It is hard to imagine that anyone interested in the idea of leadership does not have some passing familiarity with the political thought of Niccolò Machiavelli. Scholarly interpretation of Machiavelli’s thought has generally fallen into three schools. First, there is the old-fashioned view: Machiavelli the teacher of power politics if not political thuggery, a teacher of how to gain and keep oneself in power by any means, moral or immoral. For as he puts it: a ‘prince who wants to keep the state is often forced to be not good’ (Machiavelli 1997, 72).1 A second view is Machiavelli the founder of a realistic modern science of politics, which is to say a ‘value free’ science of politics wherein politics is analysed free from value considerations, and where the reality of ‘what is’ stands conceptually separated from the ideal of ‘what ought to be’. The reason this is so is, as he famously maintains: ‘for he who lets go of what is done for what should be done learns his ruin rather than his preservation’ (Machiavelli 1998b, 61). A third view is that of Machiavelli the Renaissance humanist, a typical representative of the civic humanism that characterized the thought of writers in the Italian Renaissance, who praised the civic virtue of the Roman citizenry and the liberty inherent in its republicanism: a prince who builds his foundation on the people ‘and with his spirit and his orders keeps the generality of people inspired, he will never find himself deceived by them and he will see he has laid his foundations well’ (Machiavelli 1998b, 41).