The following excerpt is from Freedom Fighter: John Diefenbaker’s Battle for Canadian Liberties and Independence by Bob Plamondon, published by the Aristotle Foundation for Public Policy. Foreword by Jean Chrétien. 

Senator John F. Kennedy of Massachusetts visited Canada in October 1957, four months after John Diefenbaker had become prime minister, to receive an honorary doctor of laws from the University of New Brunswick. Prematurely, but not inaccurately, Kennedy was introduced by the university chancellor as the next president of the United States. In his remarks, he dismissed Diefenbaker’s attempt to divert trade away from the United States as “deluded,” noting, “It would be a pity to rigidify the Canadian economy merely for the sake of breaking lances with a phantom American colonialism.” These were harsh words, especially for an American politician to deliver on Canadian soil and an early indication of the difficulties he would encounter with Diefenbaker in matters of state and a personal relationship.

Impertinent comments by a then U.S. senator aside, President Dwight D. Eisenhower visited Ottawa in July of 1958, addressing the Canadian Parliament and meeting Diefenbaker at the prime minister’s official residence at 24 Sussex Drive. Eisenhower’s objective was to “discourage any trend towards a narrow position of Canadian nationalism.” In his address, Eisenhower declared “that we should talk frankly to each other. Frankness, in good spirit, is a measure of friendship.” Refuting that Canada held fewer sovereign rights than the United States because of its dependence on its more powerful neighbour and ally, Eisenhower concluded, “The hallmark of freedom is the right to differ as well as the right to agree.”

Eisenhower had termed out as president, and Kennedy was sworn into office in January 1961, but Diefenbaker would have preferred Richard Nixon, Eisenhower’s vice-president, as his counterpart. In 1958, Nixon had written to the recently elected Canadian prime minister: “I, personally, could not have been more pleased that you have now earned a majority from the Canadian people.” Diefenbaker not only liked Nixon but was skeptical of Kennedy, telling his ambassador to the United States, Richard B. Wigglesworth, a few months before the 1960 American election that the silver-spooned senator from Massachusetts was not ready for the job.

In a conversation with Eisenhower, Diefenbaker suggested that Vice-President Nixon refuse a television debate with Kennedy, strategizing that “such a debate would only augment Kennedy’s stature … (that) there was no advertising value in it for Nixon.” Diefenbaker was correct, as the debate with a younger “cool” and well-tanned Kennedy ready for the television age contrasted with what the public saw of Nixon: a five-o’clock shadow, beads of sweat and eyes not accustomed to focusing on a camera and thus appeared shifty to a massive prime-time audience.

In subsequent years, Diefenbaker railed about Kennedy’s unprecedented interference in Canadian elections to ensure that a Liberal government would be installed under Lester B. Pearson, motivated primarily to rid himself of having to deal with Diefenbaker. Hypocritically, Diefenbaker had no qualms about offering advice to his Republican brethren, limited as it was in the 1960 election.

More telling of how the relationship would evolve was a gratuitous comment from Diefenbaker about the paintings he observed in the Oval Office. Of one painting from the War of 1812, depicting an American triumph over British forces, Diefenbaker commented about British victories in the seas, of which Kennedy claimed something combining ignorance and disbelief. Diefenbaker said, “I’ll show you,” referring to the encounter between the American ship Chesapeake and the British frigate Shannon on June 1, 1813. Effectively, the question of who won the War of 1812 was being relitigated in a less-than-cordial manner and in a building the British had torched.

To his aides, President Kennedy found Diefenbaker untrustworthy and told his brother, Robert Kennedy, “I don’t want to see that boring son of a b–ch again.” Robert Kennedy elaborated on his brother’s feelings about Diefenbaker much later in a conversation with Canadian journalist Knowlton Nash: “The president felt Diefenbaker was a grandstanding, insincere, sanctimonious bore. In time, he came to believe he was also a liar, a blackmailer and a betrayer.”

However, according to Lee Richardson, Diefenbaker’s executive assistant during his later years in Parliament, Diefenbaker had no personal dislike of Kennedy and enjoyed being mentioned in the same breath. He wanted to be treated as an equal and not a weak sister of a much larger neighbour. Nonetheless, that initial Washington D.C. meeting between the prime minister and the president set the tone for the executive relationship while both were in power.

Excerpt from Freedom Fighter: John Diefenbaker’s Battle for Canadian Liberties and Independence, by Bob Plamondon, published by the Aristotle Foundation for Public Policy. Reproduced with permission.