Jim Smiley is an inveterate gambler during California’s Gold Rush days whom Simon Wheeler recalls in excruciating detail. Smiley will bet on anything, to the point where he irritates people, but he is unbothered and obsessed with making wagers. To ingratiate himself with a bettor, Smiley will gladly switch sides on a bet; somehow, he wins anyway. This is not because he is a con artist; instead, it is due to his enthusiastic understanding of all the possibilities—or so claims Simon Wheeler.

Part of the fun of the Jim Smiley story is the possibility that he really is the Leonidas Smiley sought by the Narrator but living under a slightly different name or a nickname. It helps that this Smiley displays a cheerful innocence about others, something that might make sense in a gambler if he were formerly a parson. This lingering possibility helps keep the Narrator, and the reader, enthralled by Wheeler’s depiction of Smiley’s absurd games of chance. In an early version of the story, Smiley’s name was changed to Greeley—a play on “greedy”—but Twain later changed it back to Smiley, a moniker that evokes the character’s innocent friendliness.