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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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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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Arthur Sewall. [left to right] William Jennings Bryan and Arthur Sewall. Color lithograph, c. 1896. Courtesy of the Library of Congress (LC-USZC4-2130).

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Sewall, Arthur (25 November 1835–05 September 1900), shipbuilder and railroad and bank president, was born in Bath, Maine, the son of William Dunning Sewall, a shipbuilder, and Rachel Trufant. Sewall received a common school education in Bath. He was subsequently sent to Prince Edward Island to learn how to cut ship timber, and soon he was able to perform every job required in a shipyard. In 1854, during a peak period of wooden shipbuilding, he founded the firm of E. & A. Sewall with his older brother Edward and took over his father’s firm. When Edward died in 1879, the name was changed to Arthur Sewall & Co. Beginning with the 1,000-ton ...

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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....

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Cornelius Vanderbilt. Daguerreotype from the studio of Mathew B. Brady. Courtesy of the Library of Congress (LC-USZC4-4160).

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Vanderbilt, Cornelius (27 May 1794–04 January 1877), steamship and railroad promoter and financier, was born in Port Richmond, Staten Island, New York, the son of Cornelius Vanderbilt and Phebe Hand. His father, a poor farmer with nine children, increased his income with some boating around the New York harbor. In 1795 the family moved to Stapleton, on the eastern shore of Staten Island. Cornelius hated both schools and books and had no formal education past the age of eleven, when he became his father’s helper. The husky, robust boy was an expert swimmer and adept at identifying most types of sailing ships. At an early age he helped his father transfer farm produce by boat to New York City. At the age of sixteen his parents lent him $100 to purchase a small sailboat. Cornelius Vanderbilt at once set up a ferrying and freight business between Staten Island and New York City that earned more than $1,000 in the first year. The fare for the trip to New York City was eighteen cents one way or a round trip for a quarter....