Jackman was born in
Jessamine County, Kentucky, in the spring of either 1826 or 1828, the son of Thomas Jackman and his wife Mary Drake. Sometime in 1830, the family moved to
Howard County, Missouri, where Sidney Jackman was taught some basic schooling. By late in the 1840s he was living in
Boone County, Missouri, where he look up work as a schoolteacher as well as farming. On February 18, 1849, Jackman married his first wife, Martha Rachael Slavin, in Boone County, and they had two daughters and four sons together. Soon after getting married Jackman moved his family to
Howard County, Missouri, and in 1855 they settled in
Papinville, located in
Bates County. In both locales Jackman again was farming and teaching. Jackman organized local
militias while in Papinville to deal with "
Jayhawker" and other raids from nearby
Kansas, and in 1860 he relocated his family further into Missouri's interior to try to avoid these troubles. By the time of the American Civil War, Jackman was a
captain in the Missouri State Militia. ==Civil War service==