Thomas Gentleman, born in 1862, was the fourth of six children to Robert William Gentleman, Sr. and Ellen (Driscoll) Gentleman. In 1873, his family relocated to Platte Center, Nebraska, where he spent his formative years on the family farm. Between 1892 and 1897, Gentleman served as a Platte County Deputy Sheriff under D.C. Kavanaugh, who was married to his cousin, Bridget. Following this role, he became a policeman in Columbus, Nebraska. In 1898, Gentleman joined the Union Pacific Railroad as a
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