James Montgomery ( colonel ) James Montgomery ( December 22 , 1814 – December 6 , 1871 ) was a Jayhawker during the Bleeding Kansas Affair and a controversial Union colonel during the American Civil War . Montgomery was a staunch abolitionist and used extreme measures against pro - slavery populations . Early life and Bleeding Kansas . James Montgomery was born to James and Mary Baldwin Montgomery in Austinburg , Ashtabula County , Ohio , on December 22 , 1814 . He migrated to Kentucky in 1837 with his parents and eventually taught school there . He married , but his first wife died shortly after the wedding , so he married again to Clarinda Evans . They moved to Pike County , Missouri , in 1852 , and then to Jackson County and finally Bates County while awaiting the organization of Kansas for settlement . In 1854 Montgomery purchased land near present day Mound City , Kansas , where he became a leader of local Free - state men and was a fervent abolitionist . In 1857 he organized and commanded a " Self - Protective Company " , using it to order pro - slavery settlers out of the region . Conflict with other pro - slavery elements led territorial governor James W . Denver to dispatch U . S . Army soldiers in to restore order . Montgomery at times cooperated with the abolitionist John Brown and considered a raid to rescue Brown after his capture in Virginia , but snow in Pennsylvania upset his plan . Civil War . On July 24 , 1861 , Montgomery was commissioned as colonel of the 3rd Kansas Infantry of U . S . Senator James H . Lane ' s Kansas brigade , with Montgomery as second - in - command of the brigade . Discipline was lacking under Montgomery , and both the 3rd , 4th , and 5th Kansas would be consolidated into the 10th Kansas Infantry in April 1862 . Lane ' s Kansas brigade was notorious for its Jayhawker - style raids into Missouri at the start of the war , particularly the Sacking of Osceola . Noted historian Albert Castel describes Montgomery as a " a sincere , if unscrupulous , antislavery zealot . " Montgomery was authorized to raise a regiment of African - American infantry in January 1863 that would become the 2nd South Carolina ( African Descent ) . Throughout 1863 and part of 1864 , Montgomery practiced his brand of warfare in South Carolina , Georgia , and Florida . In June 1863 , Colonel Montgomery commanded a brigade , including his own 2nd South Carolina and the 3rd Rhode Island Heavy Artillery , in operations along the coast resembling his earlier Jayhawk raids . The most famous of his controversial operations was the Raid at Combahee Ferry in which 800 slaves were freed with the help of Harriett Tubman . Montgomery led a raid on the coastal town of Darien , Georgia , which he ordered looted and burned even though it was not defended and had not offered any resistance . Colonel Robert Gould Shaw , commander of the all - black 54th Massachusetts Volunteers condemned the action , and in a private letter gave Montgomery ' s reason for burning the town as " that the Southerners must be made to feel that this was a real war , and that they were to be swept away by the hand of God , like the Jews of old . " Montgomery stated to Shaw , " We are outlawed , and therefore not bound by the rules of regular warfare . " Montgomery commanded a brigade in the Battle of Olustee , where Union forces were pushed from Florida . In September 1864 he resigned his commission and returned to Kansas . He ended his military career as colonel of the 6th Kansas State Militia , active in October of that year during Confederate General Sterling Price ' s raid . Postwar . After the war , Montgomery returned to his Linn County , Kansas , farm , where he died on December 6 , 1871 .