The time is 1502 to 1527. As the play opens we are at the famous first midnight meeting between Niccolo Machiavelli, the shy but brilliant first secretary to the Florentine republic—later to write the celebrated political essay, The Prince— and Duke Cesare Borgia, the illegitimate son of Pope Alexander VI. At the time, Cesare commands the papal army dominating the Italian countryside. Seeking to negotiate his city's safety, Niccolo falls under the sway of Cesare's mesmerizing power and unapologetic ruthlessness and is also captivated by Cesare's beautiful mistress, Dorotea Carrociolo. Returning to Florence, Niccolo resigns his official position and abandons his wife and friends to join Cesare in Rome, with plans to ally with the duke in the establishment of a new world order. It is not to be. On his arrival at the Vatican, Niccolo finds the pope assassinated, Cesare near death, and Dorotea in tragic despair. Worse, returning to Florence, he is seen as a traitor by the ruling Medicis and imprisoned and tortured. Finally rescued by his wife, Marietta, and best friend, Biagio, Machiavelli goes into exile, spending his remaining years writing comic plays and political tracts. His plays (which paved the way for the commedia dell'arte) make him famous throughout Italy, but his political tracts, considered scandalous, are suppressed, and his plan to regain political office (in which he enlists the help of Alessandro de Medici, Europe's first black ruler) are unsuccessful. Niccolo must rethink his famous question of whether it is better for a prince to be "loved or feared." Nonetheless, it becomes clear by the end of the play that Machiavelli, although reviled for "telling the truth" about political cruelty and intrigue, has helped unify Italian culture through his essays and dramatic writings. Unit set. Two acts. Approximate running time: 2 hours.