This chapter will look at the vicissitudes of Cesare Borgia’s reputation by examining some of the more recent research that has appeared on the occasion of the quincentenaries of major events in Cesare Borgia’s life. It also addresses the perplexing question of Niccolò Machiavelli’s apparent admiration of Cesare Borgia and the latter’s use of violence and conspiracy as means of acquiring and building his state. Machiavelli met Cesare Borgia on several occasions in a diplomatic capacity between 1502 and 1503. An analysis of these meetings shows how Machiavelli’s views of Borgia developed from his descriptions in the legations (his diplomatic reports) to the constructed exempla given in his political works. Also worth bearing in mind is the continuing legacy of Machiavelli’s construction. It cuts both ways: Machiavelli’s reputation was seen by some, including contemporaries, as being tainted by his presumed admiration of Borgia, and Borgia’s reputation has been influenced by his association with Machiavelli. The vast scholarship on Machiavelli has often framed his portrayal of Cesare Borgia as the “negative model,” the failed prince, however research on Borgia’s actual administration of the Romagna counteracts that failure. Is the villain of Senigallia and Capua merely a construct, or were his actions within the normal range of sixteenth-century violence and warfare? The current state of research – much of it not yet available in English – allows a more detailed perception of the complexities of a man whose “perpetual good fortune” was not only swept away by events – and finally by poor judgment – but also by the blackening of his family’s reputation.