Deceit
Both locals and strangers alike try to deceive each other in this story.
The narrator suspects that his friend’s deceit has led him to be stuck listening to Wheeler’s tall tales, that he is the victim of a prank. Wheeler, in turn, tries to deceive the narrator into believing that his exaggerated stories are true. And finally, when the narrator tries to sneak out of the tavern in the end, he is trying to deceive Wheeler to make his escape.
Smiley sees something in his creatures that others do not see: gumption. The bets he makes require vision, faith, and an enterprising nature. By latching onto these invisible qualities, he calculates that mere appearances will deceive those he gambles with. In the case of Dan’l Webster, he enhances that deception by feigning indifference. This type of deception is very different than that of the stranger. The stranger correctly reads Smiley’s trusting nature and takes advantage of that to cheat—to fill Dan’l Webster with quail shot so he is too heavy to jump, and so can’t compete.
Cunning
Simon Wheeler uses his verbal acuity, a form of cunning, to keep the attention of the narrator, who says that he finds the tall tales tedious, but goes ahead and repeats them anyways to the reader. This shows that you don’t have to be educated to be clever, as the narrator, with his vocabulary full of large words, is easily duped.
Jim Smiley, while he has the reputation of being lucky, is actually a cunning gambler. He observes unique qualities in animals that make them better bets than they appear. And he works to cultivate those qualities. But his cleverness is trumped by the stranger’s cheating. Smiley and the stranger are both cunning, but operate with different ethics in trying to win.
Regional Differences
The story sets up a contrast between an Eastern gentleman, the narrator, and a Western prospector, Simon Wheeler. Twain finds humor in both personalities, and especially in their opposing natures.
The narrator speaks in stiltedly formal and wryly ironic tones, using large words, proper syntax, and excessive good manners. He is the product of the settled industrial East, which had a reputation at the time of being civilized and cultured. He comes off as bemused and at times condescending.
Simon Wheeler tells exaggerated stories in a casual, vernacular style. These tall tales contain colorful characters, rural animals, and dubious ironic twists. Both Wheeler and Smiley represent the qualities of frontiersmen in the West: optimistic, gregarious, unrefined. They get by on cunning and gumption. And they’re perceived by the two visitors as gullible.
In the end, the story entertains because both storytellers are good natured. The narrator is willing to relay how he was duped into listening to Wheeler’s fabrications.
Also, the two political figures alluded to in the story, Andrew Jackson and Daniel Webster—though they were from different regions of the United States, and were often in conflict with each other—both worked to preserve the American union.
