I came across an old campaign button the other day. It features a black and white depiction of Queen's Park and the words: "More Women on Top."

And by tomorrow afternoon or, early evening (here’s hoping the Liberals don't take two days to elect a leader as they did in '96 with Dalton McGuinty) a woman will very likely be on top as the new Liberal leader and, automatically premier of Ontario.

It'll be a first for this province though it'll come almost two decades after tiny Prince Edward Island had a woman premier in Catherine Callbeck and on the heels of women premiers in Newfoundland and Labrador, Quebec, Alberta and British Columbia.

In the 1990s, Ontario Liberals did elect a woman leader, even though some in the party were not convinced Lyn McLeod, while likeable and solid in her cabinet portfolios, would be able to make the leap to leader and premier against the Conservatives' "Common Sense Revolution" and Mike Harris.

They turned out to be right. The Liberal campaign fell apart, in part because some in the party sat on their hands, unable or unwilling to accept that McLeod, a woman, was leader.

But for Kathleen Wynne and Sandra Pupatello, it’ll become a question of for how long?

The current polls would suggest neither redecorate the premier's office since the paint may not have dried before there is another election or, that PC leader Tim Hudak or Andrea Horwath may not like the colour scheme.

And, that's because no matter what you hear from the Liberals this weekend about winning the next election, it's a long way from a certainty and the rebuff the party took in last fall’s Kitchener-Waterloo byelection more of a potential reality, province-wide.

So, as delegates vote tomorrow in the Ryerson University basketball court — a part of the Mattamy Athletic Centre a.k.a the former Maple Leaf Gardens — with Pupatello likely to have a slight lead on Wynne, it may well be in the minds of many that they are electing a leader who will lead them to the benches on the left and not the right of the Speaker at Queen's Park. From government to opposition.

Ontario will make history if either Sandra Pupatello (left) or Kathleen Wynne (right) win the Liberal leadership and succeed Dalton McGuinty as premier. (Frank Gunn/Canadian Press)

Both women are very bright, always well briefed and not always with a script and they can be tough. But for many Liberal delegates Pupatello is the one they remember from her days in opposition, verbally trashing Conservative cabinet ministers and relishing the role as "Dalton’s attack dog."

However, not all Liberals are entirely comfortable with Pupatello's "ready, fire, aim" approach to politics. And some are concerned by her decision to get a seat in the Ontario legislature (likely Windsor-Tecumseh from old friend Dwight Duncan) and then recall MPPs to resume a sitting interrupted by McGuinty's decision to leave.

And, for some Liberals there’s an additional concern that Pupatello as premier might be inclined toward calling a quick election, trying to capitalize on opposition parties lacking funds and in some cases, candidates.

The risk, of course, is that voters might not take kindly to spending millions of their dollars on an election just 17 months or so after the last one, especially when the Liberals are already under the gun for the lost hundreds of millions at e-Health, Ornge Air Ambulance and the closing of not one, but two power plants — one of which was half-built.

For Wynne, there is the obvious and frankly oft-repeated mantra that she has a seat in the legislature and wants the business of the legislature back by February 19th.

Wynne's CV includes a certificate in mediation from Harvard University. And its inclusion is not by accident. It is meant to say if, as premier, she has to negotiate with the opposition and teachers, she’s got the training to get it done. But also unsaid is that she might have a willingness to keep the parliament going to avoid an election for, say, a year or so. Maybe longer.

But apart from all the positives there is still one lingering question. If she wins the convention, can she win the province?

Opinion on that is divided especially when her sexual orientation is factored in, even though she has never hidden the fact that she's lesbian.

For some Liberals — even in Toronto — it is as they say "the elephant in the room" but also something they don't or wouldn't want to talk about publicly. But it is and has been through the leadership a discussion in some backrooms.

Still, with the positives and negatives of both front-runners. This is a real race between Wynne and Pupatello and it will be the four male candidates who become the "queen-maker" tomorrow — another first in Ontario politics and another giant step along the road to saying good bye to the province’s oldest running 'Boys Clubs!'