How John Tory decided to resign: the inside story of an agonizing week

Members of mayor’s inner circle describe their shock and dismay to the Star over a scandal that almost no one saw coming as the crisis at City Hall deepens.

Thestar.com
Feb. 13, 2024
David Rider

John Tory’s hopes of remaining mayor of Toronto -- a job he treasured, one that finally made him a political winner -- withered over the past week to a grim but undeniable conclusion: he had to quit.

Several advisers involved in the agonizing conference calls, and others in Tory’s circle of friends, spoke to the Star after the paper shocked the city by revealing his inappropriate, extended relationship with a former staffer.

Many who know the patrician 68-year-old were just as blindsided by revelations of wildly rash behaviour from a buttoned-down politician who had made boring a winning brand at city hall after years of earlier electoral failures.

“Part of me is hurt,” said one adviser who, like the others, requested anonymity to be able to reveal confidential discussions. “I never would have expected this kind of reckless and selfish behaviour. Many people are feeling the same way.”

It was an open secret in political circles that Tory’s marriage to Barbara Hackett was strained. People noticed she was not visible at Tory’s Oct. 24 re-election party, unlike past victory fêtes. Nor were their four adult children.

Tory and Hackett once made public appearances as a doting power couple. As the pandemic wore on, he kept his gruelling work schedule in Toronto while Hackett was, he told friends, often at their waterside home in Florida.

Last Wednesday, during a regular appearance on “Breakfast Television,” Tory was asked about Valentine’s Day plans and “who is more romantic in your relationship, you or your wife?”

Stumbling over words, an impassive Tory replied: “Oh it’s hard to know that. It’s one of those things where I try to be and make sure my feelings are known. Everyone is different. But I think men of a certain generation perhaps, including mine, are not as good at that as they might be, let’s put it that way.”

In December, when the Star was tipped that the marriage was in trouble, a Tory aide said the mayor didn’t think his marital status was a news story and he was concerned about the impact such coverage could have on his children.

In early February, the Star learned that Tory had been seeing a much younger woman who had worked in the mayor’s office. Word leaked to some other news organizations. Reporters’ feelers on the subject were reported back to team Tory.

Tory’s chief of staff, Courtney Glen, and Don Peat, a former reporter and one of her deputies, formed a “war room” to deal with the unfolding crisis. Amanda Galbraith, a former Tory spokesperson on parental leave from crisis communications firm Navigator, agreed to remotely offer them guidance.

While they strategized, Tory worked the phone seeking solace and advice from a kitchen cabinet of allies that over the days grew to include his former chief of staff Luke Robertson, political strategist Nick Kouvalis, communications consultant Bob Richardson and his 2022 campaign manager, Patrick Harris.

Some involved say a deeply embarrassed Tory didn’t announce all the details of his misconduct, so different advisers and staff had different levels of knowledge.

“People have been aware of the situation for a while, but not the extent,” one longtime adviser said. “It’s safe to say many staff are disappointed and pissed off.”

There was talk of proactively releasing a statement on Sunday, Feb. 5, or the next day, to limit the news cycle. But then Tory would have had to face questions at city council on the Tuesday.

Tory’s lawyer Peter Downard was brought into the conversation, as were Hackett and her advisers, said one person with knowledge of the deliberations.

A source close to the couple said family members, including Hackett, pushed him to resign. Peat, the Tory spokesperson, disputed that characterization, saying the mayor wanted to focus on his family.

Hackett has declined to comment to the Star on the “personal” matter.

The crisis deepened last Thursday when the Star, after further investigation, submitted more questions with details about the relationship. They included queries about “#MeToo” implications and if Tory had helped the woman get a job at Maple Leaf Sports and Entertainment after she left the mayor’s office.

Tory, long under fire for retaining as mayor his seat on the Rogers family trust, with a $100,000-per-year payment, now faced a potential firestorm thanks to Rogers Communications’ 37.5 per cent stake in MLSE.

