Thompson was born in Toronto. He designed courses from 1912-1952, mostly in Canada, with a philosophy of preserving the natural lay and flow of the land. He got his start with George Cumming, longtime professional at the Toronto Golf Club, who had designed several Canadian courses around the turn of the 20th century. Thompson's many world-famous courses include the Banff Springs Hotel Golf Course in Banff, Alberta, the Jasper Park Golf Course in Jasper, Alberta, and the Highlands Links in Ingonish, Nova Scotia, all three which are publicly accessible and located in Canadian National Parks. Three outstanding private clubs designed by Thompson are the Capilano Golf and Country Club in West Vancouver, British Columbia, the Royal Mayfair Golf Club in Edmonton, Alberta, and the St. George's Golf and Country Club in Toronto. In 1946, Thompson was a co-founder, with Donald Ross, of the American Society of Golf Course Architects (ASGCA), and helped to train many top golf course architects, including Robert Trent Jones. Thompson was an excellent player himself, and he had four brothers, all of whom became outstanding Canadian players in the 1920s.