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Scallywag | skalē- wag | also scalawag | skaləˌwag|  
noun  
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informal
a person who behaves badly but in an amusingly mischievous rather than harmful way; a deceitful and unreliable scoundrel; a rascal.

historical  
a white Southerner who collaborated with northern Republicans during Reconstruction, often for personal profit. The term was used derisively by white Southern Democrats who opposed Reconstruction legislation.

ORIGIN mid 19th cent.: of unknown origin.

As useful and interesting as the historical definition is, the informal will be my focus.

 Some synonyms that come to mind for this delightful word are the ones that show up in the definition: scoundrel and rascal. But why end there? Knave, rapscallion, rogue, varlet, villain, scamp, imp, hellion, and monkey all can serve as names for someone who is acting a scoundrel. Of these, varlet was less-than-familiar but has since been initiated into my working vocabulary (I accused my cat of varletry).The other familiar synonyms put a smile on my lips because, hey, I love a good moniker, you villainous, impish knave!

What I wasn’t expecting when conducting my official etymological research of scallywag was the list of terms used to refer to children. Evidently my sentiments toward wee tots are echoed throughout the world (or at least the English-speaking world). Kid, nipper, tiddler, youngster, tike, tyke, shaver, small fry, nestling, brat, terror, holy terror, young ‘un, lad, rug-rat, urchin, ankle-biter, and, guttersnipe all surfaced as possible synonyms for child. An interesting study in diction, perhaps. 
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But back to scallywag. It sounds funny. The -lly reminds me of the word silly and the cadence of the word itself makes me think of polliwogs — a word which I have always found amusing. The original source I consulted maintains that the origins are unknown, but I have seen others that argue the term scallywag, meaning “disreputable fellow,” is an alteration of a Scottish term scallag meaning “a rustic and habitual joker” while yet another insists that its origin is Irish or from some province in Northern England but doesn’t offer much beyond that. Of course these sources are all of questionable integrity, but they do seem to agree that scallywag is a term used to describe those with a penchant for mischief.
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