This story of Machiavelli's writings is told through his life in Florence and on diplomatic missions (1469-1527). With impressive mastery of abundant sources, Benner helps us understand his 'extremely ambiguous' writings better. She shows how Machiavelli 'assumed diverse voices and personas, allowing him to engage with different audiences without offending them'. He got his first public position when the Dominican monk Girolamo Savonarola lost power in 1498, a process Machiavelli contributed to. He became a persistent defender of republican freedom, contrasted with what he saw as Medici autocracy. Firmly anti-Medici, he is imprisoned when the family returns to power and ends the republic in late 1512. He settles on his farm in Sant' Andrea in Percussina just outside Florence where he writes his main books. In the distance, he sees Palazzo Vecchio where he had enjoyed power. He writes 'The Prince' – a 'series of mind-teasing conversations', dedicated to Lorenzo di Piero de' Medici – as a 'job application', but we do not know whether the Medici read it. From 1557, all of Machiavelli's works were on the Catholic Church's Index of Prohibited Books for 333 years. Benner writes that Machiavelli was 'a political man through and through', but she prefers not to describe him or his writings as opportunist or stubborn. It is true that 'Machiavelli wrote for all times', but Benner's book may tame our impulse to invoke 'The Prince'. Her erudition raises the threshold for power-legitimising use of Machiavelli. And some of his own words beg caution: 'if sometimes I do happen to tell the truth, I hide it among so many lies that it is hard to find'.