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Ben Holladay (1819-1887) was a flamboyant financier, railroad promoter, and real estate developer who was influential in Oregon during the 1870s. He was born in Kentucky and moved to Missouri with his parents. He ran successful businesses in Weston, Missouri, and made a great deal of money selling supplies to the U.S. government during the Mexican War. Moving to California in 1852, he ran successful stage coach businesses, which he eventually sold to Wells, Fargo, for a large fortune. In 1868 he came to Oregon and began promoting railroad ventures and real estate, eventually building a rail line from Portland to Roseburg, called the Oregon and California Railroad and later the Oregon Central Railroad. But with the panic of 1873 he suffered financial losses, and control of the Oregon Central passed to German bondholders, and later Henry Villard. In his heyday, Holladay lived a lavish lifestyle and owned many homes, including mansions in Washington, D.C., and San Francisco, and an elaborate villa on the Oregon coast called Seaside House. He used his wealth to finance a bid for the U.S. Senate, but he failed to win election.

Holladay was married twice, first to Notley Ann Calvert, who died in 1873, then to Esther Campbell in 1874. His two daughters from his first marriage married European aristocrats. His later years were marred by poor health, financial losses, legal difficulties, and the deaths of his two daughters. He died in Portland in 1887 at the age of 68, after a long illness.