09/14/2013 01:47 EDT | Updated 11/14/2013 05:12 EST

Toronto byelection candidates to be picked Sunday

Both the Liberals and NDP have scheduled nomination meetings tomorrow to choose their byelection candidates in one of the most closely watched ridings in the country.

The downtown riding of Toronto Centre, recently vacated by the former interim Liberal leader Bob Rae, is a mix of public housing alongside some of the most expensive real estate in Canada. It contains a politically active gay village, a large university and a widely diverse electorate.

It’s a “pedigree” riding that has traditionally carried some clout, where the voters expect to be represented by cabinet ministers, or at least, heavy-duty critics, as in the case of Rae.

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Toronto Centre has been Liberal for years, held by star MPs such as Rae and Bill Graham, who was also an interim party leader. As well, it's where about 80 per cent of the top Liberal strategists in the party live and work.

The byelection race is attracting much attention, partly because the stakes are so high for both the Liberals and NDP.

According to Alice Funke, who runs the blog Pundits' Guide to Canadian Federal Elections, for the NDP it’s a case of "would have, should have," given that it increased its vote in Toronto Centre by 15 per cent in 2011, and "put quite a good scare into the Liberals during the provincial election."

A win would give the NDP the downtown Toronto core and might pave the way for a trifecta when Toronto Centre morphs into three new ridings after election boundary redistribution for the 2015 election.

For the Liberals, a loss would be "just terrible for Justin," says a Liberal strategist, meaning that under the new leader’s watch the party couldn't hold on to a decade-old Liberal seat.

It was the NDP that first nailed down the Sept. 15 date to nominate a candidate. When the Liberals subsequently seized on that same day, some said it was because they didn't want the NDP to monopolize a "media day."

Whatever the reason, the contests will determine the two front-runners — an NDP and a Liberal candidate — in a yet-to-be-scheduled byelection, though many believe it will occur in late fall.

Chrystia Freeland, a high-profile journalist and author who's worked in London and New York, left her job as managing editor at Thomson Reuters to move back to Toronto and run for the nomination. She is said to be a star candidate recruited by Liberal Leader Justin Trudeau, but Trudeau has promised open nominations in all ridings, so she must compete for the job.

Also running for the Liberal nomination are Diana Burke, a former banker, and Todd Ross, a longtime Liberal activist and organizer in the riding.

Freeland will be introduced by former Ontario cabinet minister George Smitherman, who told CBC News in June he wanted to run himself. By July he said he was stepping back, writing in the Huffington Post he endorses the "leader's strategy."

Liberal insiders expect Freeland to win, though many are dismayed the party retroactively established a membership cut-off date. One strategist who didn't want to be named thinks the cut-off of Aug. 20 was deliberately chosen for a time when half the riding was out of the country or at their cottages, and wasn't announced until 13 days after that date. "The trigger was pulled by the centre," he said, meaning Trudeau's office.

Funke in her blog has followed the Toronto Centre contest closely, meeting candidates and attending meetings. She said in an interview she believes up to 600 potential voters were eliminated, mostly ethnic minorities, who support either Burke or Ross.

Funke thinks Freeland will probably win the nomination. "Within the [Liberal] culture, there is a tendency to do what the leader wants."

If she doesn't, some Liberals say, it means Trudeau would be handicapped in his quest to persuade other star candidates to take a shot at nominations for the 2015 election.

The NDP nomination is also being sought by some high-profile journalists.

Jennifer Hollett, a former MuchMusic VJ who has also worked for CBC, started organizing early, and Funke thinks she may have signed up a lot of new members.

Linda McQuaig, a well-known Toronto Star columnist and a prolific book author, is seen by some as the establishment NDP candidate, "someone NDPers would have been waiting for, for so long," Funke said.

Funke says she can't tell who's ahead between the two rivals, and an NDP strategist agrees.

The third NDP candidate is transgender activist Susan Gapka, who didn't enter the race until after membership sign-ups were closed, meaning she can rely only on active members for votes.

The Conservatives have one candidate so far, lawyer Geoff Pollock.

John Deverell, a former Toronto Star journalist, is running for the Green Party nomination. Travis McCrea, the Pirate Party's national leader, is also a candidate.

Three other byelections are coming up as well. One will be in the Montreal riding of Bourassa vacated by formal Liberal MP Denis Coderre, who is running for mayor of Montreal.

Two more byelections are in Manitoba, in the riding of Provencher that belonged to former Conservative cabinet minister Vic Toews, and in Brandon-Souris, left empty by the resignation of Conservative MP Merv Tweed. No dates have been set for these byelections.