He had two brother who were seven and eight years older than he was, and a sister who was two years older. Whitehead was always treated by his parents as the baby of the family and, rather surprisingly, they considered him a sickly and frail child when it appears that this was not the case. Whitehead was not sent to primary school because his parents thought that he was too delicate, so he was taught at home by his father until he was 14.
Whitehead ay laging ginagamot sa pamamagitan ng kanyang mga magulang na ang sanggol ng pamilya at, sa halip kahanga-hanga, sila ay itinuturing siya ng isang mahina at marupok anak kapag ito ay lilitaw na ito ay hindi ang kaso. Whitehead ay hindi na ipinadala sa primaryang paaralan ng mga magulang dahil sa kanyang isipan na siya ay masyadong pihikan, kaya siya ay nagtuturo sa bahay sa pamamagitan ng kanyang ama hanggang siya ay 14.