R.J. Bonner grew up in Ridgetown, Ontario. He graduated in classics from the University of Toronto, attended law school and was admitted to the Ontario Bar. After a brief stint as a lawyer, he turned back to classics, earning a PhD at the University of Chicago in 1904, after which he immediately joined the faculty there, eventually becoming chair of the Greek Department. His specialty was ancient Greek law. He was said to have a personality not atypical of a classics scholar: stern and demanding. He never attended graduations until after he received an honorary degree from the University of Dublin. His new red gown and hood were quite distinctive.
On December 25, 1894, R. J. married Annie Willson, a former classmate at the University of Toronto. Annie, or “Nana” as her grandchildren called her, graduated in 1890. She was the first woman to matriculate at and graduate from the University of Toronto.
R.J. and Annie had three children: Gordon Willson, Brant and later Pat, born when Annie was 42. Annie returned to Ridgetown, Ontario, to the old family Victorian farm house, for the birth of her three children even though she and R.J. were living in Chicago and had no intention of living in Canada. It was not uncommon practice in that era for women to return home to family for childbirth, where they could be assured of the support of many family members for what was then a more difficult and dangerous event than it usually is today. The farmhouse she returned to was the one built by her grandfather John Willson at Sprucehurst. In later years, Annie’s nephew John Harold Willson lived in the house until 1953, when he sold the house and land to the Province of Ontario to use as an experimental farm for the Ridgetown School of Agricultural Technology. John Harold Willson became Dean of the Agricultural School.