This historical contextualization looks at the lack of authority demonstrated by King Alonso throughout the play’s duration through the lens of the historical political theorist, Niccolo Machiavelli, in an attempt to justify that the reason for Alonso’s ineffectual leadership is that he is unable to live up to the standard of a Machiavellian leader: a leader who commands fear, not love, from his subjects. To do so, I examine the evidence for how Alonso rejects the ideals Machiavelli provides for proper leadership, leading to a rule that is marred by his rejection of fear tactics in favor of gaining love, and therefore, a ruling strategy that is ultimately unable to save him from complete loss of power. I also contrast Alonso with Prospero, a ruler commanding by fear the way Machiavelli suggests, and an example of a much more successful reign. In this way, Prospero becomes a version of Machiavelli himself, with Alonso as his antithesis. The essay therefore wrestles with the implications Machiavelli’s treatise has on the play and on Alonso by juxtaposing the king against both Prospero and the context Machiavelli provides for them.