Simon Wheeler tells the narrator a long, boring story about a man named Jim Smiley and his gambling exploits. Jim Smiley would bet on a sickly horse that always seemed to find a burst of energy at the end of races to win. He also had a bull pup named Andrew Jackson that was unbeatable in fights until it went up against a dog with no hind legs. Smiley's prized possession was a frog named Dan'l Webster that he taught to jump and catch flies, and he made a bet with a stranger to race the frogs for money, only for the stranger to secretly weigh down Smiley's frog before the race, causing him to lose.