Long before the invention of tax evasion, peasants and other lowly characters in the Grimms' Fairy Tales were outfoxing their oppressors, fiscal or otherwise. Sometimes foxes outfoxed their oppressors, too. Though the little guy (or gal) often uses cunning to get ahead, villains also display alarming amounts of cleverness. Other times, the protagonist out-clevers the clever villain. Confused yet? We certainly are. It's like trying to keep track of the pellet with the poison (in the vessel with the pestle).
Clever characters take advantage of social norms by working craftily within them.
Cleverness is used most often by fairy-tale characters to get rich, so it's not exactly the most upstanding quality a character can have.