“The biggest challenge every Conservative leader has is figuring out how to balance the members of the Conservative Party of Canada with the kind of people they need to get to vote for the Conservative Party,” said Ken Boessenkool, a former Conservative campaign strategist from Alberta. “Those two groups of people live on different planets.”
Mr. O’Toole came to politics relatively late in life. He studied at Canada’s Royal Military College with the hope of becoming a fighter pilot but instead spent 12 years as a navigator in Canada’s then-aged fleet of ship-borne helicopters.
When Mr. O’Toole was in college, his father left a management job at General Motors’ Canadian head office east of Toronto to become a conservative member of the provincial legislature, a post he would hold for 19 years.
A door opened for Mr. O’Toole to enter politics in 2012, after he had worked for two large law firms in Toronto and later as corporate counsel at Procter & Gamble Canada. A cabinet minister resigned from the seat in the electoral district where Mr. O’Toole had grown up and had been living since he returned after studying law, in Durham, Ontario.
Mr. O’Toole, who had become active within the Conservative Party while at law school, won the special election created by the vacancy in 2012. (Mr. O’Toole still lives in the Durham region today with his wife Rebecca, a corporate affairs consultant and event planner, and their two children.)
Then in 2015, he held a cabinet position for 10 months in the government of Stephen Harper as veterans affairs minister, after the previous one was demoted after a testy exchange with veterans over service cuts and pension benefits.
In 2017, Mr. O’Toole unsuccessfully sought to replace Mr. Harper as the party’s leader, running as a moderate. Last year, he prevailed with a hard-right approach, running as a “true blue Conservative” (blue is the party’s color) who promised to “take back” Canada. Once he won, though, Mr. O’Toole repudiated much of that — launching an appeal to union members, a group rarely courted by Conservatives in the past, while making it clear that he would not reopen debate on abortion.