Today's Ontario Liberal leadership vote: the contenders, the issues, the wildcards

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Will Sandra Pupatello's "electable" personality best Kathleen Wynne's cool grasp of policy? Will Gerard Kennedy, a one-time golden boy, get burned again by a risky re-entry into politics? Saturday's vote for leadership of the Ontario Liberal Party holds the key to the future of this beleaguered party.

THE CONTENDERS

Sandra Pupatello

Sandra Pupatello's signature stilettos and big hair match her personality, which tends to fill any room. She's the down-to-earth Windsor native who is quick with an anecdote to show that she understands what it's like to be frugal with the household budget or stuck in traffic gridlock.

She buys her rapini on special for 99 cents a bunch. And she finds it no fun at all to have to push her way onto a crowded subway car commuting in Toronto, yanking her handbag behind her.

If Liberal delegates choose a new leader this weekend based on "electability," party insiders say Ms. Pupatello should win. With the notable exception of economic issues – an area she knows inside out from her days as the McGuinty government's globe-trotting economic development minister – she is a bit light on the policy front. But her natural warmth and ability to charm and cajole any audience, not to mention her well-earned reputation as the Liberals' resident attack dog, make her a good bet to take on both opposition parties.

She is pledging not to fight but to reach out to the opposition if she wins and engage them in a conversation on her No. 1 issue: jobs and the economy. For the candidate who answers the phone in her campaign office when everyone else is too busy and who gains the upper hand over hardened journalists by turning on the charm ("I made your career," she told one), she just might persuade the opposition not to push the province into a snap election, something she says would be "folly."

Ms. Pupatello, 50, is married to Jim Bennett, a lawyer and member of the House of Assembly in Newfoundland and Labrador. Her father, Mario, immigrated to Canada at 19 from Friuli in northern Italy. Her mother, Ada, immigrated at 11. Ms. Pupatello first got involved in politics at 14, volunteering for local Windsor MP Herb Gray. -Karen Howlett

Kathleen Wynne

She has a thorough knowledge of policy, and is able to discuss details of everything from health care to education to public transit. Her demeanour is relaxed and low-key – traits that no doubt proved useful in her prepolitics career as a mediator.

Whether these attributes are Kathleen Wynne's greatest advantages or her worst drawbacks, however, depends entirely on your point of view.

To her supporters, they signal a woman with the competence to run a government and the patience to make deals with everyone from public school teachers to opposition leaders.

Her rivals, meanwhile, say Ms. Wynne's likeable, intellectual persona lacks the aggressiveness needed to do battle with the Progressive Conservatives and the NDP, who could topple the Liberals' minority government and force an election as early as this spring.

A Torontonian, Ms. Wynne has also had to fend off insinuations from her chief rival, Sandra Pupatello, that voters elsewhere in the province would be uneasy with a leader from the nation's largest city. Unlike Ms. Pupatello, however, Ms. Wynne has a seat in the legislature and has pitched herself as the person best able to bring the House back quickly and push the party's agenda forward.

Ms. Wynne, 59, began political life as an activist, teaming up with leftist former Toronto mayor John Sewell to form a group opposed to the creation of a megacity in the 1990s. Subsequently, she was elected to the school board, and in 2003, the legislature.

In cabinet, she worked on high-profile projects including Premier Dalton McGuinty's signature all-day kindergarten program and the controversial deal with Toronto Mayor Rob Ford over the Eglinton LRT.

If elected, she would be the first openly gay provincial premier in the nation's history, and the first woman to hold Ontario's highest elected office. -Adrian Morrow

Gerard Kennedy

It has not been an easy road for Gerard Kennedy to his second bid for the Ontario Liberal leadership, more than 16 years after his first. Once a fresh face, the former food-bank director is now a battle-worn political veteran scarred by a disappointing federal foray that ended when he lost his seat in 2011.

His entry into this race was risky, because a poor finish might cost the one-time golden boy the lustre he has left. Many supporters cautioned him to stay out, but he pressed forward – motivated, at least in part, by the belief that he was the only one who could shake up a party that had lost its way in his absence.

That slightly messianic view of himself has long made Mr. Kennedy a polarizing figure among Liberals. Some have an almost cultish attachment to him, lauding his social conscience, his work ethic, his record as the province's education minister and his anti-establishment streak. Others contend that he has always been better at talking than getting things done, and resent his return.

Whatever else, Mr. Kennedy remains a consummate outsider. He has spent much of the campaign criticizing his party as too centralized, and promising to overhaul its structures. He has also been the only candidate to express strong disagreement with the Liberals' recent fight with teachers' unions, promising the sharpest break from the current path.

Personally charismatic, he has a higher profile with the general public than any other candidate. But members of his party are not warming to him, and he comes into the convention with just 14 per cent of delegates. - Adam Radwanski

THE ISSUES

The Economy and Jobs

"I feel like I'm doing exactly what I should be doing: focusing on jobs and the economy," said Ms. Pupatello, who left provincial politics in 2011 after 16 years as an MPP. "If the [McGuinty] government wanted that to be the conversation, that's not what people were hearing on the outside. It really is the No. 1 issue. We really need to get back to that."

Health Care

"We want to be a lot more creative. We take the incentive out of the health-care system. If [health-care providers] save money, they should get rewarded, not penalized. Eric Hoskins lived and breathed that at the local level. We can … encourage local innovation and do it for less money."

Transit

"I'd like to start a conversation with the federal government that isn't in an antagonistic way, but just to point out really clearly and make a really good solid economic argument [for Ottawa to] fund transit on an annualized basis. They do that everywhere except [Toronto]. It's in their best interests to participate."

Green Energy

"I think everybody would agree, even the government would agree, the green-energy program has not been perfect. I will say it was exactly what Ontario needed when it was launched. Ontario needed to be put on the map. That was very successful. To this day, our financial community receives calls from investors all over the world."

Governing in a Minority

"I actually want to work with this government. My first two calls will be to [Progressive Conservative Leader Tim] Hudak and [New Democratic Party Leader Andrea] Horwath. I know jobs and the economy is their big focus. If we actually say that's our priority, I don't know how they could not work with us. Even Horwath talks about jobs and the economy." - Karen Howlett

SHOCKING UPSETS NOT SO UNCOMMON AT DELEGATED CONVENTIONS

As Gerard Kennedy could attest, delegated conventions can produce stunning upsets. In 1996, he came into the provincial Liberal leadership with a big lead, only to be defeated by Dalton McGuinty, who entered the convention in fourth place. A decade later, he played kingmaker as Stéphane Dion pulled off a similar shocker at the federal level.

Such surprises are highly unlikely this time because of the large gap between the two front-runners and the rest of the field, and because neither Mr. Kennedy nor fourth-place candidate Harinder Takhar really fit the profile of compromise candidates.

Still, sources in both Kathleen Wynne's and Sandra Pupatello's camps claim to have heard the term "gentlemen's club" being thrown around to describe organizational efforts to vault one of the four male candidates – a group that also includes Charles Sousa and Eric Hoskins – onto the final ballot.

Even if their language is smarter than that, there's no question that conversations between the long-shot candidates are taking place. That could at least produce some twists and turns along the way. - Adam Radwanski