John H. was born 1859 in old Tishimingo County Mississippi to Richard R. Middleton/Nancy Adline Reed (Samuel B. jr./Rebecca White Reed). The family resided in old Tishimingo County until before 1880 when they appear in Scott County Ar census. Richard is buried in Starr Cem., Briartown, Muskogee, Ok. John H.'s uncle B. S. ("Doc" Benjamin S., resided in 1880 Powderly, Lamar, Tx. B. S. was paid in July/Aug 1894 acct. #8714 for 2 weeks service as a Posseman in Ok. His kids resided in Choctaw Co., Ok. after they married. B. S. son in law Thomas Briggin Bohanon (Choctaw Rolls) supposedly was some sort of lawman in Choctaw Co. Ok prior to his early death in 1913. Another son in law, John W. Threlkeld was a Deputy Sheriff in Choctaw Co Ok. Notation on photo of William C. Beeson (Nancy Middleton) states he was a Ok Federal Marshall. Beeson's resided in 1900 Earlsboro, Pottawatamie Co., Ok.

The John Middleton who ran with Billy The Kid was grandson of Drury (Drewery) Middleton shown in the 1850 census of Dallas Co. Tx. John's dad resided in several counties in Tx. Mostly in Erath/Hood counties. All these families can be found online at Rootsweb "World Connect Project".

According to Jamie Taylor, editor of the Middleton Family Journal, John Whitfield Middleton, grandson of Drewery Middleton, is not the same man who was part of the Lincoln County War. She bases her opinion due to the ages of his children's birth.