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McGregor was born in Amherstburg , Canada West (now Ontario), and was educated at public schools in Windsor. He did not attend college. He moved to Manitoba in 1877, and worked in his father's cattle business in Brandon.

McGregor was one of several pioneers to the Yukon following the KlondikeThe Klondike is a region of the Yukon Territory in northwest Canada, just east of the Alaska border. It lies around the Klondike River, a small stream that enters the Yukon River from the east at Dawson. The Klondike is famed in part because of the Klondi gold strike of 1896Events January 4 Utah is admitted as the 45th U. January 5 An Austrian newspaper reports that Wilhelm Rontgen discovered a type of radiation later known as X-rays. January 12 H. Smith takes the first X-ray photograph. January 18 The X-ray machine is exhib, and served as Mine Inspector of the Yukon Territory from 1897Events January 1 Brooklyn, New York merges with New York City. January 4 A British force is ambushed by Chief Ologbosheri, son-in-law of the Oba of Benin. This leads to a Punitive Expedition against Benin. February 2 The Pennsylvania state capitol is dest to 1899Events January events January 1 End of Spanish rule in Cuba. January 1 Queens and Staten Island merge with New York City. January 3 The first known use of the word " automobile", in an editorial in the New York Times''. January 6 Lord Curzon becomes a vic. He subsequently bought a ranch near Medicine HatMedicine Hat is a city of about 50,000 people located in the southeastern part of the province of Alberta, Canada on the Trans-Canada Highway Number 1 and on the South Saskatchewan River. Nearby towns considered part of the Medicine Hat area include Dunmo (now in AlbertaAlberta is one of Canada's provinces. Its capital is the city of Edmonton. Other cities and towns include Banff, Calgary, Red Deer, Lethbridge and Medicine Hat. See also: List of communities in Alberta. As of 2004, the population of the province was 3,183), and owned 200,000 acres (800 km²) with 10,000 head of cattle and 2,000 horses.

McGregor gained international fame for his pioneering efforts in stock breeding. He was the first farmer to cultivate alfalfa in the western provinces, thereby reducing the region's dependency on the wheat market. He also founded the Glencarnock stock farms of western Canada, and won a number of international livestock prizes.

McGregor never actually ran for public office, despite repeated entreaties. In 1915Events January 12 The Rocky Mountain National Park is established by an act of Congress. January 12 United States House of Representatives rejects proposal to give women the right to vote. January 13 An earthquake (6. 8 in Richter scale) in Avezzano, Ital, he declined an appointment as Minister of Agriculture in Manitoba. Two years later, he was apponted wartime leader of the Food Control Board in the western provinces, holding the position for a year.

When Theodore Arthur BurrowsTheodore Arthur Burrows ( August 15, 1857- January 18, 1929) was a politician and office-holder in Manitoba, Canada. He served as Lieutenant-Governor of the province from October 6, 1926 until his death. Burrows was born in Ottawa, Canada West (now Ontari died in 1929, McGregor was called to succeed him as Manitoba's Lieutenant-Governor (a largely ceremonial position, though McGregor was significant in being the first non-politician to be so appointed). He held this position for five years, and died shortly thereafter.