The focus of this chapter is the gambling of the elites and primarily gambling for large financial stakes, so-called playing deep. It seeks to provide a picture of how far gambling of different kinds was firmly integrated in the lives of many among the elites, and how the landscape of elite gambling changed across the eighteenth century. However, it also emphasizes the tensions and even contradictions which existed in elite attitudes towards ‘gaming’ and the influence of different milieu on the propensity to gamble and nature of gambling. At its core are a series of case studies of individual gamblers and specific gambling coteries, including a detailed examination of a case of a junior member of a leading Scottish titled family, Lord William Murray of the Murrays of Atholl, for whom gaming was very destructive personally. Gambling, it is often emphasized, was frequently an enactment of the code of honour of the gentleman; but at stake were different, competing versions of honour and masculinity. Gambling divided as much as it united the elites, in terms of habits, conduct, and attitudes.