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As the race for the leadership of the Conservative Party gets under way, the likely contestants fall into two categories: those who could win the party, but maybe not the country, and those who could win the country, but maybe not the party.

At this early stage, the three most likely candidates are Ontario MPs Erin O’Toole and Pierre Poilievre, and former Quebec premier Jean Charest. Let’s look at the three.

Mr. O’Toole placed a respectable third in the 2017 leadership race. He has had a life outside politics, with prior careers in the military and as a lawyer. Toward the end of Stephen Harper’s last government, he was minister of veterans affairs. He represents the riding of Durham, in the Greater Toronto Area, a region the Tories simply must do better in, if they ever want to form government again.

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Conservative MP Erin O'Toole, seen here during Question Period in the House of Commons on Nov. 26, 2018, placed a respectable third in the 2017 leadership race.

Justin Tang

Mr. O’Toole’s experience and obvious abilities would make him a formidable opponent to the Liberals. But could he win the leadership? He supports LGBTQ rights and has said his government would never legislate on abortion. He supports a robust immigration system based primarily on recruiting economic-class immigrants. He believes in the need to combat global warming (though he opposes carbon taxes).

For some Conservatives, Justin Trudeau personifies a Canada that they believe is going to the dogs – governments too large, rural areas hollowing out, traditional values under attack, too many immigrants arriving each year. They are very angry. Mr. O’Toole is not that angry.

Angry Conservatives are more likely to be attracted to Carleton MP Pierre Poilievre, who refers to Mr. Trudeau as the leader of a “corrupt Liberal cabal.” Though he is a moderate on social issues, Mr. Poilievre’s take-no-prisoners approach to politics will attract the sorts or Conservatives who detest everything about the Prime Minister, starting with his socks.

The problem is, millions of Canadian don’t detest Mr. Trudeau. They may question his judgment, his ethics, his antics overseas, but have no visceral loathing for the man, and may be put off by Mr. Poilievre’s extreme rhetoric.

Angry Conservatives are more likely to be attracted to Carleton MP Pierre Poilievre, seen here on Parliament Hill in Ottawa on Dec. 16, 2019.

Sean Kilpatrick/The Canadian Press

As things stand right now, Mr. O’Toole might stand a better chance of winning the next election than Mr. Poilievre, but Mr. Poilievre might connect better with the riled-up contingent within the Conservative base than Mr. O’Toole. And then there is Jean Charest, the obvious first choice who is also an impossible choice.

Mr. Charest is the obvious first choice if the goal of the Conservative Party is to win the next election, full stop. He would surely increase the size of the Tory caucus in Quebec. With his many years of experience in federal politics, he would also present well in urban Ontario. For the average voter who doesn’t follow politics closely, Mr. Charest would be the most credible alternative prime minister to Mr. Trudeau.

But what would the old Reform/Alliance base of the party think about such a Laurentian figure as leader of the Conservative Party of Canada? Mr. Charest is the literal personification of everything Preston Manning, Stockwell Day and, yes, Stephen Harper campaigned against: a deeply entrenched representative of the Central Canadian establishment. Tweedle Justin versus Tweedle Jean.

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Jean Charest, seen here in the halls at the Canadian Aerospace Summit in Ottawa on Nov. 13, 2019, would surely increase the size of the Tory caucus in Quebec.

Adrian Wyld/The Canadian Press

Mr. Charest could tell Westerners that he wants every bit as much autonomy for Alberta as he sought for Quebec. He will have explanations for his opposition to scrapping the gun registry, his support for closer ties to China, the investigation into the awarding of construction contracts in Quebec. But many core Conservatives in the West and in rural Ontario are going to say no to Jean Charest as Conservative leader, no matter what he says.

In the weeks ahead, Mr. Poilievre may convince Conservatives that he has grown as a politician; Mr. O’Toole may convince them that he’s angry, too; Mr. Charest may convince them that he understands this party is not the Progressive Conservative Party that he led in the 1990s.

And there will be other candidates. Sarnia-Lambton MP Marilyn Gladu intends to run. Rona Ambrose, the former interim leader, and Peter MacKay, co-founder of the Conservative Party and cabinet minister in the Harper years, could enter.

But at the moment, the most serious contenders are these three. Each of them faces different challenges. But any one of them could win.

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