1841, Letter to the editor, The Southern Planter, Volume I, No. 1, January 1841, p. 12,
The next year I had a projecting kind of jack leg carpenter, from Hanover, living with me in the capacity of overseer […]
1941, Martha Colquitt, Interview published in Slave Narratives, Library of Congress Project, Volume 4: Georgia Narratives, Part 1,
Grandma didn’t think chillun ought to see funerals, so de first one I ever seed, wuz when ma died two years atter de War wuz done over. A jackleg colored preacher talked, but he didn’t have sense ’nuff to preach a sho’ ’nuff sermon.
1957, Frederik Pohl and C. M. Kornbluth, Wolfbane, Chapter 11, in Galaxy Science Fiction,
He was a doer, not a thinker; his skills were the skills of an artisan, a tinkerer, a jackleg mechanic.
(US) Dishonest, unscrupulous.
(US) Ineptly built or operated; makeshift.
2005, William Hoffman, Lies, Montgomery, Alabama: River City Publishing, Chapter 23, p. 226,
Driving the secondhand Chevy pickup, he visits not only major car dealerships but also every jackleg garage he happens upon in dusty sun-blasted towns of the Deep South.
noun
A type of drill operated by means of compressed air.
(US) An amateur; an untrained or incompetent person.
1999, David Horsley, Into the Wind, Houston, Texas: Winedale Publishing, “Tops for Trees,” p. 180,
If it were up to me, we’d have a city ordinance against incompetent pruning of trees. You need a permit to unclog a sewer or fix a light switch, but any jackleg with a chainsaw can climb up a ladder and undo in five minutes what Mother Nature took decades to accomplish.
(US) A shyster or con artist; a gambler who cheats; a generally dishonest or reprehensible person.