The dissertation examines Thomas Middleton's political irony in his drama. It differentiates this irony from the broad phrase "Middletonian irony" or the various kinds of irony featured in his oeuvre by observing its connection to what Sir Francis Bacon calls a "crossroads," which produces opera basilica-works for the monarch to resolve. Middleton and Rowley's definition of ironia in The World Tossed at Tennis (1620) in which the eye looks "two ways at once" positions the envisioned royal audience at such a crossroads. In doing so, Middleton and Rowley revise rhetorical definitions of irony that promote an inferred meaning which trumps literal interpretations; they instead favour a third meaning with their analogy of the tailor who stitches two previous habits into a new fashion with his needle. Rulers are thus encouraged to abandon singular, entrenched political habits in favour of new and mutually constituted fashions of governance. The course to which Middleton directs rulers and audiences here and elsewhere resembles the tradition of the via media with its projected balance, but its remaining tension infuses that outcome with the ongoing oscillation of the via diversa. In this manner Middleton's political irony expands upon Bacon's idea of "perpetual renovation" by seeing governance as a theatrical continuum of historical emulation and revision. By resisting the permanence and centrality of authority, my work presents responses to recent studies in political theology, which uphold the superiority of the monarch, and to Middleton criticism's conflicted prescription of either a deliberate intention on the author's part (moral or satirical) or a complete dissolution of meaning. Instead, Middleton uses a didactic allegorical framework that is politically charged but remains ridden with tension. The dissertation's first two chapters observe opera basilica intended for the newly appointed monarch, James I, in The Phoenix (1603-4) and the Lord Mayor of London in The Triumphs of Truth (1613). The final two chapters examine the ways in which Middleton's opera basilica gradually transform into burgeoning citizen politics with The World Tossed at Tennis and his final play A Game at Chess (1624). Although Middleton's message remains equivocal, it is unequivocally political.