Grayling had an elder sister Jennifer and brother John. When he was 19 years old, his elder sister Jennifer was murdered in Johannesburg. She had been born with brain damage, and after brain surgery to alleviate it at the age of 20 had experienced personality problems that led to emotional difficulties and a premature marriage. She was found dead in a river shortly after the marriage; she had been stabbed. When her parents went to identify her, her mother—already ill—had a heart attack and died. Grayling said he dealt with his grief by becoming a workaholic.