James J. "Jim Crow" Chiles (May 1, 1833, Jackson County, Missouri–September 21, 1873) was a Confederate outlaw.
The son of two-time Missouri State Senator James Chiles and the uncle of future President of the United States Harry S. Truman,[1] Chiles married Sarah Ann Young in 1859.[2]
In the American Civil War, Chiles rode with William Quantrill's gang, which included some of the most infamous raiders of the time, including Jesse and Frank James, the Younger Brothers, Ike Flannery, William "Bloody Bill" Turner. They and Chiles successfully raided many pro-union towns and caused havoc for many northern families and union supporters. One of the best known raids that Chiles can be associated with is the infamous Lawrence Massacre in August 1863. The gang killed more than 150 men and boys and burned most of the town.
Normal life was hard for Chiles after the war, so Chiles, along with many other raiders, continued his ways long after the war. Chiles went on to kill nine more men after the war, and was wanted on indictments for three other murders, up until 1873, when he was killed by a deputy marshal in Kansas City.