When Olivia Chow first entered the 2014 campaign to become Toronto’s next mayor she was considered the overwhelming favourite to win the race against Rob Ford and John Tory.

Her name recognition was high as an NDP MP and as the widow of the late Jack Layton, she had raised lots of money, had an experienced campaign team, a “bulletproof” election platform and hundreds of eager volunteers.

But after leading the polls for months, her campaign eventually faltered badly and she finished a distant third behind the winner Tory and runner-up Doug Ford, who replaced his ailing brother Rob in the last weeks of the campaign.

So what happened? How did this high-profile, seasoned politician crash and burn so badly?

Now, in a revealing new book by John Laschinger, her former campaign manager, voters can get an insider’s look into the backroom secrets and strategies of one of the most critical elections in recent Toronto history.

As Laschinger sees it, Chow’s dream of being Toronto’s mayor ran into a wall of bad luck, bad timing, blatant racism and sexism — and a possibly fatal overall campaign strategy.

In his book, “Campaign Confessions:Tales from the War Rooms of Politics,” to be released by Dundurn Press on Sept. 10, Laschinger also offers critical insight into why Tory won in 2014 and why Rob Ford was so successful in his 2010 mayoral bid.

It’s an important book because Laschinger is considered to be Canada’s lone full-time professional campaign manager. In Toronto alone he has headed David Miller’s successful 2003 mayoral bid and managed Joe Pantalone’s third-place campaign in 2010. Over the last 45 years, he has been involved in 50 political campaigns, winning 30 of them.

In 2014, Chow was cruising to victory well into June. But then she started to run into trouble that her team failed to predict — and failed to overcome.

First, the provincial Liberals under Kathleen Wynne swept to a majority victory in the June 12 election. In Toronto, the NDP lost three of its five seats, including Chow’s old federal riding of Trinity-Spadina. It was a shocking setback for Chow because it threw into question her supposed “lock” on downtown wards.

Second, Rob Ford returned from addiction rehab on June 30, where he had been since May 1, and re-entered the race.

Chow and Laschinger were stunned by the number of voters willing to give Ford a second chance, undermining the lead she had built as the main anti-Ford candidate.

“Suddenly, Ford, rehabilitated, was not the Darth Vader of municipal politics,” Laschinger writes. “He seemed to a number of people to be a stronger candidate than he had been before rehab. That unsettled the two-thirds of Torontonians who had all wanted to be rid of Ford. Although not everyone believed that John Tory’s policies were sound, he seemed to have grabbed the anti-Ford mantle.”

Third, Chow was the target of what Laschinger describes as “some of the most appalling racists, sexist and vulgar abuse I have had the misfortune to witness in my life in politics.” It disgusted him and it should disgust all who care about this city. Much of it originated with the supporters of the Ford brothers, he says, with Chow getting a steady stream of hate mail and having one man yelling for her to “get the f--- out of here. This is Ford Nation, bitch.”

By late July, secret focus groups were telling Laschinger that while voters liked Chow’s progressive policies, they equally wanted a right-of-centre mayor to keep costs under control. “This placed Chow in a tight spot,” he writes. “As a member of the NDP she was seen as progressive, but also many saw her as a “tax-and-spend socialist.”

In anticipation of this, Chow had adopted a defensive strategy of presenting her story as a child of a poor immigrant family who need to watch every penny it spent and as a city councillor who helped prepare seven balanced budget under former conservative mayor Mel Lastman.

At first, the strategy worked. But it began to go badly when Chow’s progressive supporters in downtown areas started to abandon her to support Tory. “They felt that he was a real conservative who would control spending and at the same time he was progressive enough, at least compared to Rob Ford, to satisfy their desire for a progressive mayor,” Laschinger concludes.

By mid-September, Chow’s poll numbers were dropping rapidly. She never recovered.

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Did Chow’s team screw up by urging her to tout her fiscal credentials instead of continuing to put her progressive ideas at the forefront of her campaign? Or as Laschinger says, was she simply “doomed from the start by the political cards she was dealt?”

Even Laschinger isn’t sure. What is certain, though, is that, as he suggests, political scientists will debate Chow’s election strategy for years to come.

Bob Hepburn's column appears Thursday. bhepburn@thestar.ca

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