Discussions on the nature of leadership—and, specifically, the nature of kingship or sovereignty—are ubiquitous to most historical overviews of leadership studies. This paper suggests that leadership studies would benefit from the use of complex literary and historical analyses, which can then be applied to aid in the understanding of appropriate modern-day corollaries. In particular, the paper presents an interrogation of Shakespeare’s late romance Pericles to examine how early moderns saw the development of proto-democratic ideals. In addition, this paper suggests that Pericles was an open critique of the Union between England and Scotland proposed by King James I in the early seventeenth century. To the early modern English, Union represented the abuse of royal prerogative and the potential loss of English national identity. Finally, the paper concludes by using Pericles and Union to examine the traditions and concerns facing the present-day United Kingdom in the immediate aftermath of the referendum to withdraw from the European Union.