In Renaissance England, rulers applied the king’s two bodies—the body politic and the body natural—and Machiavellian philosophy to control their states and solidify their political power. In Richard II (1595), Shakespeare responded to the king’s two bodies and Machiavellian philosophy by describing the conflict between King Richard II and Henry Bolingbroke. At the coast of Wales, Bolingbroke’s power, facilitated by the rebellious troops he has mustered, eclipses Richard’s kingship. In the scene at Flint Castle, when Richard’s followers have joined Bolingbroke’s army to challenge the former’s kingly status, his body politic has been threatened; the unity of his two bodies is at the brink of disintegration. At Westminster, Richard eventually gives away his crown as the balm used to anoint a king. Reduced as a man only with a natural body, Richard is deposed. Bolingbroke, ironically, follows Machiavellian philosophy to act like a pious man, making his voyage to the Holy Land. This article argues how the medieval philosophy of the king’s two bodies, focusing on God’s will, gradually shifts to the Renaissance Machiavellian philosophy that emphasizes individual will, by examining the struggle between Richard and Bolingbroke.