A scalawag is a mischievous person who causes trouble or breaks rules, but usually in ways that aren't truly harmful or mean-spirited. When your little brother hides your homework as a prank, or when a friend tells a tall tale about catching a fish “this big,” they're being scalawags. The word suggests someone who's up to no good, but with a playful, roguish quality rather than genuine wickedness.

You might call someone a scalawag affectionately, almost like saying “you little rascal!” A teacher might shake her head at the class clown and say, “What a scalawag!” with a slight smile, because while he's disrupting class, he's not actually being cruel or destructive.

During the Reconstruction period after the Civil War, “scalawag” took on a political meaning in the American South. White Southerners who supported Republican Reconstruction policies were called scalawags by their opponents, who considered them traitors or opportunists. This historical usage carried much more serious negative weight than the playful meaning, and it eventually faded as that era passed.

Today, when someone calls you a scalawag, they usually mean you're a clever troublemaker with charm, someone who bends rules but stops short of real harm.