Entering Politics
He was elected mayor of the City of Guelph in 1925 after serving as an alderman. In 1929 he left to become assistant master and then master of the Supreme Court of Ontario. As a practising lawyer, in 1931, he was appointed the first Chairman of the Ontario Securities Commission by the provincial Conservative government and was fired by the Liberal government of the colourful Mitch Hepburn after it came to power as a result of the 1934 provincial election. Drew ran for the leadership of the near moribund Conservative Party of Ontario at the 1936 Conservative leadership convention losing to Earl Rowe who subsequently appointed Drew to the position of provincial organizer for the party. Drew broke with the Tories, however, when they opposed Hepburn's attempt to crush the Congress of Industrial Organizations attempt to unionize General Motors in Oshawa. He ran as an Independent Conservative in Wellington South during the 1937 provincial election but was defeated along with the Tories with Rowe failing to win a seat in the legislature and consequently resiging as party leader. Drew ran again for the Conservative leadership in 1938, this time successfully and entered the Legislative Assembly of Ontario through a 1939 by-election as the Member of Provincial Parliament for Simcoe East. In the 1943 provincial election, he was elected in the Toronto riding of High Park.
The Liberal government went through a series of crises during World War II due to Hepburn's feud with Prime Minister William Lyon Mackenzie King and the federal Liberals. These crises led to Hepburn's resignation.
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