Roland’s Olive Diefenbaker lived a very interesting life being the wife of John Diefenbaker, who served as Canada’s 13th prime minister from 1957 to 1963.
Olive Evangeline Freeman was born in Roland on April 14, 1902 to Dr. Reverend David Freeman and Angie Alicia (nee Eaton). Her family had relocated from Nova Scotia and she was one of five children.
Both of Olive’s parents were of United Empire Loyalist stock. She could trace her ancestry back to Massachusetts and the pilgrims who had landed at Plymouth Rock on the Mayflower.
The Reverend Freeman, a Baptist minister, served at various churches in western Canada. As a result, the family relocated numerous times – from Roland, where she spent her early years, to Moose Jaw, Prince Albert, and Saskatoon. In 1921, she was back in Manitoba when she moved to Brandon where she graduated from Brandon College in 1923.
In 1917, a young Olive Freeman crossed paths with John Diefenbaker in Saskatoon. It was at a church where her father was employed, and Diefenbaker had recently returned from serving in the First World War. At the time, he was pursuing law studies. Olive was only 15 years old, and he was 22, so there was no instant romance. Their eventual marriage would not even be a first for either of them.
Freeman and Diefenbaker were both widowed when they reconnected again later in life.
In the early 1950s, they met and after a short courtship, Diefenbaker asked for her hand in marriage in Paddockwood, Saskatchewan. Their wedding took place in 1953. While they did not have any biological children, they did raise her daughter from a prior marriage.
Prior to her marriage to Diefenbaker, Olive had been outspoken on such topics as education and women’s suffrage, and she was a staunch supporter of the monarchy.Â
In 1964, she addressed a gathering of 600 members of the Progressive Conservative Women’s Association, emphasizing the strength and importance of women in politics. Fluent in both French and English, she displayed a preference for her French grammar over her English skills, often choosing to speak to French-speaking voters in their native language. She was a very talented conversationalist.
After Diefenbaker took office as prime minister, Olive started hosting tea for the wives of MPs. This tradition took place at the official residence for Canada’s prime minister, located on 24 Sussex Drive in Ottawa. Some notable guests included British Prime Minister Winston Churchill and American President Dwight Eisenhower.
She also assisted with the writing of Diefenbaker’s speeches and often travelled with him when he was on the campaign trail. John considered Olive an asset to his campaign team because of her ability with the voters and remembering names. She would write her husband notes during his speeches with advice on how to appeal to the voters.
For example, in 1963, while John was delivering a speech in Cape Breton, Nova Scotia, Olive wrote him a note to mention the painting they had hung over their fireplace back at home, which is a landscape of Cape Breton, to help appeal to his audience.
Together, the pair made a formidable team, with Diefenbaker widely recognized as one of Canada’s greatest prime ministers of the 20th century.
In 1975, Olive suffered a stroke and in the following year, she was hospitalized for heart disease. Sadly, she passed away on Dec. 22, 1976 at the age of 74. John Diefenbaker passed away a few years later in 1979. The pair are interred together in Saskatoon.
