When looking at the character the Skipper, or the Shipman, one has to understand whom Geoffrey Chaucer writing about in the fourteenth century. The Shipman was introduced into the Canterbury Tales mainly because of the influence that the sea had on England, and specifically Edward the III's reign. England was a "sea-going people,"" as A Commentary on the General Prologue to the Canterbury Tales points out. The sea was used largely for commercial needs, and both merchant men and the king were in constant threat of foreign vessels that operated with piratical methods.
The tough and prepared Shipman was a strong representative of his class coming from the "urban- folk of The Canterbury Tales. He was from far West Country, maybe even Dartmouth, and these men from Dartmouth during the fourteen century often held blanket privateering commissions (**the king during this day privately hired men to protect his trades and loyal fleets from pirates), and then took the lead for their own piratical methods.
Specifically in this instance, this Shipman is described as a pirate figure that even helps himself to bits of the wine of Bordeaux. The Shipman is cunning, for he knows that he won't get caught for helping himself to the wine. Instead, someone like the Merchant would get caught in place of the Shipman because it was the merchants responsibility for the cargo once it was unloaded.
The original writing states that he is "a good felawe,"" which we would interpret today to mean "a fine rascal."" .
The Shipman is not only a thief, but also a murderer. He explicitly kills other men, as the text explains, "He sent his prisoners home; they walk the plank."" These people most likely drown or get attacked by such sea creatures as Sharks. This would seem preposterous in today's society, but in Chaucer's day ruthless pirates were as common as domestic terrorists are in our lives.
Some criticism offered by A Commentary on the General Prologue to the Canterbury Tales, suggests that "Chaucer implied in the line in the text, of nice conscience, that the Shipman takes no heed whatsoever.