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Presented with the scenario during an editorial board meeting this week, Sandra Pupatello laughed.

"Are you trying to talk me out of this?" she joked.

It's a little too late for that, and in any event, Ms. Pupatello does not give the impression of someone who frightens easily. But the question that was put to her, about the messy set of circumstances that would ensue if she emerges victorious from this weekend's Ontario Liberal leadership convention, is giving pause to the fellow candidates whose support she will need to put her over the top.

For Dalton McGuinty's successor as premier, the immediate to-do list – which will include choosing a new cabinet, hiring new staff, preparing a Speech from the Throne, launching an overdue budget process, trying to restore some degree of labour peace and finding common ground with the provincial opposition – will be enormously daunting. Ms. Pupatello, unlike fellow front-runner Kathleen Wynne, would have to do all that while also seeking a seat in the Legislature during a by-election.

At the least, she would be distracted, putting off not just the Legislature's return but also some of her preparation for it. Considering that the Windsor seat that Finance Minister Dwight Duncan has promised to vacate is held by the NDP federally, and that unions might flood the riding in an attempt to embarrass the Liberals, there is also a very real chance that Ms. Pupatello would lose, plunging the government into crisis.

Another possibility is also making the rounds. A good number of Liberals are speculating that Ms. Pupatello might bypass such prospects altogether, in favour of quickly plunging the province into a general election – something that she has generally seemed more disposed toward than the other candidates.

While much of this chatter is coming from Ms. Wynne's camp, it's not limited to there. Nor is it difficult to imagine how such a decision might be justified. Ms. Pupatello has pushed back against election concerns by saying one of the first things she plans to do is talk to Progressive Conservative Leader Tim Hudak and the NDP's Andrea Horwath about making the minority legislature work; she could emerge from those discussions saying that their unreasonable demands require her to seek a stronger mandate.

If nothing else, all this is driving home the likelihood that the government would enjoy more short-term stability under Ms. Wynne. That's problematic for Ms. Pupatello, because with their party trailing in the polls and in need of major rebuilding, many Liberals want to keep governing for as long as possible.

The uncertainty is particularly complicating the looming decisions for Harinder Takhar and Charles Sousa. Running fourth and fifth, respectively, the relatively right-leaning candidates are seen as more ideologically aligned with Ms. Pupatello than third-place Gerard Kennedy or sixth-place Eric Hoskins, and thus likeliest to throw their support behind her on later ballots. But Mr. Takhar and Mr. Sousa both come from suburban ridings that are far from secure – and sources say that Mr. Sousa, in particular, has expressed concern about going to the polls too soon.

Such concerns will, of course, be balanced off against other considerations, so Ms. Pupatello could well emerge as premier in spite of them. But for all that she's able to laugh off post-convention circumstances, others are finding that a bit more difficult.

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