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W. Averell Harriman. Courtesy of the Library of Congress (LC-USZ62-105320 ).

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Harriman, W. Averell (15 November 1891–26 July 1986), businessman and government official, was born William Averell Harriman in New York City, the son of the railroad organizer Edward H. Harriman and Mary Averell (Mary Williamson Averell Harriman). He spent his early years in New York and on the family estate of Arden in the nearby Ramapo Mountains. He was educated at Groton and Yale. Harriman did poorly in preparatory studies, which brought admonishment from his father, and it is possible that his stammer, which he carried throughout his long life, resulted from this experience. At Yale he did better academically, and excelled socially....

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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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Plant, Henry Bradley (27 October 1819–23 June 1899), transportation executive, was born in Branford, Connecticut, the son of Anderson Plant and Betsey Bradley, farmers. His father died of typhus when Plant was only six years old, and upon his mother’s remarriage to Philemon Hoadley several years later the family relocated to Martinsburg, New York. Plant later returned to his native state and settled in New Haven, where he finished his education at a private academy. Although Plant’s grandmother offered to pay his way through Yale (hoping that he would enter the ministry), he declined the offer in favor of entering the world of work....

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Thaw, William (12 October 1818–17 August 1889), transportation executive and philanthropist, was born in Pittsburgh, Pennsylvania, the son of John Thaw, a banker, and Elizabeth Thomas. His father, after an earlier career as a merchant seaman, entered the banking business and relocated to Pittsburgh from Philadelphia in 1804. In Pittsburgh the elder Thaw served as the chief clerk in the newly established branch of the Bank of Pennsylvania. His son received his early education at local schools before entering the Western University of Pennsylvania (now the University of Pittsburgh); it is unclear whether he graduated. At the age of sixteen Thaw entered the workplace as a clerk with his father’s firm, which had since been taken over by the Bank of the United States. While employed at the bank, he traveled on horseback throughout the Ohio River valley making collections. During this trip Thaw not only gained knowledge of the area but also became aware of the tremendous potential benefits that improved transportation could bring to the region....