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In 1858 Hickok was elected as a constable in Monticello Township Kansas. In 1859 he joined the Russell, Waddell and Majors freight company called the Pony Express.
In 1861 he was involved in the McCanles Gang shootout where Hickok was accredited with a 75 yard off hand shot with a handgun killing David McCanles.
At the start of the Civil War in April 1861, at age 34, Hickok signed on as a Teamster and later became a Wagon Master for the Union Army in Missouri. Hickok was discharged in 1862 and does not resurface until late 1863 then as a member of the Springfield Missouri police. It is thought that during the missing year Hickok worked undercover scouting and spying in the South for the Union Army.
From 1864 to 1865 Hickok was hired as an Army Scout and worked for General John B. Sanborn. Then in 1865 Hickok had the famous long range, quick draw duel killing David Tutt, an ex-Confederate soldier.
Later on in 1865 Hickok is elected City Marshall of Springfield then appointed to the position of Deputy United States Marshal at Fort Riley Kansas, where he served occasional as a Scout for General George Armstrong Custer’s 7th Cavalry.
Hickok again in 1867 began scouting for the Army near Fort Harker and involved in several clashes with Indians.
In 1868, Hickok while serving as a Deputy U.S. Marshal in Hays, Kansas scouted for the 10th Cavalry, the famous African-American Buffalo Soldiers, where he was wounded during a rescue of some ranchers hear Bijou Creek Basin . Hickok was also reported to have tracked down and recovered Army deserters. In 1869 Hickok was elected City Marshal of Hays and Sheriff of Ellis County, however there were some election irregularities and Hickok lost the Sheriff position. Hickok killed two men during in Hays further cementing his reputation as a gunfighter.
In 1870, also in Hays, Hickok was involved in a gunfight with disorderly soldiers from the 7th Cavalry, killing one and wounding the other.
In 1871 Hickok became Marshal of Abilene, Kansas where he met and befriended noted gunfighter John Wesley Hardin. Hickok killed Phil Coe in a gunfight with resulted in Hickok also accidentally killing his deputy Mike Williams.
In 1873, Hickok joined William “Buffalo Bill” Cody in the famous stage play “Scouts of the Plains” but eventually left before Buffalo Bill established his Wild West Show.
In 1876, Hickok was diagnosed with glaucoma and possibly other vision disorders. Later on this year he married Agnes Thatcher Lake , some 10 years his elder, in Cheyenne Wyoming . Martha Jane Cannary (Calamity Jane) was known to claim that she was married to Hickok but divorced him so he could marry Agnes Lake.
Wild Bill reportedly had a premonition that he would die in Deadwood, South Dakota . He was right; he would never leave Deadwood alive as on 2 August, 1876, just 5 weeks after the Custer Massacre, he was shot in the back of the head by John “Jack” McCall while he was playing poker in Nuttal & Mann’s Saloon. When he was shot, Hickok was holding 5 cards: a pair of Aces, a pair of eights, and an unknown 5th card – this has become widely known as the “Dead Man’s Hand”.
