Ruth Barrow returned to Barbados to raise her five children with the help of her extended family, living with their grandmother Catherine O’Neal in Bridgetown. Her older brother, Dr. Charles Duncan O’Neal, was a prominent physician and activist (later a National Hero of Barbados) who founded the Democratic League and Workingmen's Association, the first socialist organization in Barbados. Under his fatherly influence, Dr. O'Neal's philosophies formed the core of the young Errol's political and social beliefs. Among Errol's playmates at his grandmother's house on Crumpton Street was his cousin Hugh Springer, later Sir Hugh, Governor General of Barbados and the third member of the family to be named a National Hero.