The meaning of the two lines in the Prologue that refer to the Shipman's yearly trips to Bordeaux with the wine fleet—

—has long been a source of uneasiness to students of Chaucer, an uneasiness which arises in large part from the tone of the rest of the portrait. Since we are told that this man of Dartmouth who sailed the Maudeleyne was without peer as a seaman and without mercy as a pirate, we expect greater knavery than a purely superficial reading of the lines indicates—that the Shipman drank some of his cargo at night. The desire for an interpretation appropriate to the Shipman's general nature led Skeat so far as to suggest that he was a smuggler as well as a pirate: “Very many a draught of wine had be drawn (stolen or carried off from Bordeaux, cask and all) while the chapman (merchant or supercargo to whom the wines belonged) was asleep.” While most of the more recent editors take it for granted that the Shipman's thieving had to do with the legitimate cargo which he had on board, their uncertainty as to its significance is evident in such a gloss as “The shipman stole much of the wine which he was carrying for a merchant; he extracted, in other words, some of the cargo.” The disparity here between the “much” of the first clause and the “some” of the last one is a nice example of the persistent hesitance about Chaucer's meaning.