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Answer for the clue "Kansas border ruffian of the Civil War ", 9 letters:
jayhawker

Word definitions for jayhawker in dictionaries

Wikipedia Word definitions in Wikipedia
Jayhawkers is a term that came to prominence just before the American Civil War in Bleeding Kansas , where it was adopted by militant bands affiliated with the free-state cause. These bands, known as "Jayhawkers", were guerrilla fighters who often clashed ...

Douglas Harper's Etymology Dictionary Word definitions in Douglas Harper's Etymology Dictionary
American English, 1858, originally "freebooter, guerrilla, Kansas irregular" (especially one who came from the North). Hence back-formed verb jayhawk "harass" (1866).

The Collaborative International Dictionary Word definitions in The Collaborative International Dictionary
Jayhawker \Jay"hawk`er\, n. A name given to a free-booting, unenlisted, armed man or guerrilla. Note: [A term of opprobrium used in the war of 1861-65, U. S.]

Wiktionary Word definitions in Wiktionary
n. 1 An abolitionist raider in the Kansas-Missouri border skirmishes during the American Civil War 2 a robber or bandit

Usage examples of jayhawker.

When he described the time of the Border Wars, when Jayhawkers and Bushwackers raided back and forth across the border, until no place was safe from their depredations, she shook her head in sympathy.

He had heard of both jayhawkers and guerrillas operating in Louisiana, the guerrillas under the command of a man named Jarrette, a Missourian who had ridden with Quantrill and Bloody Bill Anderson.

All that mattered was that what had been done to the Missourians by the jayhawkers was being returned to the Kan-sans twice over by the bushwhackers.

He operated nominally on the Confederate side, but the Union-sympathizing Kansas Jayhawkers were just as bad.

He was the sort of man a cow outfit hired when trouble was expected from jayhawkers, homesteaders, or herd-cutters, and he was good at his job.