Like many inhabitants of booming metropolises, Machiavelli alternated between love and hate for his native city. He often wrote scathing remarks about Florentine political myopia, corruption, and servitude, but also wrote about Florence with pride, patriotism, and confident hope of better times. Despite the alternating tones of sarcasm and despair he used to describe Florentine affairs, Machiavelli provided a stubbornly persistent sense that his city had all the materials and potential necessary for a wholesale, triumphant, and epochal political renewal. As he memorably put it, Florence was "truly a great and wretched city."

Mark Jurdjevic focuses on the Florentine dimension of Machiavelli's political thought, revealing new aspects of his republican convictions. Through The Prince, Discourses, correspondence, and, most substantially, Florentine Histories, Jurdjevic examines Machiavelli's political career and relationships to the republic and the Medici. He shows that significant and as yet unrecognized aspects of Machiavelli's political thought were distinctly Florentine in inspiration, content, and purpose. From a new perspective and armed with new arguments, A Great and Wretched City reengages the venerable debate about Machiavelli's relationship to Renaissance republicanism. Dispelling the myth that Florentine politics offered Machiavelli only negative lessons, Jurdjevic argues that his contempt for the city's shortcomings was a direct function of his considerable estimation of its unrealized political potential.