A “scallywag” may be a disreputable fellow, a loveable rogue or a troublesome child.
Its exact origins are unclear, but it seems to be a combination of the very old term “wag” and the Scottish word “scallag.”
“Wag,” in the 1550s, meant “habitual joker” or “rascal.” It may have evolved from
“waghalter,” which meant “gallows bird”—that is, someone destined to swing from a noose—but was also used to refer to impish children or even clocks with pendulums (called “wag-at-the-walls”).
“Scala” began in Scalloway, one of Scotland’s Shetland Islands, which was mostly inhabited by poorer farmers who were often called “scallags.” “Scallag” and “wag” blended as Scottish farm laborers moved to the mainland and joined early trade unions.
Scalloway had—and still does—wild little Shetland ponies. Being small, irritable, and of no use to humans, these ponies were also referred to as “scalawags,” which in that context meant “undersized or worthless animal.” This term also referred to small cattle and sheep, both in Scotland and in the US.
The word first appeared in America in 1848, and referred to trade unionists, ponies, and post-Civil War anti-Confederate Southern white people. As with the term carpetbagger, the word has a long history of use as a slur in Southern partisan debates. It was not associated with pirates until it appeared in novels and plays about seafaring swashbucklers the late 1800s.
Reference works such as Joseph E. Worcester’s 1860 Dictionary of the Caribbean Spanish Language defined scalawag as “A low worthless fellow; a scapegrace.”
In the United Kingdom, the term “scally” is used to refer to elements of the working class and petty criminality. In Philippines, scalawags were used to denote rogue police or military officers.
In my home, when I was very young, my mother referred to me as a scallywag, so you know what kind of child I was!