The first three paragraphs of the story reveal the answer to this question. Simon Wheeler was sitting in a chair, dozing, when he was approached by a stranger (the narrator of this story) who asks him if he knows anything about a man named Leonidas W. Smiley. This narrator explains that he's hoping to find out about Leonidas because a friend of the narrator's specifically asked him to find Simon, who might have news about Leonidas.
Well, Simon doesn't know who Leonidas is, but the last name "Smiley" reminds him of a guy that Simon does know an awful lot about: Jim Smiley. So Simon launches into an extremely long story about this guy, Jim Smiley--a story which the narrator has to listen to.
It's very funny for a few reasons! First, there's no relationship between Jim Smiley and Leonidas Smiley, so the story is totally useless to the narrator and wastes his time. You can just imagine the narrator's awkward, impatient expression as the story seems to be wrapping up only to keep on going in another direction. And second, the narrator realizes that his friend has played a joke on him by sending him to Wheeler and asking him to ask about a Smiley. The narrator's friend must have known that this would happen. So, the narrator will probably have a few peevish words to say to his friend the next time they meet.
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