Unfortunately, this is an impossible question to answer because Chaucer never got to finish The Canterbury Tales. He died before every pilgrim got to share their own stories. In fact, each pilgrim was supposed to tell four tales altogether. Only twenty-four of the proposed one-hundred-and-twenty tales exist, so the entire story was far from being finished when Chaucer passed away.
It is likely Chaucer knew which of the pilgrims would ultimately win. The winning tale might not have even been one of the existing stories, for all we have to go on. However, he left no notes or outlines behind, so the best contemporary critics and readers can do is speculate or choose their own winning tale of the ones that do exist.
The short answer? We don’t know. There is no revelation to who wins the first prize (or any of the prizes) in the story. The background of the story is that a group of 30 pilgrims who meet up on a trip to Canterbury decide to walk together. To pass the journey and make it more...
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