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Whether Stephen Harper wins or loses on Monday, most observers believe #elxn42 will be his last campaign. Harper has served as Conservative leader for twelve years, prime minister for nine. Prior to that, he was in and out of politics as a Reform MP, leader of the Canadian Alliance, and leader of the Official Opposition.

He has had a long and storied career, which included bringing the political right back from oblivion, winning three elections back to back, and implementing fundamental changes to Canada’s economic, justice and foreign policy. It’s a legacy most politicians could only dream of. Whether you agree with where Harper has taken the country or not, there’s no question that he’s had a good ride.

In fact, many wonder why Harper chose to run again this time. With the Duffy scandal weighing on him over the past two years and a fixed election date looming on the horizon, many felt he had a perfect opportunity to step aside, renew the party with a leadership contest and pass the baton.

But most politicians find it hard to know when to quit, especially when they like the job. And nobody doubts that Harper revels in being “the man”. As Paul Wells reported in his first Harper opus, Right Side Up, the first time a reporter addressed him as “Prime Minister Stephen Harper”, he “admitted he liked the way it felt to hear it.”

Maybe that’s because most people — Harper included — never expected to hear it. Harper was considered too wonkish, while the new Conservative party struggled at first to find its place on the political landscape. In the 2004 election, the newly-minted Tories were plagued with “bozo” eruptions from candidates vowing to eliminate bilingualism and say “to heck with the courts” over decisions on social issues. The Liberals under Paul Martin won a minority.

If the Tories lose, the knives will be out for all those closely connected to Stephen Harper. If a Trudeau-Kenney contest appears to be a replay of the current election, it will hold less appeal for Conservatives already bruised by this interminable fight. If the Tories lose, the knives will be out for all those closely connected to Stephen Harper. If a Trudeau-Kenney contest appears to be a replay of the current election, it will hold less appeal for Conservatives already bruised by this interminable fight.

As the current campaign has taught us again, being underestimated can have its advantages. It helped Harper win power in 2006, just as it’s helping Liberal Leader Justin Trudeau ride high in the polls today. If Trudeau vaults from third place to government, it will be highly ironic — given that he would be walking the same underdog path Harper took when facing another tired, scandal-plagued regime that also played on fear (remember those guns-in-our-streets ads the Martin Liberals ran?) to cling to power.

So whether Harper is defeated and quits, or wins and stays on until a leadership is called, the big question for many Conservatives is: who’s next? Even before the election, heirs-apparent were dropping like flies. Cabinet ministers John Baird, Peter MacKay, James Moore, Shelley Glover and a list of lesser talents either quit or announced that they would not run again. This election, three more cabinet members are expected to go down to defeat: Chris Alexander, Julian Fantino and Joe Oliver. Pierre Polievre is being targeted as well, as is Parliamentary Secretary Paul Calandra. The talent pool is getting awfully shallow.

To be sure, there are still some bright lights bobbing in its waters — and apart from Jason Kenney, who remains the odds-on favorite for succession, they’re mostly women: Lisa Raitt, Kellie Leitch and Candice Bergen. Quebec minister Maxime Bernier probably would throw his hat into the ring. And there’s at least one outside candidate already expressing interest in the job — former Toronto councillor Doug Ford, who is helping to organize a rally for the Conservatives this weekend (to the great chagrin of many in the party).

Kenney’s roots and strength in the party are so deep, however, that it would be difficult for any other contestant to dislodge him from the pole position. In particular, Kenney has been working diligently to build relationships with ethnic communities across the country. There is a sense of mantle earned, and loyalty will be a big factor.

What’s less clear, however, is Kenney’s electability among the general population — particularly if he is seen as a direct continuation of the Harper legacy. If the Tories lose, the knives will be out for all those closely connected to Stephen Harper. If a Trudeau-Kenney contest appears to be a replay of the current election, it will hold less appeal for Conservatives already bruised by this interminable fight.

What the Conservatives need is a spirited leadership contest, but not a bloody battle. They need to go from pup tent to big tent, which requires reaching out to the voters they’ll lose to the Liberals and NDP this time around. The man or woman to do that will have a Herculean task — but it’s not impossible, particularly if the Liberals get a minority and need to tack further left to stay in power.

If the Conservatives get a minority, however, they could be facing the electorate sooner rather than later, should the other parties make good on their threat to defeat them at the first opportunity. This would throw a wrench into a leadership race — and possibly even force Harper to contest another election. Which, even for a man who enjoys the title as much as he does, seems like the last thing he’d want on his to-do list — or in the history books.

Tasha Kheiriddin is a political writer and broadcaster who frequently comments in both English and French. After practising law and a stint in the government of Mike Harris, Tasha became the Ontario director of the Canadian Taxpayers Federation and co-wrote the 2005 bestseller, Rescuing Canada’s Right: Blueprint for a Conservative Revolution. Tasha moved back to Montreal in 2006 and served as vice-president of the Montreal Economic Institute, and later director for Quebec of the Fraser Institute, while also lecturing on conservative politics at McGill University. Tasha now lives in Whitby, Ontario with her daughter Zara, born in 2009.

The views, opinions and positions expressed by all iPolitics columnists and contributors are the author’s alone. They do not inherently or expressly reflect the views, opinions and/or positions of iPolitics.