Oliver White was born in Richmond, Virginia, on May 1, 1907. His father, William Henry White Jr., abandoned his mother Olivia Lewis White Hill (1888–1980) shortly after the boy\'s birth, although W.H. White Jr. briefly returned six months later before leaving Richmond permanently. Though uncommon and difficult to obtain at the time, his mother thus obtained a divorce in 1911. When Oliver was 9 years old, after the deaths of his maternal grandmother and paternal grandfather, W.H. White Jr. returned briefly to Richmond and asked his son if he wanted to live with him in New York City (Oliver declined the offer).\n', '

Because Olivia Hill worked at the Homestead Resort in Hot Springs, Virginia, during the spring and fall seasons, and a related resort in Bermuda during the winter, Oliver was raised by her grandmother and grandaunt in a small house on St. James Street in a predominantly African-American section of Richmond. When Oliver was six years old, his mother Olivia Hill returned to Richmond for her mother\'s funeral, and introduced Oliver to her new husband, Joseph Cartwright Hill, who worked as a bellman at the Homestead resort. Oliver\'s maternal grandmother had moved to Scranton, Pennsylvania, but returned to Richmond shortly before her death. His paternal grandfather William Henry White Sr. had founded Mount Carmel Baptist Church in Richmond, which the family attended and where Oliver attended Sunday school, but Rev. White died on August 13, 1913, not long after grandmother Lewis. His paternal grandmother, Kate Garnet White, was reputedly part Native American, but had little to do with Oliver and his mother. Ancestors of both families had come from Chesterfield County, and at least some were likely enslaved before the American Civil War. Young Oliver got along very well with Joseph Hill, and eventually changed his birth certificate to reflect Hill\'s surname.\n', '

Joseph Hill moved his wife and Oliver to Roanoke, where he operated a pool hall until Prohibition made that uneconomic, so Joseph and soon Olivia Hill resumed their hospitality industry careers. The Hill family lived in the same house as Bradford Pentecost and his wife Lelia (d. 1943), who had no children, but often took in boarders who worked on the Norfolk and Southern Railroad like Mr. Pentecost (a cook). Hot Springs had no schools for black children, so Oliver remained in Roanoke, where he attended segregated schools until the eighth grade (the last offered to blacks in the city at the time). He also obtained his first jobs—at a local ice cream parlor (until the local police cited it for violating child labor laws), as well as delivering newspapers and ice, finding more strenuous and well-paying work as he grew stronger. During this time, the Pentecost family bought a larger house, 401 Gilmer Avenue. Hill came to consider Roanoke his childhood home. He later specifically remembered not minding serving food to strikebreakers during the Railroad Strike of 1922, because the striking unions were all-white, and sought to limit Negro employees to hard labor. Mrs. Pentecost tried to keep Oliver from working on the railroad, because her brother dropped out of college to work, and never returned, although many of her boarders were taking a year off working to pay for college.\n', '

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