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In 1874 Liddell was convicted of horse stealing and served three and a half years in the Missouri State Penitentiary. In 1879 he joined the Frank and Jesse James gang for their robbery of the Glendale Missouri bank. In 1881, Liddell was arrested, tried, and found guilty for the robbery of a U.S. paymaster. Released from custody, he testified against Frank James when the famous outlaw was tried in Gallatin, Missouri, for the murder of a passenger during a train robbery. Following the trial, Liddell went to New Mexico, traveled to New Jersey, and was finally arrested in Missouri in 1891 for the 1881 murder of Wood Hite, another member of the James gang and perhaps Jesse’s closest friend
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