An inside look at how John Tory’s too-late move may have helped Olivia Chow become mayor

As Ana Bailão’s campaign team busily worked in her Dundas Street West campaign office on a Wednesday morning with only days left to catch Olivia Chow in the mayor’s race, they were given a shocking order: get out.

Senior staff ushered the flustered workers and volunteers out the door. Quiet fell on an office that had been abuzz. As the troops huddled in a cafe downstairs, a campaign office door opened and in strode the man they had long awaited: John Tory, the fallen king who they hoped would play king maker. The former mayor was finally about to endorse Bailão’s struggling campaign.

Tory’s endorsement would end up being a pivotal moment in the final days of a mayoral contest that went from what looked like a Chow coronation to a nail-biting election night finish on June 26. Its impact on the race is still being debated a week after the vote, and speculation about whether Tory could have blocked Chow’s path to the mayor’s office will likely swirl for longer.

The former NDP MP ended up winning by 34,000 votes. But detailed election results the city published Friday reveal a stunning twist at the end of the campaign: Bailão received almost 216,000 votes on election day to Chow’s 209,000. What clinched Chow’s final victory were advance ballots cast before Tory weighed in: Chow trounced Bailão, collecting 60,000 to Bailão’s 19,000.

The Star spoke to insiders in the main candidates’ camps to piece together what happened in the race’s closing stages, and to try to answer a key question: why didn’t Tory endorse Bailão sooner?

John Tory faced increasing pressure to back Ana Bailão

Tory didn’t respond to requests for comment for this article. The former mayor has been largely out of the public eye since his shocking resignation in February over an affair with a member of his staff.

Bailão also declined to answer questions, but in a statement said, “we ran an incredible campaign” and she was “grateful” to Tory and everyone else who endorsed her.

But according to multiple sources, as the mayoral campaign entered its final month and Bailão failed to launch, Tory was facing increasing pressure from senior members of her team to break his pledge to stay neutral in the race, and publicly declare he was backing her.

Her team felt she was running a solid campaign. Donations were pouring in and the former councillor for Davenport was racking up support from council members and MPs. But in a mostly drama-free election, it wasn’t clear voters were paying attention, and nothing she did seemed to move the needle.

And Bailão herself, hugely admired at city hall for her work on affordable housing during her three terms on council, came off in some debates as an exasperated policy wonk, throwing around housing jargon and sometimes losing exchanges to Chow, who was supposed to be the poor debater.

Bailão’s campaign team was made up of many of the same veteran operatives who helped Tory to three consecutive election victories, like campaign manager Tom Allison, pollster Nick Kouvalis and adviser Patrick Harris. She was supposed to coast in on the former mayor’s coattails. Voters still loved him but they also wanted change. Somebody like Tory — but without Tory — wasn’t enough.

“I know Ana’s campaign was heavily, heavily pressuring John to endorse. She could become a lot more competitive, they had all the pieces in place but needed a boost and he could give it,” said one source with knowledge of the discussions, who like others in this article requested anonymity to discuss internal deliberations.

Yet at the same time some of Tory’s long-time advisers, even some who were helping Bailão, were telling him it was in his best interest to stay out of the race. Tory has never publicly answered questions about his relationship with the staffer, and when he resigned he said he planned to work to regain his family’s trust. Some close to him believed that if he re-entered public life by commenting on the mayor’s race, he risked rehashing the scandal and putting his estranged wife and grown children through another ordeal.

Some doubted whether a Tory endorsement would help Bailão enough

Tory advisers opposed to the endorsement also doubted whether Bailão could beat Chow, even with his support. While Bailão’s internal polling showed she was performing better than most publicly released polls, it wasn’t clear she was in striking distance of Chow. If Tory publicly tied himself to a candidate who didn’t win, his public reputation could go from that of a popular ex-mayor to a loser who had broken his promise and couldn’t help an ally get elected.

“The polls were s–t” for Bailão, said one person close to both her campaign and to Tory. “Why does the guy go out, put his head in the blender, if she’s at 10 or 12 points?”

Two sources told the Star that in early June, with advance voting set to begin, Tory informed Bailão he wasn’t ready to give her his nod. He told those close to him he wasn’t endorsing, “because he didn’t want to put his family back in the spotlight,” according to the first source.

Almost 130,000 people cast a ballot in six days of early voting between June 8 and 13, which ended up being almost one-fifth of the total turnout. It was a turning point — with those votes baked into the final result, anything the candidates did in the final two weeks would have a diminished impact on the June 26 election.

None of the sources who spoke to the Star had direct knowledge of why Tory reversed course and decided to endorse Bailão in the final days. But some speculated that two developments gave her enough momentum to convince Tory an endorsement would be less risky.

First, on June 16 Deputy Mayor Jennifer McKelvie, who had also promised to stay out of the mayor’s race, flip-flopped and announced she was backing Bailão. Then on the morning of June 21, the Star editorial board issued its own Bailão endorsement.

Tory secretly records messages of support

Hours later, Tory was at Bailão headquarters to record messages of support. In an effort to shield him from the media, his arrival was kept from all but a handful of senior campaign staff.

The whole affair was so hasty and secretive that Allison, Bailão’s campaign manager, later held a call to apologize to staff upset they hadn’t been kept in the loop.

Shortly after Tory left Bailão’s office, her campaign released a statement and video in which he described her as “the best choice to lead this city forward and to bring it together everyday as I tried so hard to do.”

A robocall he recorded supporting her was pushed out to one million phones, and her campaign delivered flyers trumpeting Tory’s statement to homes across the city.

