Though Jim Smiley appears to be extraordinarily lucky, it is partly through his cunning and cleverness that he is able to win bets. He is finally outsmarted by a stranger, who beats him through cheating. Nonetheless, the story poses a moral distinction between honest and dishonest cleverness. It also shows that you don’t necessarily have to be educated and well spoken to be clever, nor is a good education a defense against getting fooled.
Although Jim Smiley fools others with his animals, he is not lying to them or cheating them. Thus, he is clever but not deceitful.
Even though Simon Wheeler is uneducated and apparently unsuccessful, he fools the slick "feller" from the East by making him listen to his absurd tales – the narrator is actually the biggest sucker in the story.