He attended Upper Canada College for high school and moved on to the University of Toronto, where he received a Bachelor of Arts.

When Ferguson stepped down in 1930, barely a year into the Great Depression, Henry succeeded him as Conservative Party leader and as Premier of Ontario.

Construction of Canada's first four-lane controlled access superhighway, the Toronto to Niagara Falls Queen Elizabeth Way, was the most lasting achievement of the highway program.

Aside from building roads, his government did little to alleviate public suffering during the Great Depression, such as unemployment in the cities, or the collapse of prices for farm products in the country.

Some felt that the government had little to offer beyond more road construction, and the Tories were soundly defeated by the Ontario Liberal Party, led by Mitchell Hepburn.

[2] In 1898, Henry bought the farm house and property in which he would spend almost all of his adult life after he had graduated from the Ontario Agricultural College.