W.T. (Tom) Easterbrook graduated from the University of Manitoba in 1933, the same year as McLuhan. He then went on to graduate school at UT in political economics where he obtained his MA in 1935 and his PhD in 1938.  He began teaching at Brandon that same year. In 1941, he was awarded a Guggenheim fellowship and spent the year of 1942 studying, presumably at UT. In 1943 he came back to Manitoba, but not to Brandon College — he taught at the University of Manitoba until 1946.

In 1947 he returned to UT where he eventually became the head of the political economy department like his teacher, thesis adviser, colleague and friend, Harold Innis.

In 1941 his career to that point was recorded in the Guggenheim Foundation’s Report for 1941–42 as follows:

Appointed from Canada:
EASTERBROOK, WILLIAM THOMAS:  Appointed for studies in the economic history of the Pacific Northwest; tenure, twelve months from July 1, 1941.
Born December 4, 1907, at Winnipeg, Canada.  Education:  University of Manitoba, B.A., 1933; University of Toronto, M.A., 1935, Ph.D., 1938 (Royal Bank Economics Fellow, 1933–34; Alexander Mackenzie Fellow, 1934–35; Maurice Cody Fellow, 1935–36); Harvard University, 1936–37 (Harvard University Fellow).
Assistant in Economics, 1937–38, University of Toronto.
Lecturer in Economics, 1938–40, Assistant Professor, 1940—, Brandon College of the University of Manitoba.
Publications:  Farm Credit in Canada¹, 1938.
Articles in Canadian Journal of Economics and Political Science, Encyclopedia of Canada.

In the decade between his graduate work at UT and the beginning of his teaching career there, Easterbrook returned as a visiting lecturer for a year in the early 1940’s in connection with his Guggenheim:

Innis supported [Henry] Cody‘s² program of developing graduate studies at Toronto with a proposal of his own. He was anxious to bring young professors in the social sciences from other Canadian universities to Toronto on one- or two-year stints. He argued that many of them had been struggling during the Depression with large classes and low salaries. They would benefit by a “relaxed” period (with a light teaching load) at Toronto. After becoming familiar with the Toronto system, they would return home and organize their classes along the lines of Toronto’s, using the same textbooks. In due course they would be sending graduate students to Toronto. Cody approved of the proposal and the result was a series of visits from young professors from western universities: W.T. Easterbrook (…) and others. (Donald Campbell Masters, Henry John Cody: An Outstanding Life, 1995, 208)