In this essay I revisit The Prince and the Discourses and argue that across the design of these two texts on the theme of conspiracy Machiavelli constructs an ambush on Medici princes. I reconsider Mary Dietz’s (1986), and Langton’s and Dietz’s (1987) suggestion that Machiavelli’s The Prince was a deceptive political act through an exploration of the link Dietz and Sheldon Wolin (2004) draw between Machiavelli’s method and Renaissance artistry. I suggest that Machiavelli applied a one-point linear perspective – a scientific and visual method of pictorial representation and geometrical modelling that emerged for the first time in the Renaissance – to the political field. I test this hypothesis on the theme of conspiracy in Machiavelli’s work by arguing that The Prince ultimately presents one vantage point – that of the prince–while the Discourses offers another – that of the conspirators. I argue that a blindspot is created by these two texts when they are jointly considered: conspirators seduced, recruited, and trained by the Discourses eliminate a prince caught off guard for having followed the advice on conspiracy in The Prince.