An MLSE spokesperson said “the employee in question was hired on the basis of merit and we were unaware of any relationships other than those that were purely professional.”

Edward Rogers and Tony Staffieri, chairman and CEO of the telecom company, respectively, are both on the MLSE board. Asked whether they were ever contacted by phone or email by Tory about the former staffer, company spokesperson Sarah Schmidt said they were not. “We were not aware and we had no involvement.”

Board member Dale Lastman told the Star, “I’ve never spoken to John Tory in my life about the employment of this woman.” The Star has been unable to reach Larry Tanenbaum, who chairs the MLSE board and co-owns the company along with Rogers and Bell.

Bell referred a Star request for comment to MLSE.

The woman, whom the Star is not naming, has not responded to Star inquiries.

The mayor had to tell his team one key detail: did the relationship begin while the woman was working for him or, as one adviser had earlier insisted to the Star, after she had left city hall? Tory admitted he started seeing the woman while he was her boss.

His timeline -- the relationship started during the pandemic, and ended early in 2023 -- meant he was in an illicit relationship with a former employee while he campaigned for re-election last summer and fall, and when he privately asked Premier Doug Ford for unprecedented “strong-mayor” powers. He has also ignored warnings from some friends that third terms in office rarely end well.

His advisers started mulling what had seemed unthinkable only days before -- that Tory, who had repaired Toronto’s international reputation after Rob Ford’s prolonged crack drama, might not survive a scandal almost nobody saw coming.

“Every scenario people gamed out ended with him resigning,” one adviser said.

The best-case scenario was that his popularity, which had slumped since October’s election, tanked as he begged for forgiveness. The public would debate his behaviour while reporters derailed official events asking about his private life.

Worst case -- an integrity commissioner investigation subjects everyone involved to interviews, ending with a scathing report that forces him to resign.

Tory was adamant, sources say, that the young woman not suffer publicly because of his “serious error in judgment.” Social media is not kind to young women in sex scandals.

The Star continued to press Tory for answers into Friday, when his calls to allies yielded an almost unanimous opinion -- if he did not resign now, his beloved city, desperately in need of steady leadership, would stay mired in controversy until he was forced to quit later.

Tory started breaking the news to family members and friends. At 6:33 p.m., his lawyer emailed the Star a statement confirming the allegations. The Star broke the news one hour later.

At 8:30 p.m., a grim-faced Tory strode into the part of his city hall office used for news conferences, thanked reporters for coming and said: “I’ve decided that I will step down as mayor so that I can take the time to reflect on my mistakes and to do the work of rebuilding the trust with my family.”

The admission threatens to put Tory’s leadership into doubt and the government of Canada’s largest city into turmoil just months after the 2022 municipal election.
He wryly noted that, while he often welcomed reporters’ questions, this time he would let his bombshell speak for itself.

As of Sunday, Tory hadn’t officially resigned as city officials scrambled to navigate the process for council on Wednesday debating the budget he proposed under strong-mayor powers. It’s possible he will appear at council as mayor.

Some of his council allies, the Star has learned, spent the weekend trying to get signatures on a letter urging Tory not to resign at all, saying his apology was enough to get him back leading Toronto through these troubled times.

Tory himself is believed to have heard such pleas to get back to city hall but, as of Sunday, there was no sign that he was doing more than listening, even as some former allies moved behind other candidates in the nascent mayoral race.

Tory confidants are still struggling to understand what he was thinking, putting his beloved job at such obvious risk. While a famously public person, they noted, he is also intensely private, something the pandemic and its stresses seemed to exacerbate.

Several expressed feelings of betrayal, mixed with pity for Tory and fears for the woman at the centre of the scandal.

A longtime friend, his voice catching, said: “I’m really sad for him. The city is in good hands with John Tory.

“I just wish he hadn’t run for a third term. I’m crushed.”