Green’s Dictionary of Slang

scallywag n.

also scalawag, scallawag, scallowag, skalawag
[? link to Scot. scurryvaig, a vagabond or scalrag, a raggedly dressed person, ? ult. Lat. scurra vagas, a wandering fool]

1. (orig. US) a ne’er-do-well, a disreputable person.

[US]Bartlett Dict. Americanisms 284: Scalawag, a favorite epithet in western New York for a mean fellow; a scape-grace .
[US]T. Haliburton Nature and Human Nature I 112: You good-for-nothin’ young scallowag.
[UK]G.A. Sala My Diary in America I 424: The councilmen too often belong to the comprehensive genus ‘scallywag’.
[US]J.R. Browne Adventures in the Apache Country 183: She [...] had been eight days at this infernal place among a set of scallywags who didn’t understand her lingo.
[US]A.B. Sedgwick My Walking Photograph 12: I can always refer to that other scalawag, my walking photograph. But what a scamp you are, Mr. Richard Robson!
[UK]Leeds Times 25 Mar. 6/5: Wheat had risen ten cents a bushel owing to some scalawags cornering it.
Morn. Appeal (Carson City, NV) 12 Feb. 3/2: Some scallowag punctured General Thaxter’s wheel with pins.
[US]F.H. Carruth Voyage of the Rattletrap 206: If it ain’t them three pesky scallawags back safe and sound!
[US]Watauga Democrat (Boone, NC) 27 Oct. 1/6: ‘A “scalawag” is a native born Southern white man who says that a negro is as good as he is’.
[Aus]‘Rolf Boldrewood’ In Bad Company 107: It’s dashed hard lines on him to be scruffed and gaoled by those Union scallowags.
[UK]‘G.B. Lancaster’ Sons O’ Men 43: Yer was a fair scallywag ter the boys, yer know.
[US]H. Green Actors’ Boarding House (1906) 320: He hearn me, the scalawag!
[UK]Gem 23 Sept. 20: And I guess some of the scalawags down there are feeling a bit chipped now.
[US]T.A. Dorgan Indoor Sports 22 June [synd. cartoon] They’re an awful care them children. My David was a scallywag.
[US]M.G. Hayden ‘Terms Of Disparagement’ in DN IV:iii 204: scalawag, skalawag, rascal.
[UK]J. Buchan Greenmantle (1930) 164: He wrote other letters to the Press, saying that there was no more liberty of speech in England, and a lot of scallywags backed him up.
[UK]‘Sapper’ Mufti 180: Why, in the name of fortune, I should give what I possess to a crowd of scally wags who haven’t made good.
[Ire]L. Doyle Dear Ducks 225: It’s a blessed miracle has fell from Heaven to warn that dirty scallywag from his murdherin’ ways.
[US]J.F. Matheus Black Damp in Hatch & Hamalian Lost Plays of Harlem Renaissance (1996) Scene i: ’Spose yo’ kill that no count scalawag. What good would it do yo’.
[UK]‘George Orwell’ Down and Out in Complete Works I (1986) 193: William and Fred [...] were thorough scallywags, the sort of men who get tramps a bad name.
[US]D. Runyon ‘It Comes Up Mud’ in Runyon on Broadway (1954) 536: Some scalawag slips a firecracker into Governor Hicks.
[US]A. Lomax Mister Jelly Roll (1952) 25: A musician is nothing but a bum and a scalawag.
[UK]P. Kavanagh Tarry Flynn (1965) 23: Good God, good God, what is this country coming to? Atheists, scallywags ...
[US]J. Thompson Criminal (1993) 108: The whole family are liars, malingerers and scalawags.
[Aus]D. Niland Call Me When the Cross Turns Over (1958) 179: You’re a funny little scallywag.
[NZ]J.A. Lee Shiner Slattery 7: Pioneer communities hug their scallywags, as much as their heroes, to their chests, when men meet in the bar.
[WI]S. Selvon Housing Lark 39: These fellars is a set of scallywags, all they could do is waste time, gamble, and chase women.
[US]L. Bangs in Psychotic Reactions (1988) 84: Promising to sign the most outrageous and/or untouchable scalawags from Maine to El Cajon.
[UK]F. Norman Too Many Crooks Spoil the Caper 19: The bad-tempered scallywag reluctantly closed his switch-blade and slowly returned it to his breast pocket.
[UK]G. Young Slow Boats to China (1983) 129: Egyptian scalawags, a grinning lot in torn and dirty robes, perched dangerously on the metal platforms.
[UK]A. Sayle Train to Hell 31: He went all agitated and muttered, ‘Cutpurses! Scallywags!’.
[UK]K. Lette Llama Parlour 10: My mother married ‘beneath herself’. A ‘scallywag’, a ‘larrikin’ [...] my posh aunties from the North Shore suburbs said.
[UK]Sun. Times Mag. 6 Feb. 9: Gary was a scallywag – a bit of a toerag.

