Dickie Tayloe was born in Norfolk, Virginia, in May 1942. His father was assistant director of the first housing authority in the country in Norfolk and later a member of the housing authority in Charlottesville. He recalls that Norfolk was a Navy town, “a big, rough city,” where the awful “N” word was commonly used. At the time, the more common term among his family and friends for the African American population was “colored people.” After moving to Charlottesville, he entered Lane High School a year behind and lost a second year due to the closing of the school, so he did not graduate until 1962. During his years at Lane, he did not have a Black person in any of his classes even though the school was integrated. His primary contact with African Americans was with people who worked in the neighborhood or for his family and through an afternoon job distributing the local newspaper (The Daily Progress) to the Black and White paperboys who threw the papers from their bikes to their customer’s porches or yards.
An avid sports fan, he spent free time talking with his friends about high school sports. Burley High School was his favorite. In 1956, he went to a football game at Burley, which was well-known for both their incredible football team and band. He loved the pageantry: “the place was packed… there were lines of people all the way around, …the band was unbelievably fantastic,” and “the cheerleaders and flag wavers and everything else.” Tayloe tells a story about Charlottesville Judge George Coles, who had been a high school and college football standout. Judge Coles made arrangements for the Tayloes to accompany him to watch a Burley game. As soon as the party had headed to seats on the 50-yard line, an usher approached Judge Coles and said, “You can’t sit here. The whites-only section is down on the 10-yard line.” The judge and his guests viewed the game from the 10-yard line.