John Middleton was born in either 1854 or 1855 in Tennessee. There are many different versions of his early life, due to the fact that his name was extremely common in those days. What is known is that he first arrived in Lincoln County in 1872, possibly from Kansas, or possibly from Texas, where he killed a man in an argument. Upon his arrival in New Mexico, he worked for the Hunter & Evans cattle corporation, but later may have worked for L. G. Murphy & Co. He soon became well-known throughout the county as an excellent marksman, both with a rifle and pistol. On October 20, 1877, rancher John H. Tunstall hired Middleton as a gunman/ranch-hand. On February 18, 1878, Middleton was helping Tunstall and other ranch-hands herd nine horses from Tunstall's Rio Feliz ranch to Lincoln town when Tunstall as ambushed and murdered by gunman under the influence of Jas. J. Dolan & Co. After Tunstall's murder, Middleton joined the Regulators as a founding member, and was almost immediatly involved in the murders of William McCloskey, Billy Morton, and Frank Baker. A month later, on April 1, 1878, Middleton was one of six Regulators to ambush Sheriff William Brady and four of his deputies in the street of Lincoln. Three days later, Middleton was one of the fourteen Regulators who participated in a gunfight with Andrew "Buckshot" Roberts at Blazer's Mills. In the ensuing gunfight, Roberts was mortally wounded, Regulator leader Dick Brewer was killed, Regulators Charlie Bowdre, George Coe, Doc Scurlock, and Billy the Kid were injured, and Middleton himself was severely wounded in the chest. He was so badly wounded that he pretty much 'sat out' the rest of the fighting battles of the Lincoln County War. However, on April 18, he, along with Billy the Kid and Henry Brown, were indicted by a grand jury for the murder of Sheriff Brady. When the climatic Five-Day Battle occurred in Lincoln from July 14 to July 19, 1878, Middleton occupied the Ellis house along with Doc Scurlock, Frank Coe, Dirty Steve Stephens, and Charlie Bowdre. Early on July 19, the U.S. Army arrived and threatened to destroy the building with a howitzer, causing the Regulators occupying it to flee. Following the end of the Five-Day Battle (and the Lincoln County War as well), Middleton, along with the last remaining Regulators, Billy the Kid, Henry Brown, Tom Folliard, and Fred Waite, stole several horses from the Fritz ranch and herded them to Tascosa, Texas. After selling off the horses, Middleton, as well as Waite and Brown, elected to leave the Regulators. He then traveled north to Sun City, Kansas, where he bought a grocery store with some saved money. After the business went bust, he returned to working cattle. He somehow acquired the address of John Tunstall's father in England and began keeping a correspondence with him. In his letters, Middleton asked Tunstall senior for compensation for his services during the Lincoln County War. The elder Tunstall sent him twenty-five dollars just before Middleton was married on December 18, 1879 to Maria H. Colcord, fifteen years old at the time. Like several other Regulators, there is some confusion over Middleton's death. The most popular version is that he returned to New Mexico Territory, and died in the town of San Lorenzo of smallpox on November 19, 1882, after confessing to killing a man in Texas before coming to Lincoln in 1872. Another version is that he died in 1886 due to the old bullet in his lung that he received from Buckshot Roberts during the Lincoln County War. A third, recently proposed version, is that he lived until the 1920s.
