic and literary content, and resolve their political and personal significance. A further step was to find their common features, themes and qualities, both in relation to the group and more broadly. Medals have for a long time occupied in art-historical studies a place similar to where they are often found in museum exhibitions – the side rooms, on the margins of great collections. The present book constitutes one of just a few scholarly discussions devoted to a group of specific medals treated as the main object of study. This book will be appreciated by scholars and enthusiasts of Renaissance art and early modern political history, as well as those interested in medallic art in general, including professionals and private collectors.