“Shakespeare and the Drama of Politic Stratagems” focuses on how Shakespeare dramatically explores strategic issues similar to those discussed by Machiavelli and other early modern politic authors. The thesis is structured in order to tackle the diverse nature of strategy while developing and expanding on its most essential issues. The first chapter deals with the amoral and dangerous political world of the first tetralogy, a world in which one must be strategic in order to survive. Since not every strategist engages in the same kind of strategy or even agrees about what the best strategy might be, the second chapter outlines the different characteristics of Shakespeare’s strategists. These strategists can sometimes achieve success on their own, but no one can survive alone indefinitely, and the third chapter thus outlines the importance of strategic alliances and the dangers of making the wrong alliance. The fourth chapter deals with the numerous kinds of enemies that a strategist must contend with. Not all enemies fight in the same way, so a strategist must be on guard against an enemy’s deceptions, the focus of the fifth chapter. Even if these obstacles are overcome, even the most successful strategists will almost inevitably fail at some point or another. That failure may be due to some flaw in their schemes, or it may be due to the extreme difficulty of achieving success indefinitely. The final chapter deals with the perennial conflict between virtù and fortuna and thus the limits of politic stratagems. Machiavelli’s works can be seen as an epicenter of strategic thinking in the early modern period, and so they act as a guide through complex, contradictory, but ultimately rewarding issues of strategy and their consequences. Machiavelli serves as both analogue and foil, for while Shakespeare dramatizes similar strategic ideas, his dramatizations reveal greater truths about what is at stake when one explores the nature and consequences of politic stratagems. This thesis demonstrates the multiple factors that make strategy so dynamic and useful to a young dramatist in the process of discovering his own interests in the art of politics and the art of drama.