It was an effort to rally the troops from a campaign on the ropes.

An internal letter from John Laschinger, the man masterminding Olivia Chow's bid to become Toronto's next mayor, outlined a change of direction as the former NDP MP collapsed in the polls.

"Let's be clear," Mr. Laschinger wrote to Ms. Chow's supporters in the days before Labour Day, when the campaign would begin in earnest. "Ford and Tory are not progressive. Olivia is."

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Mere months before, Ms. Chow was the undisputed front-runner, all but certain to end the Ford era and lead a left-wing tidal wave back to power at city hall.

But now she was badly trailing John Tory according to a poll done by Forum Research in late August and faced the ignominious prospect of finishing behind Rob Ford himself.

Through conversations with campaign insiders, both on and off the record, The Globe and Mail has pieced together the behind-the-scenes story of how it went wrong – and Ms. Chow's hail-Mary plan to turn it around.

In part, the campaign's problem was picking the wrong target – going after Rob Ford instead of John Tory. As well, Ms. Chow did not stake out a progressive enough place on the spectrum, and failed to get her message across, sources close to her say. Sources close to Ms. Chow also blame the NDP's ill-received provincial campaign in June – which ditched big-picture progressivism for small-ball populism – for rubbing off on Ms. Chow's brand.

Now, with Rob Ford battling cancer and his outspoken older brother stepping in to take his place on the ballot, Ms. Chow has an opening.

"I have momentum on my side," Ms. Chow said on Friday, standing on a windswept corner in Scarborough, where her proposal to bring back light rail and cancel a planned subway has failed to translate into the votes she was counting on.

The campaign plan is to polarize the race between Ms. Chow and Mr. Tory, and fight a war on two fronts, sources confide. On one, Ms. Chow will rally the left by emphasizing her progressive bona fides, rolling out new policy and arguing that Doug Ford has no hope of winning, so people don't have to vote strategically. On the other, she will look to pull in erstwhile Ford supporters who would have backed the mayor but do not like his brother. And through it all, she will launch an all-out assault on Mr. Tory's SmartTrack transit plan.

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It's now or never for Ms. Chow if she wants to be more than an afterthought on voting day.

The wrong target

The Chow campaign made the strategic mistake in the early days of focusing too much attention on doing battle with Rob Ford and too little on fighting Mr. Tory. In the early days of the race, sources in Ms. Chow's circle repeatedly emphasized how she would fight to peel away Mr. Ford's blue collar, new Canadian partisans in Scarborough and Etobicoke, in part by offering practical promises of service improvements, tapping into the sort of transactional politics Mr. Ford played in 2010.

Last spring, Ms. Chow put this strategy into action. A memoir, released before she joined the race, chronicled her experience coming of age as a new immigrant to Canada, her political victories and the heartbreaking loss of her husband Jack Layton. Others in the centre left, such as Adam Vaughan, who had aspirations about running for mayor were told to step aside. Ms. Chow was the one who would beat the mayor.

Ms. Chow made frequent stops in Scarborough in the spring, offering such things as better bus service, and online city services for small businesses. She framed the Scarborough LRT in practical terms: one source said her plan was to drum up support by targeting neighbourhoods that would be served by an LRT stop but not by a subway station. And she talked about "knowing the value of a dollar" – an assertion meant to defuse concern over her leftist credentials.

Ms. Chow's team also appears to have underestimated Mr. Tory. Early on, a campaign source took a dismissive view of the former talk show host's chances: his base of privileged North Toronto denizens was small compared with Ms. Chow's broad inner-city support. Besides which, Mr. Tory would lose many possible right-wing voters to Mr. Ford.

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Another campaign source confided at the time that Ms. Chow's team was just as worried about the underfunded David Soknacki – who made a play for urbanist voters and also supported the Scarborough LRT – as they were about Mr. Tory's well-heeled campaign.

Implicit in this calculation was the assumption Ms. Chow would win downtown and her most pressing concern had to be building support in the suburbs. But Mr. Tory has actually bested her in recent polls of the old city.

SmartTrack

Now that the Chow campaign is focused on Mr. Tory, his SmartTrack transit plan is its top target. Mr. Tory is proposing to add 53 kilometres of TTC commuter lines in existing GO corridors, and finance the city's portion of the $8-billion project through assessment growth, known as tax-increment finance.

The Chow campaign's largest mistake, one insider confides, was not pulling apart Mr. Tory's transit proposal on its obvious technical problems as soon as it was released last spring. At the time, the insider said, the then-first-place campaign's aim was to keep Mr. Tory in third and they feared that attacking SmartTrack on its merits would give it undue legitimacy.

Ms. Chow is now trying to rectify that error. She takes a shot at the plan every chance she gets – at debates, in interviews and at photo ops across the city designed to point out problems, such as the homes being built on the former right-of-way along Eglinton Avenue West, where Mr. Tory first suggested the line could run. Since then, he has said some tunnelling will be needed. Mr. Tory's campaign declined to comment on this story.

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"I think that the impact of Tory's transit financing plan being as wobbly constructed as Ford's is her real opening," said George Smitherman, the former deputy premier and one of Ms. Chow's highest-profile supports. "Tory has moved to where his radio crowd is, and I think voters will come to reject someone who builds their key platform on such a shoddy funding mechanism."

The Ford Factor

The exit of the mayor from the race has given Ms. Chow an unexpected opportunity to try and turn things around. With Doug Ford yet to join debates and the mayor no longer there to take the spotlight, Ms. Chow's organizers are hoping one-on-one debates between their candidate and Mr. Tory will work in their favour.

"John Tory is afraid of Olivia Chow head-to-head," says Jamey Heath, her head of communications who took over the campaign's war room after Ms. Chow parted ways with Liberal strategist Warren Kinsella.

Ms. Chow, who some insiders have suggested struggles in debates because English is not her first language, has gone on the offensive since she was overshadowed by the mayor and Mr. Tory in a debate at the Toronto Regional Board of Trade in early September. She has tried to make a positive out of a disadvantage, frequently saying she is not a "smooth talker or a fast talker," but instead takes action.

The move has not closed the gap with Mr. Tory, but Mr. Heath says it will take time for the "new reality," of a race without the mayor to set in.

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In the end, the Chow campaign is banking on a volunteer network of about 6,000 branched out across the city to pull in votes for their candidate on Oct. 27, rather than an air war waged in expensive advertising.

And she can take some comfort from the many veteran politicos working for her. Mr. Laschinger was the architect of David Miller's come-from-behind victory in 2003. Helping him is federal strategic guru Brian Topp, the social media savvy Jennifer Hollett and Nathan Rotman, a field work expert from the federal NDP.

But for her to have any hope of the ground game working, she must first make up some ground.

Pulling the vote can only put a candidate over the top if the gap is relatively small – say five or six percentage points – "to make it look like real a choice" on election day, said Patrick Gossage, a veteran of many campaigns who is rooting for Ms. Chow.

"Then," he said. "We are laughing."