The shipman's tale, and its comic equation of sex and money, has long been read as a commentary on the late medieval merchant. Gardiner Stillwell and Albert H. Silverman saw the Tale as ‘a satire upon the merchant's serious, sober, business-like manner of living’; V. J. Scattergood thought that it was pervaded by a mercantile ethos that the Tale exposed as limited and worldly; others take the view that it portrays the merchant's business practices as dubious and the impact of commerce on individual souls as damagingly sinful. At the same time the Tale's depiction of late medieval bourgeois life and mercantile practices has been praised for its realism and made the subject of detailed economic analysis. However, although the merchant's wife has been recognised as the most interesting character in the Tale, much less attention has been paid to her situation – either as it functions within the narrative or insofar as it reflects the Tale's historical context.

The closest analogues to the Shipman's Tale, Boccaccio's Decameron 8:1 and Sercambi's Novella 19, end with the adulterous wife tricked out of payment for sex by her lover's double-dealings, humiliated by him in her own home infront of her husband and servants, and morally condemned into the bargain. Chaucer's version, by contrast, allows the wife to keep the money, avoid all exposure, and finish the Tale happy and uncensured.