<p>Machiavelli’s <i>Prince</i> has often been the subject of study limited to individual chapters or topics. In this reading, I guide the reader through an alternative route, a deconstructive analysis unfolding chapter-by-chapter, and revealing a dynamic of logical failure of the principalities. A positive moment is regained only at the end of the book where in the <i>Exhortatio ad capessendam Italiam</i> the urgency for a new political leader to constitute a unifying state is declared. This structural dynamic of The Prince allows to postulate that the solution to the crisis of Italian politics resides outside the forms of the same principalities presented in <i>The Prince</i>. In this respect, more support is gained for the connection between the best form of civil popular principality with the exaltation of the Roman republic as treated in Machiavelli’s <i>Discourses on Livy</i>.</p>