Harold Callwood, Jr. was the fourth of five children of Harold Callwood, Sr. (b. 1896) and Mary Meggison (1872-1960). He married Gladys Lavoie (b. c1906) first on 26 December 1922 in a Presbyterian service, then again on 25 November 1923 in a Catholic service. On his first marriage record, he is listed as sheet-metal worker; on his second as a plumber. As early as 1926, he had taken employment in Detroit, leaving his wife and daughter Jean (1924-2007) in Belle River, ON. A second daughter, Jane, was born in 1927. Although an obituary notes that Byng "established the Superior Tinning and Retinning Company," he is registered on US travel documents as living in Belle River, but working in Detroit after April 1926. Before 1934, his business was bankrupt, and the family moved to Kitchener, ON. Byng left his family permanently in 1937, although he was in touch with them during the Second World War, when he served with the Royal Canadian Engineers.

Left motherless as a toddler, Gladys Lavoie was sent to a Convent school in Montreal after her father remarried. At the age of 16, she escaped the confines of the restrictive school by marrying Harold "Byng" Callwood (1901-1977). The couple were married twice: first on 26 December 1922 in a Protestant service, then on 25 November 1923 in a Catholic service. On both marriage certificates, Gladys lists her age as 18. They initially settled near Byng's family in Tilbury, ON, where their daughter June (1924-2007) was born in 1924. June was followed in 1925 by a son, Henry, who lived only 9 hours. In about 1926, the family moved to Belle River, ON, where Gladys's family lived, and where Gladys's father made a significant amount of money running liquor over the Detroit River into the United States. Although an obituary notes that her husband, Byng, "established the Superior Tinning and Retinning Company," he is registered on US immigration documents as living in Belle River, ON, but working in Detroit, IL, after April 1926.

Henry was born prematurely and lived only 9 and a half hours.

Trent Frayne was born 13 September 1918 in Brandon, Manitoba, only child of Homer Frayne (b. 1887) and Ella Trent (b. 1891). His celebrated career as a sports reporter spanned over 60 years, and included winning the National Newspaper Award for Sports Journalism in 1975 as well as a number of other awards. He is remembered as one of Canada's leading sport journalists, and also wrote a number of books, including an autobiography, (1990). Working at the in the 1940s, he met June Callwood, whom he married on 13 May 1944. The couple had four children: Jill, Brant, Jesse, and Casey. Trent Frayne died in Toronto on 11 February 2012.

The Frayne family seems to have been beset by ill fortune. The eldest son, Brant (b. 1948), is wheel-chair bound after a necessary brain surgery resulted in complications. The eldest daughter, Jill (b. 1945), was seriously injured when she was hit by a car while cycling. Medical experts thought she would die, or at least be paralyzed for life, but she eventually recovered completely. The youngest son, Casey (1961-1982), was killed in a motorcycle accident at the age of 20, victim of an impaired driver; his death was the impetus for Callwood's founding of Casey House, a hospice for people with HIV/AIDS. Only Jesse (b. 1951), the second daughter, seems not to have experienced a traumatic accident.

Both Jesse and Jill are authors in their own rights: Jesse has published a cookbook, (2001) as well as a novel, (2005); Jill published the autobiographical in 2002. Jesse, an author and equestrienne, has four children; Jill is a family therapist, and has one daughter.