In fact, he was "a highly unsavory character… the dark side of frontier life, a future skeleton for the Young-Truman family closet."
Chiles and his brothers Elijah and Henry were fined in Jackson County in the 1850s for racing and gambling on Sunday.
[2] During the American Civil War, Chiles rode with William Quantrill and Bloody Bill Anderson.
[5] They and Chiles raided and burned many pro-union towns and caused havoc for many union supporters and northern families.
[3] In 1863, Chiles established a combination saloon, gambling house, and hotel in Sherman, Texas.
On September 21, 1873, he was killed by Deputy Marshal James Peacock during a confrontation in downtown Independence, Missouri.