The tale-telling contest is the brainchild of the man, usually referred to as the "Host," who runs the Tabard Inn in Southwark where the pilgrims meet. The Host's real name is Harry Bailey. He talks to the pilgrims and proposes a game:
...as ye goon by the weye
Ye shapen yow to talen and to pleye
The Host then stipulates the rules of a tale-telling contest:
And which of yow that bereth hym best of alle,
That is to seyn, that telleth in this caas
Tales of best sentence and moost solaas,
Shal have a soper at oure aller cost
Heere in this place, sittynge by this post,
Whan that we come agayn fro Caunterbury.
And for to make yow the moore mury,
I wol myselven goodly with yow ryde
Right at myn owene cost, and be youre gyde;
And who so wole my juggement withseye
Shal paye al that we spenden by the weye.
Each pilgrim has to tell two tales on the way to Canterbury and two more on the way back. The Host himself will leave the inn and travel with them in order to judge the contest, and when they return to the tavern after having been on their pilgrimage, the person he judges the winner will eat supper (probably at his tavern) paid for by all of the other pilgrims. Who will the winner be?
That is to seyn, that telleth in this caas
Tales of best sentence and moost solaas
(797-8)
Sentence is moral sententiousness, or moral instruction. Solaas is entertainment value, fun. These are two totally different criteria. But the answer to your question is the Host. Incidentally, we never find out who won the contest!
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