Term first coined in the late 1800s by Southerners who had Northerners exploit the cheap land during the Reconstruction. Also known as carpetbaggers. Most recently, it is used to describe Northerners who buy cheap land from Southern coastal towns, develop the area, and then resell the land for a much higher price.
Those damn scalawags are taking over Florida!
by Crazy Guy March 28, 2004

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Top Definition
A scumbag and a traitor. First used during the reconstruction era South for White Southerners who supported the Carpet Baggers.
"You're nothing but a dirty scalawag", said Henry.
by OneBadAsp October 20, 2006

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1) A rascal.
2) Word used by Strong Bad at the end of his little song about the difference between "its" and "it's".
If you want it to be possessive, it's just "ITS." But, if it's supposed to be a contraction then it's
"I-T-apostrophe-S," scalawag.
by Johnny Rocketfingers November 17, 2003

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a woman of free sexual behavior.

That scalawag took the whole 9.
by Anonymous October 11, 2003

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A maritime whore; hangs out in ports waiting for sailors.

That chick Tammy's a real scalawag.
by Archangel John June 23, 2003

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primarily white people that were in support of the union between the north and the confederate south.
Theym daymn scalawags, we wants to keeps our slaves and sisters in our beds. -Robert E. Lee
by zoddtheimmortall January 13, 2006

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a very nice girl
"yo, you just out the penetentiary? that tammy is a scalawag."
by Anonymous October 11, 2003

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