Who will it be? The establishment choice, the fresh outsider or the maverick insurgent?

Caroline Mulroney is the outsider. Her family has a long history in Canadian conservatism her father was prime minister from 1984 to 1993, she is new to active involvement in the PC Party. This Leadership campaign will be her first electoral test.

Elliott’s road to the party leadership is the one most candidates take. Both Mulroney and Ford are also treading paths well-worn by outsider and insurgent candidacies in the past some of them successful, others less so.

That’s the decision members of the Ontario Progressive Conservative Party face on March 10 a choice between three very different registered candidates for the party’s leadership.

Kevin O’Leary famously quit the Conservative leadership race after becoming its front-runner. A victory for O’Leary was still plausible when he withdrew, but the businessman and TV personality who had no prior experience with the Conservative party apparently found politics to be more challenging than he expected when he was watching it from the outside.

Even recognizable outsiders can have a tough time once they step into the ring.

Christine Elliott is the experienced establishment candidate. Before stepping out of politics in 2015 following her failed leadership bid in 2015, Elliott had been an MPP for almost a decade. This Leadership Campaign is her third.

Doug Ford is the insurgent. Railing against the “elites” in both the premier’s office and the PC party leadership, Ford is hoping to tap into populist anger within the party membership and recruit supporters of the so-called “Ford Nation.”

Outsiders aplenty, but having a name helps
It is common for leadership races to feature a few contestants who emerge out of political obscurity and fail to make any headway. It’s less common for one of those contestants to have the name recognition of a Mulroney.

Being an outsider, however, isn’t always an obstacle. Wade MacLauchlan was an apolitical president of the University of Prince Edward Island when he was drafted to become premier in 2015.

In New Brunswick, Bernard Lord and Brian Gallant each had only a failed run for a provincial seat under their belts when they took over the PC and Liberal parties, respectively, and in short order became premiers.

Belinda Stronach stuck it out to the end of the 2004 federal Conservative leadership campaign, losing to Stephen Harper.

And Michael Ignatieff, who, according to his memoirs, went from not seriously considering a political run to mounting a bid for the federal Liberal party leadership in a mere 18 months– was unable to win on his first attempt, was acclaimed to the leadership on his second try and in 2011 led the Liberals to their worst electoral result in party history.

Mulroney’s biggest advantage may be that she combines the qualities of both an outsider and an insider. While a relative newcomer to the Ontario PCs, her family history gives her credibility within the conservative movement. In a short leadership campaign, getting people to pay attention and take you seriously is half the battle.

Insurgencies can take time

Getting attention is not a problem for Ford — as is often the case for insurgent candidates who run against a party’s establishment and political orthodoxy.

As with outsiders, it’s not uncommon for insurgent leadership candidates to find that the hurdles put up by the party are too difficult to overcome. Pat Stogran’s short-lived NDP leadership campaign in 2017, during which the former veterans ombudsman criticized what he called “politics incorporated,” is one recent example.

Other insurgents simply fail to sell their message. After campaigning against “elites” and in favour of screening immigrants for their embrace of “Canadian values,” Kellie Leitch finished sixth in the 2017 Conservative leadership race. David Orchard failed twice to engineer a takeover of the federal PCs in 1998 and 2003 — campaigns which saw him stand opposed to some of the party’s signature policies.

Candidates from the socialist wing of the NDP have failed repeatedly to dislodge more moderate candidates in federal party leadership campaigns.

But insurgents do not need to attain power in order to have a profound influence on a party.

At the helm of the populist Reform Party of Canada, Preston Manning was able to help engineer the collapse of the federal PCs in 1993. Though he was out of politics by the time Reform’s successor, the Canadian Alliance, merged with the PCs in 2003, he had a significant impact on what the modern Conservative party has become.

In the United States, Barry Goldwater’s brand of conservatism transformed the Republican Party and laid the groundwork for the election of Ronald Reagan in 1980. But it took Goldwater’s landslide loss to Lyndon Johnson in 1964 for that transformation to happen.

On the other hand, there’s the successful example of U.S. President Donald Trump, an insurgent (and outsider) who defeated a series of Republican establishment candidates in the 2016 primaries and then won the presidency. His impact on the future of the Republican Party has yet to be determined.

Ford’s leadership campaign comes at a time when the Ontario PC membership is in open revolt — between those who wanted a leadership race and those who didn’t; between those who owe their jobs to former leader Patrick Brown and those who don’t; and between the members who supported winning and losing candidates in contested nomination battles across the province.

Ford might find himself at home in such an environment.

Letting the people, not the party, decide

Outsider and insurgent candidacies might be more viable today than ever before. Over the last 20 years, parties have increasingly moved away from delegated conventions. This has given candidates the opportunity to mount leadership bids that don’t require the acquiescence of the party establishment. If they can sign up enough members, they can take over a party.

That’s how Jagmeet Singh, an Ontario MPP little known at the national level and with shallow networks within the federal NDP, orchestrated his victory last year.

It’s also how Brown, a low-profile backbench federal MP with thin support from the provincial caucus, managed to win the last Ontario PC leadership campaign in 2015.

But the month-long PC leadership race this year — only a few days remain for candidates to sign up members — gives little time to sign up new members attracted by an outsider, or for an insurgent to swamp the ranks of the established party base. Instead, the decision will be made largely by those pre-existing members.

Their choice won’t simply affect the party’s chances in the upcoming provincial election. It could also have a significant influence on the direction of the party for years to come.