There are so many good reasons for Conservatives to laugh off the prospect of Kevin O'Leary as their leader.

He does not appear to be terribly conservative, other than on some fiscal matters. His knowledge of how this country's government works appears rudimentary at best. He has been the only candidate to duck debates in which he might have to attempt both official languages. His commitment to their party is so minimal, he has not bothered to move back to Canada full-time while running for its leadership, and not committed to seek a seat in Parliament if he wins.

Yet, despite the entrepreneur and TV celebrity launching his campaign much later than any of the other 13 candidates in the race, the consensus in rival camps and among neutral party insiders is that he is among the top three in that crowded field, and possibly leading in first-choice support.

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Whether even that momentum could be enough for him to win the May vote is harder to gauge: It depends how his support is distributed, given a voting system in which all ridings are equally weighted no matter how many Conservatives vote there, and whether he is capable of getting second- or third-choice backing on the preferential ballot.

But his mere competitiveness is confounding enough to merit trying better to understand it. If anything, he seems the sort of candidate – from outside the party's mainstream culture, contemptuous of other politicians and liable to quarrel with caucus – to which a party might turn if it's fallen on such hard times that it's ready to blow things up. But the Conservatives have lost one election, not in terribly devastating fashion, after holding power nearly a decade.

In conversations with organizers who have been working the ground this campaign, for other candidates and for him, a few reasons for why Conservatives are nevertheless drawn to Mr. O'Leary repeatedly pop up.

They think he'll beat (or at least beat up) Justin Trudeau

The most common explanation for Mr. O'Leary's appeal revolves around antipathy toward the current Prime Minister so great among some Conservatives that it outweighs any policy-related priorities for their own party.

While all leadership candidates claim they're well-suited to taking on Mr. Trudeau in 2019, Mr. O'Leary has made that especially central to his pitch. Loud and brash, he's fashioned himself a tough guy spoiling for a fight with a rival he portrays – and many Conservatives see – as soft and ineffectual.

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Many no doubt believe that contrast would work to their party's advantage, but it may not just be about returning to power. To some Conservatives, there has been too much politeness toward Mr. Trudeau from their side of the aisle – and Mr. O'Leary's caricaturing of the PM as an air-headed "surfer dude" who serves as a front for his nefarious best friend Gerald Butts suggests he'd at least kick Mr. Trudeau in the teeth the way they'd like to do themselves.

Celebrity (and a particular perception of success) sells

Canadians used to buy tickets to see Mr. O'Leary, famous for judging business pitches on the reality shows Dragons' Den and Shark Tank, work the speaking circuit. Now, his campaign has come up with a clever spin on that. Unlike with other candidates, his events are only open to party members – an enticement for potential supporters who don't already hold memberships to shell out the $15 fee.

That's not the only way Mr. O'Leary has been able to leverage his celebrity as all candidates scramble to recruit ahead of the March 28 membership deadline. Even more helpful is a social-media following, including more than 600,000 Twitter users, that allowed him to enter the race with an usually large list of targets.

As for why his brand of fame would translate into partisan support, including from some long-time party members, a rival campaign organizer pointed to Mr. O'Leary portraying himself as the sort of success story – a self-made, risk-taking millionaire – that plays especially well with fiscal conservatives.

And again, comparisons with Mr. Trudeau enter play, with some Conservatives believing the best way to counter a celebrity Prime Minister is with a celebrity of their own – and with his campaign casting him as someone able to break through with millennials the way other Tories can't.

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He's able to cut through the drone

In a leadership campaign with an unprecedented number of candidates, standing out from the pack is a bigger challenge than usual. And plainly, Mr. O'Leary is better suited to that task than anyone else in the race.

Even without opening his mouth, he's so different in image and experience as to be easily distinguishable. And when he does talk, Mr. O'Leary's television skills – his confident, concise, catchphrase-heavy manner of presenting himself – pierces the noise.

He's playing to grassroots alienation

Even after they lost power in 2015, party higher-ups felt confident that – with roughly 100 seats in the House of Commons, and their once-uneasy alliance of old Reformers and Progressive Conservatives intact – Stephen Harper had left them on solid footing.

In retrospect, they may have been overconfident. The last campaign, in which excessive discipline over local activists was coupled with an array of mistakes made by the Tories' central campaign, brought to the fore simmering resentments that couldn't be entirely extinguished with mea culpas from the party apparatus.

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Rebelling against the Conservative establishment probably isn't the primary motivation for most of Mr. O'Leary's supporters. But he might not be getting the same traction, some of the people working the ground this campaign suggests, if heading into this race the party faithful had felt more respected and more attached to the way things were done previously.