In his story, Simon Wheeler introduces the narrator and the reader to a real character, a man by the name of Jim Smiley. Simon first met Jim back in the winter of 1849 or the spring of 1850—he can't quite remember which—and one of the things he noticed about him straight away was his almost obsessive interest in betting.

Smiley would bet on just about everything. He was lucky, uncommonly lucky, and he almost always came out a winner. As with a lot of gamblers, Smiley would bet on horse races. But he would bet on the kind of things for which you wouldn't be able to get odds at a race track.

For instance, he used to bet on dog fights, cat fights, and chicken fights. If there happened to be two birds sitting on the fence, this incorrigible gambler would even bet on which one would fly away first. And if he saw a straddlebug, a kind of long-legged insect, he'd wager on how long it would take the little critter to get to his destination.

On a much less savory level, Jim Smiley once bet that the preacher's wife, who'd recently fallen ill, wouldn't get well again, despite her condition having improved.