During the Civil War "free companies" of irregular soldiers, sometimes including renegades, bandits, bushwhackers, and partisans, infested the countryside of Indian Territory (present Oklahoma). Apologists claimed a right of retaliatory justice, whereas critics denounced guerrillas as thieves, scoundrels, ruffians, and deserters and decried their propensity for cruelty. Many were in transit elsewhere or an advance of the regular army. Some were resident or visiting families. Intratribal "blood feuds" were common. Even if the men were enrolled soldiers, ties to command structures could be tenuous. The Confederacy authorized partisans, but units varied in practice. Some acted closely with the army, and others were detached from regular service. Col. William C. Quantrill had a Confederate commission, yet his raiders were not always regarded as part of the army.
However, ambivalence existed if irregulars harassed a common foe. Some Confederates saw Quantrill as a useful officer. Others believed his band to be unmanageable and dangerous. They fought for plunder and disobeyed orders. Such "bad" men were little better than highwaymen, and some were cold-blooded killers.
Unionist empathy went to free companies that contested rebel authority, such as Pin Indians or others who took to the brush after Confederates began to treat men not registered for conscription as bushwhackers. Some marauders were Kansas "jayhawkers" or "Red Legs," notorious for plundering cattle and other property. Even pro-Union Cherokees protested against whites who were sometimes loyal, sometimes rebel, as best suited their purpose of stealing.
Irregulars often held southern sympathies. They operated in rough terrain, ambushed detachments or couriers, and sought resupply from the enemy. They fought if advantageous, or ran away. Occasionally, they deceptively wore Federal uniforms. Bands plundered homesteads and, at times, took civilian hostages. They eluded capture by escaping into the woods. A network of civilian abettors facilitated security and located markets for stolen property. Such warfare led to counterinsurgency measures. Union officials at times protected southern civilians to mollify antipathies. Eventually, though, policies became less tolerant, and loyal Indians were praised for massacring partisans. The army established an alert system and blockhouses along supply routes. Rainfall and river crossings were monitored, straggling curbed, and timetables varied for wagon trains. Rebels in Federal uniform received drumhead trials and immediate executions. Patrols grew alert if grass supplied forage, leaves gave cover, or women became insolent. To gain the element of surprise, the Union army began to pursue guerrillas to their hiding places.
Both sides appreciated the strategic value of irregulars. They conducted secret missions, disrupted communication and supply lines, captured small arms, reduced enemy ranks, made feints, and masked regulars moving into forward areas. As scouts, they garnered intelligence on supply levels and on the strength, morale, and movement of troops. Their presence required escorts for supply trains, or detachments for pursuit, thus restricting scouting in enemy territory. Irregulars at times served with regular units on cavalry raids and, on occasion, in general battle. In addition, they visited a "reign of terror" on loyal homesteads, evoked fears in Kansas of an incursion of raiders, and thereby diverted troops from duties elsewhere.
The actions of irregulars fueled debate on the righteousness of respective war efforts. Some conservative Union generals blamed outrages, in part, on radical policies that punished the innocent or licensed "jayhawker" rascality. More universally, Federal officials decried Confederate guerrillas as a disgrace to humanity. Less venom was exuded if Rebels were murdered or pillaged. But the government usually lamented atrocities Union troops committed and demanded tighter discipline. Thus, Federal leaders insisted they upheld the usages of civilized warfare. Even the policy to execute Confederates in Federal uniform was cited as a means to prevent war from degenerating into savagery.
Confederates claimed that partisans were patriots. They claimed that hypocritical Federals inaugurated "murderous and uncivilized" warfare. A Cherokee officer, for example, condoned executing enemies on retaliatory grounds. Some authorities, though, objected to white men using Indian country as a base for predatory warfare on Kansas and Missouri. Others denigrated plundering as disgraceful and tried to suppress it. One commander deemed partisan leaders responsible for murders or robberies by their men and felt it irresponsible to punish peaceful men at home for no reason other than Unionist sentiment. Even an officer in Quantrill's band came to question the custom of executing captives. He released two prisoners, wrote their leader that he regretted inhuman treatment of captives, and proposed adopting a different policy. His plea had little impact. If Federals and Confederates in the East sometimes exhibited mutual respect or empathy between battles, the "Black Flag" character of the war in Indian Territory illustrates a venomous spirit and disregard for sanctity of human life that also characterized the Civil War.
Ethelbert C. Barksdale, "Semi-Regular and Irregular Warfare in the Civil War" (Ph.D. diss., University of Texas, 1941).
Wiley Britton, The Civil War on the Border, 2 vols. (3d ed., rev.; Ottawa: Kansas Heritage Press, 1994).
Richard S. Brownlee, Gray Ghosts of the Confederacy: Guerrilla Warfare in the West, 1861–1865 (Baton Rouge: Louisiana State University Press, 1958).
Albert Castel, "Quantrill's Bushwhackers: A Case Study in Partisan Warfare," Civil War History 13 (March 1967).
LeRoy H. Fischer and Lary C. Rampp, "Quantrill's Civil War Operations in Indian Territory," The Chronicles of Oklahoma 46 (Summer 1968).
Henry E. Palmer, "The Black-Flag Character of the War on the Border," Kansas Historical Collections 9 (1905–1906).
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Tom L. Franzmann, “Free Companies,” The Encyclopedia of Oklahoma History and Culture, https://www.okhistory.org/publications/enc/entry.php?entry=FR012.
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