the definition of scaliwag, according to the inventor of the word, is whores that got picked up by pirates and other sailors in port. Then got fu*ked in every oriface imaginable, using any and every available blunt object (specifically including the pepper shaker). When the whore was so utterly abused and disgusting that nobody wanted to touch her, the sailors would just throw her overboard.
A low-life from a trailor park. This type of person most likely will be seen with Circle K Feet and a Kool-Aid smile. It's also a term to describe a loose or easy female. Another name for someone who is a professional bowler with a bad combover.
Two scaliwags were arrested in the trailor park last night for stealing a 10-speed.