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Bush, John Edward (15 November 1856–11 December 1916), businessman and politician, was born a slave in Moscow, Tennessee. In 1862 his master moved him and his mother to Arkansas to keep them from being freed when the Union army moved into western Tennessee. His mother died when Bush was only seven years old. He was educated in the freedmen’s and public schools of Little Rock and was considered a good student by his teachers. He paid his school tuition by molding bricks. In 1876 he graduated from high school with honors and was immediately appointed principal of Capital Hill School, a public institution for African Americans in Little Rock. In 1878 he moved to Hot Springs, where he was named to head that city’s African-American high school....

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DeWolf, James (18 March 1764–21 December 1837), slave trader, politician, and businessman, was born in Bristol, Rhode Island. His father, Mark Anthony DeWolf, emigrated from Guadeloupe Island, West Indies, after being hired as a deckhand on a slave-trading vessel owned by Simeon Potter. Once back in Bristol, Potter introduced Mark Anthony to his sister Abigail Potter. The two married shortly thereafter and had fifteen children; eight were sons of which three died at sea. The remaining five boys, including James, became involved in the transatlantic slave trade. All the DeWolf children, boys and girls, received a formal education and lived a somewhat privileged life....

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Napier, James Carroll (09 June 1845–21 April 1940), politician, attorney, and businessman, was born on the western outskirts of Nashville, Tennessee. His parents, William C. Napier and Jane E., were slaves at the time of his birth but were freed in 1848. After manumission and a brief residency in Ohio, William Napier moved his family to Nashville, where he established a livery stable business. James attended the black elementary and secondary schools of Nashville before entering Wilberforce University (1864–1866) and Oberlin College (1866–1868), both in Ohio....

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Singleton, Benjamin (15 August 1809–1892), black nationalist and land promoter, known as “Pap,” was born into slavery in Nashville, Tennessee. Little is known about the first six decades of his life. In his old age Singleton reminisced that his master had sold him to buyers as far away as Alabama and Mississippi several times, but that each time he had escaped and returned to Nashville. Tiring of this treatment, he ran away to Windsor, Ontario, and shortly thereafter moved to Detroit. There he quietly opened a boardinghouse for escaped slaves and supported himself by scavenging. In 1865 he came home to Edgefield, Tennessee, across the Cumberland River from Nashville, and supported himself as a cabinetmaker and carpenter....