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" Anderson. 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 September 21, 1873, when he was killed by Deputy Marshal James Peacock during a brawl in downtown Independence, Missouri.
- Cartmell, Donald (2001) The Civil War Book of Lists
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