Of the many photographs reputed to depict Jesse James, only a handful are universally accepted as authentic. This image is one of them, capturing the distinctive clearness of his blue eyes and the slight upturn of his nose that witnesses often described. Though he appears clean-shaven here, he was usually described during robberies as wearing full, sandy whiskers. As befitting the son of a prosperous slave-owning preacher, he routinely wore fine clothes, on one occasion forced a well-dressed victim to hand over his garments.

At the time of this photograph, Jesse James was probably residing in the vicinity of Nashville. Though he frequently visited Kentucky, where he had many friends and relatives (and took part in various robberies), he spent most of his life in the neighborhood of his mother's farm in Clay County. After the Pinkerton raid in 1875, however, it appears that he and his wife Zee relocated to Nashville, perhaps to spare his mother further harrassment. There he passed himself off as an itinerant grain merchant, threw his money away at gambling on cards and horses, and wrote letters to the local newspapers to establish himself as a hero of the South. He remained a resident of Tennessee until shortly before his death, when he and his family returned to western Missouri.