This collection of Ben Holladay's papers provides fragmentary documentation of his life and career. It includes letters, letterpress copybooks, court documents, genealogical materials, and a scrapbook of news clippings from 1872, primarily concerning politics. The materials relate to Holladay's personal matters; the Willamette Real Estate Company and the Oregon Real Estate Company (1870-1880); Seaside House, his home in Seaside, Oregon (1874-1876); and legal matters concerning the Oregon Central Railroad Company (1884). The letterpress copybooks include copies of letters from George Weidler, an associate of Holladay's in Portland real estate ventures, and H. Hampton, secretary of the Willamette Real Estate Company. A copybook from Seaside House includes copies of letters from Holladay's personal secretary, R. N. Fowler.