James W. Jessee was born on March 8, 1838 in Empire Township, McLean County, Illinois to William J. and Nancy (Weaver) Jessee. At the age of 14 his family moved to the Kansas Territory soon after it opened up to Euro-American settlement in 1854. The Jessee family resided in Douglas County until the summer of 1857, helped founding the town of Bloomington, and returned to Illinois in the winter of 1858. William Jessee was elected as a free state delegate to the first territorial legislature, but his election was rejected with several others by the pro-slavery segment.

In July 1861 Jessee, by now a farmer, volunteered for service in the 8th Regiment Illinois Volunteer Infantry; at this same time he began keeping a diary. He served in the Civil War at various ranks, ending as a sergeant, in K Company of that regiment from July 1, 1861 to July 30, 1864. He saw action in Tennessee and Mississippi, participating in the siege and occupation of Vicksburg, Mississippi.

After mustering out in early August 1864, Jessee returned to Illinois, marrying Maria Caroline Standiford in July 1865. By 1870 he had moved his wife and twin sons Lincoln Sherman and Logan Sheridan Jessee to Kansas, settling on a farm near Olivet, Osage County, Kansas. James Wilson Jessee died on April 17, 1907 and was buried in Lebo, Coffey County, Kansas.