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True stories from the wild and woolly west. Also really lame jokes! Each episode I cover a real life person or event from the wild west era (gunfighters, outlaws, lawmen, Native Americans, frontiersmen, etc). I'm neither a historian nor a comedian, just a fan of history. I do, however, try to be as accurate as possible when covering these topics. All whilst dispensing dad jokes and totally butchering the English language.

May 3, 2023

You can pick your friends and you can pick your nose, but you can’t pick your family. An old adage that the 33rd President of the United States Harry S. Truman knew all too well. Every family has that one black sheep, right? In the case of the Trumans, that shameful distinction fell on James John Chiles, aka Jim Crow Chiles, Harry’s Uncle by marriage; a violent Missouri Bushwhacker who fought alongside Bloody Bill Anderson and Jesse James described by author David G. McCullough as universally hated and the stuff of children’s nightmares. And believe it or not, Chiles got the nickname Jim Crow due to his talent as a dancer. Minstrel dancing, to be precise. 

Apparently in the 1830s and 1840’s there was a popular white entertainer by the name of Thomas Dartmouth Rice who performed a song-and-dance routine in blackface while mimicking African Americans. The persona he put on during his act was known as Jim Crow. Rice went on tours all over the country, even in England, and it wasn’t long before “Jim Crow” was just a common phrase used to describe all white comedians who did these degrading black-face type performances. And of course, years later the term would be adopted as the identifier for laws reinstating white supremacy in the South.

And evidently, Truman’s uncle was one hell of a Jim Crow dancer. Not exactly the type of association you’d want to have as a politician, right? Even in 1945 when Truman was elected. Oh, and don’t worry – it gets much worse. Uncle Chile’s comedy routine was the least of the future President’s worries.

Who was Jim Crow Chiles? A true menace to society or just a poor misunderstood soul just dancing away his sorrows? How did he fall in with Bloody Bill Anderson and William Quantrill? And did he really serve with General Shelby’s Iron Brigade?


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Book Recommendations!


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