This research investigates the relationship of material and content in art and craft practices to ask not what things mean but how they mean. The principal object of analysis is the art medal, a form of small-scale, biface sculpture, normally bearing portrait images that was developed in fifteenth century Italy, and that is still practiced today, worldwide. Through the close analysis of a number of art medals, this research investigates the way in which materiality relates to content, and the processes through which meaning is generated. A synthetic methodology is used. This is based on the key methods and beliefs that can be found in numismatic study, in particular connoisseurship, iconography, and - in more contemporary and especially in university study - ideas of agency. This research presents a synthetic analysis of the most canonical expression of these ideas, by Berenson (19021920), Panofsky (19391955), and Gell (1998) respectively. These are set within a broader intellectual framework through analysis of theories of language (Peirce 1960, Saussure 2006), theories of perception (Böhme 2017, Benjamin 19362008a), and contemporary writing on meaning and surfaces (Ingold 2017, Bruno 2014). In this way, the art medal is both the principal object of study, but it also provides the lens through which new understanding is approached, this lens being set within a broader epistemological framework to establish the generalizability of the research findings. There are two objects that are studied in depth. The first of these is the Limbourg Brothers' medal of Constantine the Great. Using the method and ideas developed in the early stages of the thesis, fresh understanding is developed of the role of this medal in the collection of the Duke of Berry. A significant contribution to numismatic knowledge is developed in the demonstration of the medal's dependency on the iconography of Baldwin II, the last Latin Emperor of Constantinople. As a result of this new finding, it is possible to understand the role of the medal within its broader system of other objects, from which multiple meanings are developed through juxtaposition and material handing. In order to bring the generalizable insights of this research into view, the thesis closes with an analysis of the exemplary craft practice of David Pye. It is shown that meaning emerges through a system of movement in which the hand's faculty of touch plays a constructive role. In its conclusions, this research develops knowledge in relation to the intelligence of making as an emergent process within technical systems of humans, materials, and tools. This research challenges future study to direct attention towards the constructive and generative role of touch in art and craft practices. These insights will be vital as we develop new digital technologies of making.