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Scalawag 

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.
Scalawag by Johnny Rocketfingers November 17, 2003

Scalawag 

A maritime whore; hangs out in ports waiting for sailors.
That chick Tammy's a real scalawag.
Scalawag by Archangel John June 23, 2003

Scalawag 

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

scalawag 

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!
scalawag by Crazy Guy March 28, 2004

scalawag 

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
scalawag by zoddtheimmortall January 13, 2006

Scalawag 

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