Richardson’s Pilgrimage uses illness to examine the operations of sympathy and the structures of care and responsibility. Pilgrimage is, in part, a realization of the aspiration to write a ‘dental novel’, where the surgery setting allows the depiction of a rich and distinctive social world. Consequently, the chapter shows the meaning of illness to be socially and politically determined. Analysis of the mechanisms of sympathy, empathy, and narrative method in the surgery leads to a discussion of public healthcare policy. Pilgrimage reflects the contemporary debate between sociological and moral models of healthcare, exemplified by the Fabian Society and the Charity Organisation Society. Pilgrimage balances, therefore, individual, sympathy-driven care against systematic, disinterested care.