Walter Raleigh (also called Jonah and the Whale) pipes depict a bearded human head being swallowed (or disgorged depending on your glass half full vs half empty mentality) by either an alligator or a whale (again, depending on your interpretation). The motif can be interpreted as either representing the Biblical story of Jonah being swallowed and regurgitated by a whale. This is an allegorical tale of a man named Jonah who was commanded by God to preach repentance to the wicked city of Nineveh. Instead of following God’s orders, Jonah fled on board a boat, which was soon caught in a violent storm. In order to save the crew, Jonah threw himself overboard and the seas calmed. He was swallowed by a whale and carried for three days in its belly. After being thrown up onto dry land by the whale, Jonah proclaimed “Salvation comes from the Lord” and went on to preach to, and save, the city of Nineveh. The smoking of a pipe, often even in the 17th century seen as a bad habit, in the wilds of the New World, while looking at the face of the prophet Jonah may have led to quiet reflection of the fate of the smoker’s soul.
The other story that is more often associated with this style pipe is that Sir Walter Raleigh, the man who is said to have introduced tobacco from the New World to England, smoked so much, that his body and clothing were literally soak in the juice of the vile weed. Once when riding in a boat in Virginia, Raleigh is said to have fallen overboard and was swallowed by an alligator (as crocodiles don’t exist north of Mexico it must have been an alligator and not a crocodile as is often mis-reported). being so tobacco juicy, the alligator immediately threw him up, thus saving his life and perhaps causing Raleigh to exclaim “Salvation comes from the tobacco”. While smoking a pipe that had what you interpreted as the figure of the prophet Jonah on it may have caused you reflect on your wretched tobacco soaked life, smoking one with what you saw as Walter Raleigh may have made you say “Dude, look at me, I’m drinking tobacco from the head of a dude thrown up by an alligator!”
The decoration is either molded in high or low relief on both the bowl and the stem. They were produced by the Dutch from ca. 1630s to the end of the 17th century. They are known to have been found on one other Massachusetts site, the Ezra Perry II homesite (aka the Aptucxet Trading Post) in Bourne, at the French sites of Champlain’s Habitation in Nova Scotia and Pentagoet in Maine, the English site of the Clark and Lake Trading Post in Maine, and at the Dutch site of Fort Orange (Albany) in New York. These pipes appear to be associated with sites related to trading with the native people and may have been items specifically made for Native trade. The effigy nature of the pipe, with the face on the bowl facing the smoker, is placed in exactly the same way that Native made effigy pipes are, with the face facing the smoker, and the theme of a monster swallowing and throwing them up would have fit in well with Native beliefs. Add to this the chance one would have to preach to the Native purchaser about the Salvation through God and you have an instant hit with all parties involved. Plus, whoever buys it gets to smoke tobacco out of the head of a dude who was thrown up by either a whale or an alligator (depending on your attitude at the moment).