A priest stands at the deathbed of Richard Whittington, the London mercer and the City's great benefactor, in an illustration of his death in 1423. Poised behind the clergyman (probably the rector of St Michael's Paternoster, Whittingon's parish priest and confessor) stands a physician holding aloft a flask of urine for inspection in the iconic fashion of a medical professional. Whittington's death scene juxtaposes two kinds of expert care that often came into contact in the course of medieval English life. At the bedside, confessors attending to the souls of the dying regularly rubbed shoulders with attending physicians whose expertise might still have managed a cure. The De instructione medici, a guide to medical house visits, recommends that the physician be sure the patient confesses at the start of treatment. (To suggest confession later can only diminish a patient's confidence in the physician and his prognosis.) The surgeon Henri de Mondeville advised battlefield surgeons against removing arrows from wounds before patients had confessed. These medical best practices accorded with ecclesiastical mandate. A decree of the Fourth Lateran Council (1215) instructed physicians to encourage patients’ confession before undertaking medical treatment. In medieval hospitals, where lay care- givers nursed inmates alongside clergy tasked with the cure of their souls, confession was commonplace.

This practical proximity corresponded to a persistent metaphorical comparison between confessional and medical expertise. The Fourth Lateran Council formalized a requirement for all Christians to confess annually, and this decree articulated the spiritually curative task of the confessor by analogy with the expertise of the physician: ‘The priest shall be discerning and prudent, so that like a skilled doctor he may pour wine and oil over the wounds of the injured one.’ The characteristic qualities of the good sacerdos – be discretus, cautus, peritus – are illustrated most saliently by the good medicus. The decree draws this vivid analogy between confessional and medical expertise particularly in comparing their conversation. Careful inquiry (diligenter inquirens) facilitates a discriminating consideration of a sin's circumstances (prudenter intelligat) and then the provision of proper advice (consilium). Discretion and caution, for both confessor and doctor, were aspects of talk. Clerical and lay discourses of confession articulated a form of dialogic examination that proceeded as measured and discerning talk of spiritual disease, and was thus akin to the inquisitive method of a skilled doctor.