In The Imaginative Prose of Oliver Wendell Holmes Michael A. Weinstein presents a strong case against current critical positions dismissing Holmes as a careless and humorous writer. Weinstein identifies Holmes as a “genteel writer” that partook of the contemporary mistrust of cultural changes and of the longing for order and decency. Dealing with each work individually without losing sight of its place within the Holmes canon, Weinstein incisively shows the ways in which each piece may specialize, focus or expand on “strands of meaning” foreshadowed in other works. Overall, Holmes emerges as a firm believer in self-determination and individual freedom, as well as a man deeply preoccupied with morals and encumbered with existential doubt.

Treating author, subject positions and thematic interests as a single entity, Weinstein discovers in Holmes's works a very modernist notion of reality according to which truth is “a regulative ideal that guides [the individual's] intent” and that cannot escape “the bias imposed by each individual's ‘understanding’”. In allowing different viewpoints to enter his works, Holmes becomes a promoter of free expression and someone aware of the multiplicity of angles, voices and discourses through which it is possible to approach any given subject. Yet Weinstein believes that Holmes is not simply embracing the “sheer continuation of polyvocal conversation”, but simultaneously playing the part of a “reconciler” between poles of experience. So Weinstein calls attention to how Holmes's table-talk discussions exploit subversive strategies.

Despite being aware of the possibility of reading Holmes in the light of twentieth-century aspects of criticism, Weinstein prefers a contextualized reading. Studying Holmes's cogitations on issues such as “the dogma of inherited guilt” or “moral poisoning” in their context, for instance, Weinstein argues that Holmes challenges religious convictions, especially against the “Calvinist will to censure and punish.” Adopting a humanist approach to medicinal science that allows him to move away from the rigid bounds of causality, Holmes appears to expose the psychological damage that can be caused when individuals are held “responsible for impulses and deeds that they cannot control”. Yet Weinstein does not associate the distinction between conscious and unconscious experience in Holmes's work with modern post-Freudian critical structures imposed by modern critics. Weinstein emphasizes how Holmes's advocacy of self-determination as well as of the theory of limited responsibility derives from his own interest in Marshall Hull's theory of animal reflex action which he modified to encompass human psychology.