A man from the East comes to a western mining town. At the request of a friend, the narrator speaks with Simon Wheeler in order to ask after a man named Leonidas W. Smiley. Instead of giving the narrator the information that he asks for, Wheeler launches into a tall tale about a man named Jim Smiley.
The story goes something like this: Jim Smiley was a man who would bet on anything. He turned a frog into a pet and bet a stranger that his frog, Dan’l Webster, could jump higher than any other frog. While Smiley wasn't looking, the stranger filled Dan’l Webster with quail shot, and Smiley lost the bet. Before he could figure out what happened, the stranger disappeared with the $40 he won by cheating.
Sick of the long-winded tale about Jim Smiley and his frog, the narrator tries to escape from Wheeler before he launches into another story. The narrator realizes that his friend probably intended for him to suffer through Wheeler's tedious tale.