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Cheney, Benjamin Pierce (12 August 1815–23 July 1895), transportation executive, was born in Hillsborough, New Hampshire, the son of Jesse Cheney, a blacksmith, and Alice Steele. Born into an impoverished family, he attended local common schools until the age of ten and then went to work in his father’s shop. After nearly two years working with his father, he relocated to Francistown, New Hampshire, where he took a job in a tavern and later worked in a local store....

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Holladay, Ben (14 October 1819–08 July 1887), transportation magnate, was born in Nicholas County, Kentucky, the son of William Holladay and Margaret Hughes, farmers. At age seventeen, with little education or experience beyond that gained as the son of poor farmers on the Kentucky frontier, Holladay left home, sensing opportunity lying to the west. He moved to Weston, on the Missouri-Kansas border, where he began working as a courier for militia fighting against the Mormons in the town of Far West, Missouri. In this role of ferrying messages back and forth between the Mormons and the militia, Holladay was able to gain the Mormons’ trust. After this experience, in 1838 Holladay decided to settle in Weston and made a series of entrepreneurial investments, first as a saloonkeeper and then as a druggist and dry-goods merchant. Eventually he opened a hotel and was appointed local postmaster. With his profits, he purchased his first set of freight wagons, fitting them with the extra-wide tires that would become his trademark. In 1840 Holladay met and married Notley Ann Calvert, daughter of a well-to-do Weston family; they had seven children, one of whom died in infancy....

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Reeside, James (1789?–03 September 1842), mail contractor and stagecoach proprietor, was born in Scotland, the son of Edward Reeside and Janet Alexander. His parents moved to Baltimore County, Maryland, shortly after his birth. Because the family had limited financial resources, Reeside received little formal schooling. In 1816 he married Mary Weis, and they had one son and two daughters....