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Through interviews conducted with diplomats of both Canada and Cuba, this book analyzes the evolution of bilateral relations between the countries with a focus on the last thirty years.

The relationship that Canada has with Cuba is unique. Despite historically close ties with the United States, which still maintains the "Trading with the Enemy Act" towards Cuba, Canada has consistently maintained solid diplomatic relations with the revolutionary government. Canadians make up the single largest group of tourists to the island (about 40% of those traveling there), Cuba is the largest trading partner in the region for Canada, and Canadian company Sherritt International is the second largest in the country. John M. Kirk discusses how these countries maintain a normal relationship, despite fundamental disagreements on an ideological level. This book offers a discussion on the developments during key government administrations including the governments led by Jean Chretien, Stephen Harper, and Justin Trudeau.