Bushwhacker Bushwhacking was a form of guerrilla warfare common during the American Revolutionary War , American Civil War and other conflicts in which there were large areas of contested land and few governmental resources to control these tracts . This was particularly prevalent in rural area s during the Civil War where there were sharp divisions between those favoring the Union and Confederacy in the conflict . The perpetrator s of the attacks were called bushwhackers . Bushwhackers were generally part of the irregular military forces on both sides . While bushwhackers conducted a few well - organized raids in which they burned cities , most of the attacks involved ambushes of individuals or families in rural areas . In areas affected by bushwhacking the actions were particularly insidious since it amounted to a fight of neighbor against neighbor . Since the attacks were non - uniformed , the government response was complicated by trying to decide whether they were legitimate military attacks or criminal actions . Union and Confederate bushwhackers . The term was widely used during the conflict , though it came to be particularly associated with the Confederate guerrillas of Missouri , where such warfare was most intense . Guerrilla warfare also wracked Kentucky , Tennessee , northern Georgia , Arkansas , and northern Virginia , among other locations . Two bands operated in California in 1864 . Pro - Union guerilla fighters in Kansas were called " jayhawkers " . They used tactics similar to the Confederate bushwhackers . A typical jayhawker action was a cross - border raid into Missouri . In some areas , particularly the Appalachian regions of Tennessee and North Carolina , the term " bushwhackers " was used for Union partisans who attacked Confederate forces . This term was also used by residents of southern Alabama , for the same reason . Partisan rangers . In most areas , irregular warfare operated as an adjunct to conventional military operations . The most famous such " partisan ranger " ( to use the title adopted by the Confederate government in formally authorizing such insurgents ) was Col . John Singleton Mosby , who carried out raids on Union forces in the Shenandoah Valley and northern Virginia . Partisan rangers were also authorized in Arkansas . In Missouri , however , secessionist bushwhackers operated outside of the Confederate chain of command . On occasion , a prominent bushwhacker chieftain might receive formal Confederate rank ( notably William Clarke Quantrill ) , or receive written orders from a Confederate general ( as " Bloody Bill " Anderson did in October 1864 during a large - scale Confederate incursion into Missouri , or as when Joseph C . Porter was authorized by Gen . Sterling Price to recruit in northeast Missouri ) . Missouri guerrillas frequently assisted Confederate recruiters in Union - held territory . For the most part , however , Missouri ' s bushwhacker squads were self - organized groups of young men , predominantly from the slave - holding counties along the Missouri and Mississippi rivers , who took it upon themselves to attack Federal forces and their Unionist neighbors , both in Kansas and Missouri , the latter in response to what they considered a Federal invasion of their home state . Jesse James . The guerrilla conflict in Missouri was , in many respects , a civil war within the Civil War . One of the most famous men who fought as a bushwhacker was Jesse James , who began to fight in 1864 . During months of often intense combat , he only battled fellow Missourians , ranging from Missouri regiments of U . S . Volunteer troops to state militia to unarmed Unionist civilians . The single confirmed instance of his exchanging fire with Federal troops from another state occurred a month after the 1865 surrender of Confederate General Robert E . Lee , during a near - fatal encounter with Wisconsin cavalrymen . In the course of the war , his mother and sister were arrested , his stepfather tortured , and his family banished temporarily from Missouri by state militiamen — all Unionist Missourians . Atrocities . The conflict with Confederate bushwhackers everywhere rapidly escalated into a succession of atrocities committed by both sides . Union troops often executed or tortured suspects without trial and burned the homes of suspected guerrillas and those suspected of aiding or harboring them . Where credentials were suspect , the accused bushwhacker was often executed , as in the case of Lt . Col . Frisby McCullough after the Battle of Kirksville . Bushwhackers frequently went house to house , executing Unionist farmers . One of the most vicious actions during the Civil War by the bushwhackers was the Lawrence Massacre . William Quantrill led a raid in August 1863 on Lawrence , Kansas , burning the town and murdering some 150 men and boys in Lawrence . The raiders justified the raid in retaliation for the Sacking of Osceola , Missouri two years earlier ( in which the town was set aflame and at least nine men killed ) and for the deaths of five female relatives of bushwhackers killed in the collapse of a Kansas City , Missouri jail . Following the Lawrence raid , the Union district commander , Thomas Ewing , Jr . , ordered the total depopulation ( both Unionists and Southern sympathizers and everyone else ) of three and a half Missouri counties along the Kansas border from Kansas City , Missouri south , under his General Order No . 11 . ( The Missouri - Kansas border conflict was in many ways a continuation of Bleeding Kansas violence . ) In other areas , individual families ( including that of Jesse and Frank James and the grandparents and mother of future President Harry Truman ) were banished from Missouri . Next to the attack on Lawrence , the most notorious atrocity by Confederate bushwhackers was the murder of 22 unarmed Union soldiers pulled from a train in the Centralia Massacre in retaliation for the earlier execution of a number of Anderson ' s own men . In an ambush of pursuing Union forces shortly thereafter , the bushwhackers killed well over 100 Federal troops . In October 1864 , " Bloody Bill " Anderson was tricked into an ambush and killed by state militiamen under the command of Col . Samuel P . Cox . Anderson ' s body was displayed and his head was severed . Postwar banditry . After the end of the war , the survivors of Anderson ' s band ( including the James brothers ) remained together under the leadership of Archie Clement , one of Anderson ' s lieutenants , and began a series of armed robberies in February 1866 . This group became known as the James - Younger Gang , after the death or capture of the older outlaws ( including Clement ) and the addition of former bushwhacker Cole Younger and his brothers . In December 1869 , Jesse James became the most famous of this group when he emerged as the prime suspect in the robbery of the Daviess County Savings Association in Gallatin , Missouri , and the murder of the cashier , John W . Sheets . During Jesse ' s flight from the scene , he declared that he had killed Samuel P . Cox and had taken revenge for Anderson ' s death . ( Cox lived in Gallatin , and the killer apparently mistook Sheets for the former militia officer . ) Throughout Jesse James ' criminal career , he often wrote to the newspapers with pride of his role as a bushwhacker , rallying the support of former Confederates and other Missourians who were harmed by Federal authorities during the Civil War and Reconstruction . After the end of the war in 1865 , the Mason Henry Gang continued as outlaws in Southern California with a price on their heads for the November 1864 " Copperhead Murders " of three men they believed to be Republicans , in the San Joaquin Valley . Tom McCauley , known as James or Jim Henry , was killed in a shootout with a posse from San Bernardino on September 14 of that year , in San Jacinto Canyon , in what was then San Diego County . John Mason was killed by a fellow gang member for the reward in April 1866 near Fort Tejon in Kern County . In 1867 , near Nevada , Missouri , a band of bushwhackers shot and killed Sheriff Joseph Bailey , a former Union brigadier general , who was attempting to arrest them . Among those suspected of his killing was William McWaters , who once rode with Anderson and Quantrill .