It is around 1885 when Otto Chenoweth, a teenager from a good family with a talent for making friends and creating art, moves from refined Massachusetts to untamed Wyoming in search of beautiful scenery to paint. After Otto secures work on a cattle ranch, he meets two workers with experience on the wrong side of the law. After they convince Otto to move with them to the Sundance country, Otto's life takes a new direction as he gambles, homesteads, rustles, and occasionally gets in trouble with the law. Twenty years later, a Wyoming sheriff captures an unruly prisoner. Otto, who has just stolen a herd of over one hundred branded horses, is now known as the Gentleman Horse Thief. As the law threatens drastic control over his behavior, Otto is declared insane. After the sheriff returns him to the east in an effort to shield him from those who still want to jail him, Otto undergoes a remarkable transformation that leads him back to the west where he channels his risk-taking impulses into minerals prospecting and, in an ironic closure to his experiences with law enforcement, is elected as justice of the peace. The Lives of Otto Chenoweth shares the fascinating biography of a Wyoming horse thief who surprisingly turned over a new leaf in mid-life and dispensed justice on the good side of the law.