This article examines the character of John Hynde Cotton, a leading tory opponent of Sir Robert Walpole, who played a particularly puzzling role in the conspiracies behind the Jacobite rebellion of 1745, and the parliaments of George II. Entering a coalition ministry in 1744, he was immersed at the same time in intrigue with the exiled Stuart court, and at one stage pledged to use resignation from government as the signal for rebellion. The article explores the background to his career, tracing the intellectual, professional and kinship networks into which he was pressed, and their impact on his political commitments. Cotton's views on government and society were the product of a man caught up in a conflict between image and reality, torn between a set of different identities: robust doyen of rural squiredom, political and commercial ‘insider’, scholar, and ideologue shaped profoundly by the politico-religious crises of the previous century. The article aims to stimulate a new analysis of the facts of a tory-Jacobite career, and so enhance a debate that is in danger of appearing stale. It aspires to reach a deeper understanding of the meaning and principles of eighteenth-century toryism, beyond the mere counting of ‘Jacobite’ or ‘Hanoverian’ heads.