Early Life, Education, and Career
Massey was born in Toronto, Ontario, as the son of Anna (née Vincent) and Chester Daniel Massey, the owner of the Massey-Harris Co. (predecessor company to the Massey-Ferguson Tractor Company) and the patriarch of one of the city's wealthiest families. The clan was strongly Methodist and played an important role in supporting local religious, cultural, and educational organisations, including Victoria University, Massey Hall, and the Metropolitan Methodist Church (now the Metropolitan United Church). Massey was thus raised amongst Toronto's elite, which would give him a number of social and familial connections throughout his life, as occurred with his younger brother, Raymond Massey, and his children, Anna Massey and Daniel Massey.
Massey was raised in the family's mansion at 519 Jarvis Street and educated at St. Andrew's College, in Aurora, Ontario, before enrolling in University College at the University of Toronto (UofT), despite his family's close ties to Victoria College. There, he in 1907 enlisted in The Queen's Own Rifles of Canada and joined the Kappa Alpha Society, through which he met his long-time friend and future prime minister of Canada, William Lyon Mackenzie King. After passing matriculation three years later with his Bachelor of Arts degree in history and English, Massey then went on to continue his education at Balliol College at the University of Oxford, earning his Master of Arts in history.
Feeling since his time as an undergraduate at UofT that the institution lacked a facility where its 4,000 students could engage in extracurricular activities, in 1911 Massey donated $16,290 to augment the money students had already raised for building a student centre and thereafter led the endowment and construction efforts. In 1913, he returned to Toronto and became the first Dean of Men at the Victoria University residence his father had recently donated, Burwash Hall, as well as a lecturer on modern history at the college. Then, on June 4, 1915, Massey married Alice Parkin, the daughter of Sir George Robert Parkin, who was a former principal of Upper Canada College (UCC) and secretary of the Rhodes Trust; through the marriage, Massey later became the uncle of George Grant and the great-uncle to Michael Ignatieff. But, he was not with his new bride long before, at the end of 1914, the United Kingdom, and thus Canada along with it, had declared war on Germany. Massey was commissioned as an officer for Military District No. 2 and was called to work for the Cabinet war committee before being discharged at the cessation of hostilities in 1918.
Once again a civilian, Massey started in 1921 as president of his father's business, while simultaneously pursuing philanthropic interests, mostly in arts and education, such as his collecting paintings and sculpture through his Massey Foundation, which he established in 1918. By the next year, UofT's social and athletic facility was complete and dedicated in memory of Massey's grandfather, Hart Massey, as Hart House; there, while he headed Massey-Harris Co., Massey participated as an amateur actor and director in the building's theatre. But, in 1925 he resigned from the corporate life he was unsuited for and, as a friend of Mackenzie King, by then the Prime Minister of Canada, Massey was appointed on September 16, by Governor General the Viscount Byng of Vimy, to the King's Privy Council and was subsequently made a minister without portfolio in the Cabinet. It was desired that Massey, as a minister, hold a seat in the House of Commons, yet he failed to win his riding of Durham in the 1925 federal election, held on October 29. Though he thereafter resigned his cabinet post, Massey was still included in the Canadian delegation to the 1926 Imperial Conference, where was drafted the Balfour Declaration that would ultimately lead to vast constitutional changes in the role of the monarch and his viceroys throughout the former empire.
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