Within hours of Doug Ford’s leadership victory last weekend, Ontario Progressive Conservatives who to that point wondered aloud whether they could possibly serve under such a person started falling into line.

Loyalty, self-preservation, opportunism, blind partisanship, genuine resolve to defeat Kathleen Wynne – whatever it was, even though only two PC MPPs had backed Mr. Ford’s campaign for Patrick Brown’s old job, others promptly began appearing alongside him at public events or enthusiastically praising him on social media.

Open this photo in gallery Doug Ford is the new leader of the Ontario PC Party. Fred Lum





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No incoming leader would think twice before accepting caucus support. But for Mr. Ford, a different sort of help that also quickly became available poses a tougher question: What to do about the backroom veterans, establishment members of a party he not long ago pronounced needed an “enema,” now making it known they too are ready to serve?

The implicit offer is that he could have something approaching a traditional campaign, steered by the same sorts of political professionals who would have done so for Mr. Brown, or Christine Elliott or Caroline Mulroney.

Mr. Ford does not appear to have rejected that offer, yet. But his first week on the job seems to have been a struggle to figure out just how much he wants to conform to the usual expectations of a party leader and whom he trusts to help strike the right balance between that conformity and being true to his family’s populist political brand.

That tension has been evident, partly, in how Mr. Ford presents himself in public, flirting with normalcy but still rankling Tories who expect a certain level of discipline.

Mr. Ford has been visibly trying to reassure Ontarians who fear he is as much of a bull in a china shop as his late brother Rob proved while Toronto’s mayor, or as Donald Trump. With infrequent exceptions, he has been respectful toward political adversaries, polite to media, unthreatening in tone. He has made the right noises about Tories coming together to defeat Ms. Wynne’s Liberals and sometimes, fallen back on talking points when interviewers have asked about thorny topics such as his social conservatism.

But he also embarked on media interviews obviously lacking much knowledge of what the government he seeks to lead actually does, leading to an angry confrontation with a CBC host that got enough attention to undo some of his hard work to play against perceived type. And when more in his comfort zone he sometimes veered onto ground no other PC leader would – his claims he would lead his party to a historically large victory, for instance, boastful in a way that did not exactly discourage Trump comparisons.

Even Mr. Ford’s comments in support of private rather than government-run marijuana sales raised some eyebrows among Tories. Since when were they more liberal than the Liberals on pot? Was it part of any broader strategy, or just freelancing?

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That last question was especially tricky, because amid some degree of behind-the-scenes jockeying, it was still being determined who had the leader’s ear and the organizational reins.

At the start of the week, word out of Mr. Ford’s camp was that his leadership campaign manager Michael Diamond – a protégé of Nick Kouvalis, once the best-known backroom figure in the Fords’ world – would run his general election campaign. Then it was that Kory Teneycke, former communications director for Stephen Harper and short-lived Sun News executive, had taken control. Then the campaign-manager talk centred on Chris Froggatt, an Ottawa lobbyist who was John Baird’s chief of staff during his early cabinet days.

Meanwhile, Dean French – a confidante of Mr. Ford last prominent in party politics as a Canadian Alliance organizer under Stockwell Day – was said to be serving as campaign chair, with much clout in personnel decisions. Other semi-familiar names surfaced, among them city councilor Michael Ford (the leader’s nephew) and former MPP Frank Klees.

If all these folks have anything in common (aside from mostly being white and male), it’s that none are currently members of the Conservative political establishment. Whether because of their own choice or personality conflicts, never having impressed the right crowd or time having seemingly passed them by, they are not part of federal leader Andrew Scheer’s team; few if any would be playing key roles for other provincial leaders.

Mr. Ford isn’t gutting his party’s entire infrastructure; many of the mid-level staff and organizers from Mr. Brown’s era are staying. And more prone to seeking approval from powerful people than he prefers to let on, Mr. Ford may yet be persuaded to surround himself with more of an Albany Club crowd, instead of the relative outsiders now at the highest levels.

It would be easy to make a case for the steadiest possible hands, capable of crafting the safest possible campaign. Opinion polls, after all, suggest the PCs could beat Ms. Wynne with just about any leader, so long as they don’t yet again find a way to beat themselves.

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But then, Mr. Ford is not any leader. Those around him may have to embrace some chaos.

His current crowd may be more suited to that than the usual suspects. Other Tories view many of them with some of the same skepticism they did Mr. Ford until a week ago. Perhaps together, they can figure out how much they want or need to prove their detractors wrong.