Two animals prove essential to Smiley’s betting career: a decrepit bulldog named “Andrew Jackson,” after the famous United States president (1767-1845), and a frog named “Dan’l Webster” after the famous orator, attorney, and politician Daniel Webster (1782-1852). Twain’s contemporary readers would have immediately recognized these references, and although Twain makes no specific thematic comparisons between the animals and the men, these references emphasize Smiley’s silly-yet-savvy nature. Humorously, Andrew Jackson and Daniel Webster where political rivals, indicating that the names were chosen by Smiley without any particular political consideration. Instead, Twain allows Smiley to symbolically reconcile America’s regional and political divide for the purpose of increasing his own wealth.

The motif of Smiley’s increasingly ridiculous bets form a running joke throughout the story and contextualize his significant losses with Andrew Jackson and Dan’l Webster. Often, Smiley’s bets feature animals. According to Simon Wheeler, Jim Smiley would bet on anything and possessed “rat-tarriers, and chicken cocks, and tom-cats, and all them kind of things” (Paragraph 7). This long list of creatures, plus a horse so slow that she was known locally as “the fifteen-minute nag” (Paragraph 5), emphasize the rural setting of the story and Smiley’s willingness to eschew social norms.