Life in Troy Grove, Illinois started to become a bore for James. He got a job as a wagon driver in Utica, Illinois. He ended up throwing his boss in the canal when he mistreated James' horse team. He moved on to Kansas with his brother in 1856 and joined an anti-slavery group called Kansas Free Starters He was also elected as Constable in 1858 of Monticello, Kansas.
In 1861 James joined the Union as a civilian scout. He fought in the Battle of Wilson Creek but the Union lost that battle. After the war ended James moved to Springfield, Missouri to look for a job. This is where he got into a gunfight with Dave Tutt. James killed Tutt and then proceed to threaten his friends. He was arrested but then set free when it was decided that he acted in self-defense.
After many years James ended up in the town deadwood playing cards with his friends. Hickok always sat with his back to the wall but after being teased about it he didn't. He still sat where the front door was in sight but his he his back was towards the back door.That's when Jack McCall walked up behind James and shot him in the back of the head. The cards that he was holding is now known as The Dead Man's Hand