In Measure for Measure, Shakespeare’s depiction of Duke Vincentio is often viewed through the lens of moral judgment and ideal leadership. However, upon closer inspection, the Duke’s actions reveal a Machiavellian political philosophy that subordinates morality to political expediency. By analyzing Vincentio's behavior — such as his dissimulation, his manipulation of Angelo, and his use of deceptive tactics like the bed trick — this paper demonstrates that the Duke’s approach to governance aligns closely with Machiavelli’s core principles of realism, thereby, positions Measure for Measure as not only a morality play but also a sophisticated political commentary, reflecting the complexities of governance and leadership as shown in Shakespeare’s political world.