While it always held the connotation of “disreputable fellow,” “scalawag” first referred to trade unionists, ponies, and post-Civil War anti-Confederate Southern white people; it held no association with pirates until it appeared in novels and plays about seafaring swashbucklers the late 1800s.
Scalawag—also spelled scallawag or scallywag, if you prefer—is a remarkable term. Not only is it a rhythmically and visually pleasing word, but it also smacks of salt-sea air and the ruthless carousings of pirates.
As it turns out, however, it wasn’t originally used to refer to pirates at all—at least in the sense that your classic cinematic Golden Age of Pirates, who ruled the seas from the 1650s to the 1730, were called scalawags at the time. Indeed, given its current piratey association, it’s a surprisingly recent word, having first appeared in 1848 in America.
Its precise origins are somewhat unclear, but it seems to be a portmanteau-ish combination of the very old term “wag” and the Scottish word “scallag.”
“Wag,” meaning “habitual joker” or “rascal” from the 1550s, may have been a nominalization of the verb “wag” (c. 1300s), which meant “waver, lack steadfastness,” and was derived from Scandinavian (vagga, “cradle”), Old Swedish (wagga, “fluctuate, rock [a cradle]”), and Old English (wagian, “move backwards and forwards”). These all sprang from the Proto-Germanic suffix wag-, which meant “to move about.” (Hence, obviously, that thing my dogs do when they’re being happy and adorable, a sense that also arose in the mid-15th century.)
Taking a bit of a darker turn, the noun “wag” may have adopted its more mischievous connotation as a shortened version of “waghalter,” which meant “gallows bird”—that is, someone destined to swing (back and forth) from a noose—but was also used in a more playful sense to refer to impish children or even clocks with pendulums (called “wag-at-the-walls”). It is also related to the late 14th-century word “wagger,” which meant “one who stirs up or agitates.”
So, how did “wag” become part of “scalawag”?
It began in Scalloway, one of Scotland’s Shetland Islands, which was mostly inhabited by poorer farmers and other rustic folks who were often called “scallags.”
“Scallag” and “wag” blended as Scottish farm laborers ventured stateside and joined early trade unions, where “scalawag” first emerged as an American English term with its more current sense of “disreputable person” or “low, worthless fellow.”
(Of note: Scalloway was—and still is—also occupied by little Shetland ponies that wandered the countryside. Being small, irritable, and of no particular use to humans, these ponies were also referred to as “scalawags,” which in that context meant “undersized or worthless animal” and also referred to undersized cattle and sheep, both in Scotland and in the U.S.)
But before “scalawag” sailed firmly into pirate territory, it developed another, very specific meaning in America.
From 1862 to the 1880s, it was a pejorative that referred to anti-Confederate native white Southerners or (less commonly) western whites who also supported the Republican Party—which was, at the time, the left-wing American political party, run by anti-slavery activists and the like—and Reconstruction efforts. The scalawags included Southern abolitionists and former slaveowners who supported equal rights after the Civil War, though the word most commonly implied someone of a lower social class.
The word’s use in this sense was likely a result of the fact that the scalawags formed coalitions—rather like trade unions—with black freedmen and recently-arrived Northern carpetbaggers to take control of local governments; it may also have drawn upon that same “back and forth,” dishonest connotation of wag, alluding to the fact that formerly closeted abolitionists “switched sides” after the war. They were thought by pro-Confederacy Southerners to be treacherous, troublesome and threatening to their way of life. (Indeed, Dr. William Closs famously testified that a scalawag was “a Native born Southern white man who says he is no better than a negro and tells the truth when he says it,” during the 1868–69 session of Judge “Greasy” Sam Watts court in Haywood County, N.C.)
However, as the political atmosphere of the South evolved and the memory of the Civil War began to wane, this specific sense of “scalawag” faded while its more general sense of disreputability remained, soon adopting the swashbuckling connotation it still holds today.
As I mentioned before, your typical historical pirate never called him- or herself a “scalawag.” That meaning, it turns out, is entirely thanks to depictions of pirates the performing arts and literature. It’s possible that it was first used in association with the comic opera The Pirates of Penzance, which debuted in New York in 1879; however, plays and novels about pirates were practically a cliché throughout the 19th century, so it seems more likely that “scalawag’s” first use in association with pirates is lost in the pages of some forgotten penny dreadful or play from several years before.
But, as we learned today, while “scalawag” may not have referred to the pirates who historically faced a modern major general, the history of “scalawag” abounds with many cheerful facts of its own.