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The reign of Henry VII suffers from academic neglect, partly as a consequence of its existence on the threshold of the traditional divide between the medieval and the early modern periods. These are frequently regarded as distinct areas of study, each with its own historiographical traditions shaped by the differing nature of the sources for each. Consequently a significant gap exists in the historiography of the development of both the City of London as a capital city and the English monarchy, and in particular the relationship between them. This thesis seeks to address this lacuna.\ud \ud Using the records of the Crown, the City government and its institutions, this study focuses on the political interaction between the Crown and the City. The first two chapters explore the themes of expectation and political affiliation at the start of the reign and assess the changes and continuities from the Yorkist period. It is argued that Henry’s unfamiliarity with the capital and vice versa led to mutual mistrust which resulted in a confrontation which shaped Henry’s perception of the capital for the rest of the reign. Chapters Three to Five are thematic examinations of key aspects of the City-Crown relationship. Chapter Three explores the financial connections and argues that the relationship fundamentally changed when Henry became solvent and the City lost its leverage with the monarch, as medieval kings had traditionally relied upon finance from the capital. Chapter Four discusses the triangular relationship between the City, Crown and the livery companies. It is demonstrated that Henry favoured some livery companies and suggested that in so doing he sought to dilute the power of the mercantile elite. The mediums and means of communication between the Crown and the City are the subject of Chapter Five, with particular emphasis on key individuals within both the court and the City who facilitated communication between the two. The deaths of these individuals within a few years of each other arguably changed the character of City-Crown negotiations at the turn of the century and helped Edmund Dudley, a man with insider knowledge of the government of London, rise in the king’s service. The final chapter is an examination of the last years of the reign, with particular reference to the key question of the extent of Henry VII’s alleged ‘tyranny’. This thesis reappraises the traditional view that London was particularly targeted in the fiscal 4 exactions perpetrated by the king’s ministers, Empson and Dudley, and challenges the assumption that the subsequent persecutions were purely financially motivated.\ud \ud This thesis argues that this was a reign which saw the reassertion of royal prerogatives and evolution of extant administrative machinery, but little, if any, innovation, at least in the sphere of Crown-City relations. The relationship was pliable and reciprocal, built upon the foundations of mutual need and flexible enough to adjust to the changing demands of Henry and his ministers as they sought to extend the royal prerogative. Claims that London was volatile, particularly at the end of the reign, and likely to rise against the king cannot be sustained.