A friend has asked the narrator to find Simon Wheeler and to ask him about the Reverend Leonidas W. Smiley. Simon Wheeler doesn’t remember a Reverend Smiley but he does start to tell a tale about Jim Smiley, a man who loved to make bets.
We learn from the start that Smiley loves to gamble, but more important perhaps, he likes to bet on animals that don’t seem like they have a good chance of winning. He has an old asthmatic mare that doesn’t look like it can win horse races but always manages to come out on top in the last few seconds of the race. He also has a dog named Andrew Jackson that doesn’t look like he can win a fight – and in fact loses fights until there is money on the table.
One day, Smiley starts educating a frog that he names Dan’l Webster. For three months, he does nothing but teach this frog how to jump higher and faster than any other frog. Then he puts the frog on the market, so to speak, and starts making bets.
One day, Smiley bets a stranger forty bucks that his frog can beat any other frog. The stranger says he doesn’t see anything special about Dan’l Webster. The bet is on but while Smiley goes to get the stranger a frog, the stranger fills Dan’l with quail shot. When the two frogs try to jump, Dan’l can’t even move. The stranger takes the money and leaves.
When Smiley discovers what the cheater has done, that is, when Dan’l Webster burps out quail shot, he starts out after him—but he’s too late. The stranger has disappeared with Smiley’s money.
When Wheeler is interrupted from finishing the story, he tells the narrator to wait. When he comes back, he tries to continue his tall tale but the narrator interrupts and says, not quite good-naturedly, that he needs to go.
The narrator leaves, thinking his quest was fruitless.