2. (US) a white Southerner who was willing to accept the terms of Reconstruction after the US Civil War (1861–5).

Charleston Mercury 9 Aug. 1/3: This invaluable class is composed [...] of ten parts of unadulterated Andy Johnson Union men, ten of good lord and good devil-ites, five of spuss and seventy-five of all scallowags [DA].
[US]Anderson Intelligencer (SC) 8 Jan. 1/6: General Grant is finding favor with Southern Democracy [...] That he should be chosen favorite of the Southern carpet-baggers and scallawags will not surprise anyone.
[US]Waco Eve. News (TX) 18 Sept. 2/2: He would not solicit the colored vote [...] but when the race was between a Democrat and a scalawag-Democrat [...] he was ready to go on the stump.
[US]Salt Lake Herald (UH) 5 Aug. 1/3: The carpet-baggers, the ‘niggers’ and the southern scallywags and scoundrels ruled us after the war until they had stolen everything.
A.M. Simons Social Forces in Amer. Hist. 298: The army of men that were thus marshaling the negroes for the Republican party was made up in part of Northern adventurers (‘carpet-baggers’) and so-called Southern ‘Union men’ (‘scalawags’) [DA].
Democrat 24 Oct. 4/1: It wasn’t this cringing spirit which enabled our forefathers [...] to retain control of the voting machinery and run the scalawags and carpetbaggers out of the state [DA].
[US]Maledicta II:1+2 Summer/Winter 169: Scalawag A native white Southerner who collaborated with Carpetbaggers during the Reconstruction period. Extended to include native white Southern Nigger-lovers in general.

3. (US) the penis.

[US]Alt. Eng. Dict. 🌐 scallywag (noun) penis Origins unknown.

In derivatives

scallywaggery (n.) (also scalawaggery, scallawaggery, scallywagism)

(orig. US) roguery, political opportunism.

[UK]Daily News 7/1: The stages of accumulating merit for the fighting man [...] appear to be first robbing orchards, next hatred of a life at the desk, and finally scallywagism. [...] Robbing orchards and general scallywaggery is not within them [i.e. disqualifications for military service] .
[US]H.S. Harrison Queed 45: The morning Post was an old paper... It had crucified carpet-baggism and scalawaggery upon a cross of burning adjectives [OED].
[US]D. Runyon ‘The Lemon Drop Kid’ in Runyon on Broadway (1954) 381: It is your scallawaggery that makes me so hot.
Nottingham Jrnl 17 Mar. 7/1: We had been left watching while scally-waggery has been going on in Europe.
L. Mosley Gideon Goes to War 139: the time of cynicism, of expediency, of political scallywaggery was not yet passed.
C. Macinnes England, Half Eng. 82: Lake Street, Lagos, was as Hawton had evoked it in his tales of waterfront scallywaggery — a comfortable slum.
[UK]Politics (Aus.) XI 65: Antagonists who fastened on them as convenient symbols of Labor scallywaggery.
M. Wigan Last of the Hunter Gatherers 75: It was more a matter of the companies not policing their own people than scallywaggery institutionalised at the top.
scallywagging (n.)

(orig. US) the act of behaving in a corrupt manner.

G. MacMunn Army 54: In any case ‘scallywagging’ develops invaluable qualities, [...] Scallywagging has the advantage that it can be taken in small or large doses.
(con. 1940) P. Haining Where the Eagle Landed 120: [...] referring to the whole idea as an opportunity for ‘scallywagging’ and the men themselves as ‘scallywags’.
scallawaggy (adj.)

villainous.

[US]Eve. World (N.Y.) 21 June 10/2: [pic. caption] The Scylla and Charybdis of the fair metrop / Are the scallawaggy masher and the noddle-headed cop.