"like the fo'castle of a steamboat"
In keeping with the story’s origin in the Tall Tales wing of fiction, Twain chooses to engage some curious similes in the story. Simon Wheeler describes how the dog Andrew Jackson was much different when money was on the line and that his jaw would stick out like a part of a steamboat. One can well imagine Twain the writer or “Mark Twain” the character being familiar enough with a steamboat to make this comparison, but it seems quite odd coming from Wheeler. Perhaps, Twain the writer planted it as a clue to indicate that his own story shouldn’t be taken much more seriously than Wheeler’s. Or, perhaps, it was somewhat poetic way to undermine assumptions about the ignorance of those living on the frontier.
A "frog whirling in the air like a doughnut"
Another curious simile—though for different reasons—is used by Wheeler later to describe the jumping style of a frog in the heat of competition. At first the simile just seems downright odd. How many people have ever actually seen a doughnut whirling in the air and even if they had, would a frog in any way tend to resemble it? The first mystery may be solved by the indication that this time we can probably trust that Wheeler is more familiar with doughnuts than steamships and that in the mining camps of dotting the trail there they probably flew with frequency. The question of how a frog could ever manage to resemble that very specific image may indicate that Wheeler made the whole story up.
Andrew Jackson and Dan'l Webster
Jackson and Webster are chosen as names for the animals for specific metaphorical reasons. The entire story is about the culture clash at play between the sophistication of Easterners and the more earthy and rough-hewn character of Westerners. Although Jackson made his home in Tennessee and that is hardly the “west” today, it most certainly was the far end of the western US before you started getting into frontier territory when he became President. Even by the time Twain wrote the story, those states bordering the Mississippi were still considered more western than eastern. Webster, by contrast, was a highly education, erudite and highly intellectual New Englander. They are stand-ins for “Twain” and Wheeler and the dog and frog are metaphorical stand-ins for them.
Gambling
Gambling is, of course, at the center of the narrative and Wheeler’s story purports to be about a man literally willing to bet on anything. The metaphorical intent is clearly here when extended to “Mark Twain’s” gamble on locating his mystery man by sitting down to hear what Wheeler has to say. He loses that gamble and it is representative of the story’s only real point: everything in life can be boiled down to a wager at some level.
"Leonidas W. Smiley is a myth"
The story practically opens with a flat-out metaphor. Twain tells the reader up front that he is pretty much convinced Smiley is more myth than man. Very few authors have the confidence to telegraph to the reader just a few sentences in that they should probably be prepared to dismiss most if not all of what they are about to be told. Every reader knows that fiction is something the writer made up, but there is an unspoken agreement between writer and reader to overlook this. Why read about something that you can’t at least at some level might just possibly be true or based on something that was true or at least has all the apparent signs of possibly one day coming true. It is an audacious decision to kick off with a metaphor reminding the reader of myth made all the more so in light of it coming so early in Twain’s career.
