One of Melville's most extensive meditations on the role allotted a writer in the market economy, The Confidence-Man is full of reflexive comments on the nature of writing. These comments have led some recent critics to read the book as an early example of a modernist text that self-consciously announces its status as a fictional construct separated from empirical reality. Paradoxically, however, the novel can also be read as Melville's most realistic response to the conditions of the rising market economy. According to Morton Horwitz, one of the most pressing issues faced by antebellum law was how to distinguish legitimate buying and selling from illegitimate swindles. More than any other antebellum book, The Confidence-Man indicates how arbitrary that distinction is.

Although these two ways of reading the book appear to conflict, they need not. A common theme underlying its many incidents and anecdotes is that things are not what they are advertised to be. This is especially true of the promises made by the country's system of justice, as we learn from a number of characters who have suffered because of its judgments. These explicit examples of injustice are supplemented by numerous examples of people who promise fellow passengers charity and then treat them uncharitably. If Melville's dramatization of the untrustworthiness of the phrase “Charity never faileth” is not an explicit comment on the failure of the legal system, charity did indeed fail as an adequate response to the injustices perpetuated by the legal system's free-agent ideology.