Which work did Niccolo Machiavelli write to appeal to the Medici family?

Niccolò Machiavelli wrote "The Prince" with the intent of appealing to the Medici family, who were powerful rulers in Florence during his time. This political treatise outlines methods for acquiring and maintaining political power, demonstrating a pragmatic, often ruthless approach to governance. Machiavelli dedicated "The Prince" to Lorenzo de' Medici as a way to regain favor with the ruling family after they returned to power and he had been removed from his government position. His insights into human nature, the importance of adaptability in leadership, and strategic manipulation of public perception aimed to resonate with the Medici's desire for stability and control.

In contrast, "The Discourses" presents a more republican view of governance, making it less aligned with the interests of the Medici. "Oration on the Dignity of Man," often attributed to Pico della Mirandola, is a different work entirely focused on humanism and philosophy, while "Hamlet" is a Shakespearean play unrelated to Machiavelli's writings on political theory. Thus, "The Prince" stands out as the clear choice in connection to Machiavelli's efforts to engage with the Medici rulers.