Although Castiglione's The Courtier was one of the most popular products of the Italian Renaissance, it has largely escaped the attention of modern political theorists. Many dismiss The Courtier as an apolitical work characterized by nostalgia and escapism, but it should not be so dismissed: on the contrary, Castiglione's book expresses a definite political program. This essay explores that program as a “politics of the second best”—as a pragmatic response to unfortunately diminished political opportunities. Put simply, given the choice between trying to make one's master a better person, on the one hand, and not having a master at all, on the other, surely one would not opt for the former unless the latter was not available. Reflection on this point informs the debate between proponents of “negative liberty” and those of “republican liberty.”