Brad Bradford incensed at Tory’s endorsement

News of Tory’s endorsement incensed another candidate, Coun. Brad Bradford. Tory had encouraged both Bailão and Bradford to run, and according to the Bradford campaign, the former mayor acted as the councillor’s sounding board, right up until hours before the endorsement when the pair chatted after a First Nations sunrise ceremony outside city hall.

“Tory gave Brad no hint he was about to endorse Bailão,” said Matt Hiraishi, Bradford’s campaign manager, to whom Bradford directed questions about the endorsement. “Brad had hoped John would at least give him the courtesy of a head’s up”

After news of the endorsement broke, Bradford tweeted: “Yesterday’s politicians aren’t the answer to today’s problems.”

Tory took offence, Hiraishi said, and Tory and Bradford had a “heated” phone exchange. Tory also texted Bradford that he had intended to call him before the endorsement was announced but word leaked early. A Tory text to Bradford, read out by Hiraishi to the Star, included: “Your tweet about old has-beens and such was unnecessary and inconsistent with what we discussed about you as a classy, intelligent person.”

Bailão sees a bump in the polls, Saunders loses support

The effect of Tory’s endorsement appeared to be immediate. A Forum Research poll conducted two days afterwards showed Bailao’s support jumped 7 points, to 20 per cent. Chow was at 29 per cent.

Laryssa Waler, campaign manager for former police chief Mark Saunders, said after Tory’s endorsement when his team went out door-knocking “we could feel a massive shift” as voters opposed to Chow abandoned Saunders and coalesced around Bailão.

One source close to the Saunders campaign acknowledged that Tory’s endorsement made Bailão the “stop Chow” candidate, a title the former police chief had worked hard to try to claim.

Olivia Chow campaign dismisses the effects of the Tory backing

The response from Chow’s camp was muted. On June 21 she released a brief statement downplaying Tory’s endorsement, as well as Premier Doug Ford’s public comments backing Saunders. It said Tory and Ford only amounted to “two votes.”

“They don’t get to decide the next mayor of our city, the people do,” she said.

Chow’s spokesperson Shirven Rezvany said the endorsement “had very little impact on our own campaign.”

“Olivia remained focused on connecting with the people and sharing her message of building a more affordable, safe and caring city. It’s clear her message resonated with Torontonians tired of the status quo,” he said.

A senior Chow campaign official, who requested anonymity to disclose confidential strategy, said they had heard Tory was facing intense lobbying both for and against endorsing Bailão, and they weren’t surprised when he finally backed her.

The source said Bailão’s campaign had always been focused on endorsements because unlike Chow, who is a nationally known former federal politician with decades of public service, she had low name recognition citywide, and had to rely on more prominent people to boost her profile. They believed Tory’s endorsement helped make Bailão look like the best alternative to Chow for right-leaning voters, and caused Saunders support to collapse.

Tory backing gives Chow’s campaign energy

But the official said Tory getting involved also gave Chow’s campaign a lift. The former school trustee and Metro and city councillor had been far ahead in most polls since she entered the race in mid-April, and there was a risk of complacency setting in. The Chow campaign got an influx of volunteers and donations after Tory and Ford endorsed her rivals.

“There was a lot of energy in the final days of the campaign,” they said.

For a few dramatic moments on election night, it looked as though Tory’s intervention might prove decisive. As the first returns came in just after 8 p.m., Bailão jumped out to an unexpected lead. But as more results were tallied, Chow pulled ahead, and she ultimately won with about 37 per cent of the vote. Bailão lost by less than five per cent.

Members of Bailão’s team who had been begging Tory to endorse her earlier were left fuming. They believed if the former mayor had publicly backed her in early June she would have had a chance of closing the gap with Chow.

One senior Bailão adviser said Tory “owed it to his team of people who supported him all these years” and were now working for Bailão, and his late endorsement was yet more proof of a failing that the former mayor has been accused of throughout his career: he’s a ditherer.

“John has always been someone who can’t make any decisions, and then he needs to be forced into making any decisions. And then when he finally makes a decision, it’s like it’s a compromise of compromises where he makes no one happy,” the source said.

Sources question timing of Tory’s backing

The source said Bailão’s team was grateful Tory backed her, but many were “disappointed that he just didn’t do it when it was going to be the most effective.”

Another source close to the campaign agreed that Bailão needed Tory’s help in early June so she could firmly position herself, rather than Saunders, as best-placed to beat Chow. “That was the moment,” the source said.

However, some Bailão campaign members aren’t convinced an earlier endorsement would have made a difference. Deb Hutton, a senior adviser, said voters weren’t tuned into the race until the final days, and Saunders’s campaign made a “strategic mistake” by trying “to become the ‘anybody-but-Chow’ candidate too early. He finished third with less than nine per cent.

Hutton and others felt Chow had strong name recognition and her message appealed to a lot of voters. Bailão needed to build momentum before she could credibly claim to be the best candidate to catch her.

Tory’s endorsement “was the most significant event of the campaign” and Bailão’s team did its best to maximize its impact, Hutton said, but she didn’t fault Tory for not stepping in sooner.

“There is a school of thought that (as a former mayor) you let everyone else decide who your successor is,” and don’t try to tip the scales, she said. “It’s never an easy decision.”

Allison, Bailão’s campaign manager, said he “didn’t have time to feel frustrated” that the endorsement didn’t come earlier. “I just wanted to get the news out to as many voters as possible so that it could be part of their consideration of Ana.”

Ben Spurr is a Toronto-based reporter covering city hall and municipal politics for the Star. Reach him by email at bspurr@thestar.ca or follow him on Twitter: @BenSpurr

David Rider is the Star’s City Hall bureau chief and a reporter covering city hall and municipal politics. Follow him on Twitter: @dmrider

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