The powerful Medici family had a profound impact on a great many lives, but few to the extent of Niccolo Machiavelli (1469-1527). As a leading political thinker Machiavelli personally dealt with the Medici, and as a writer their influence was all the weightier, exemplified especially in The Prince and The History of Florence (Hereafter Istorie); both works in which Machiavelli paid considerable attention to the way the Medici would envisage his work. The relationship between Machiavelli and the Medici is particularly queer, for the Medici were Machiavelli's imagined rescuers from internal exile, yet at the same time his reason for discontent.This relationship is especially important because Machiavelli's work has been given a great deal of credit for the path politics would traverse after his death. This being the case, it is necessary to understand Machiavelli's relationship with the Medici and his views of the Medici family's machine government. As John Najemy quite befittingly wrote, "a long, complex relationship - personal, political, and intellectual - had linked Machiavelli to the Medici." The importance of the link that Najemy speaks of has been echoed by other scholars such as Mary Dietz and Marcia Colish.Perhaps this link so closely tied Machiavelli to the Medici that his place in history would be lost had the Medici failed to rise to power. With this possibility, one must examine Medicean influence over Machiavelli to uncover his true feelings in regards to their rule. Machiavelli was not pro-Medici, nor would he have wanted to be perceived as such, but due to the circumstances that weighed upon Machiavelli while he was in exile, he was required to write of the Medici in either a magnanimous manner, not at all, or with certain doom were he to defy them. Clearly, he wrote of them how they would wish to be perceived in the Istorie, but leaves traces of his true anti-Medici feelings barely noticeable without considerable toil scattered throughout the work. Other works that this essay will examine such as The Prince and his Discourses on Livy hold a less gracious place for the Medici, especially the Discourses which can be viewed as a resounding slap in the face of Medicean rule.It will then be the intent of this work to lay out and explain this complex relationship, drawing on a number of primary and secondary sources. In addition, this work will show the context the Medici has been immortalized in through an examination of Machiavelli's historical writing. As Felix Gilbert correctly points out in his book "Machiavelli and Guicciardini", Machiavelli's Istoire was written in a way that would not offend the Medici, but by concentrating specifically on certain instances (such as the Ciompi revolt) more than others, it is subtly able to convey lessons to a broad audience. An in depth look at the relationship between Machiavelli and the Medici will follow by examining Machiavelli's purposes for writing The Prince, The Art of War, The History of...