Joe Cressy, the man who would (not) be mayor

Why one of the city’s youngest and most effective political leaders is calling it quits

It has been 629 days since the first reported case of COVID-19 in Toronto.

The number comes instantly to Joe Cressy, sitting on the back patio of a coffee shop close to city hall where the city councillor still goes to work most days as health board chair in a once-ina-lifetime pandemic.

And it’s top of mind as the 37-year-old tells two Star reporters that he does not plan to run for council in the 2022 election — not for his Spadina—Fort York seat, nor for mayor, despite his name being floated in public and political circles and a poll conducted this week for the Star by Forum shows strong name recognition against Mayor John Tory.

Though he is prominent in political chatter about Toronto’s mayoral race, now one year away, and is considered the best hope from council’s left-leaning wing, whether Tory is in the race or not, Cressy no longer wants the job.

It leaves an uncertain race for Oct. 24, 2022, with Tory not ready to reveal his intentions when asked directly by the Star, amid signs he is gearing up for at least the possibility of seeking a third term.

And it means the end — for now — of the political career of one of the youngest and most effective councillors to walk through the doors of 100 Queen St. West.

Cressy has successfully pushed for supervised injection sites, challenged some of the city’s biggest developers, joined Tory to force Premier Doug Ford to reverse public health cuts, and then reprised his unlikely left-right alliance with the mayor, and public health chief Dr. Eileen de Villa, to lead Toronto through the pandemic.

“I will not be running for mayor. I will not be running for city council. I will not be running in the provincial election or if there was a federal election. I’m leaving elected office,” Cressy said.

“The last two years have certainly affirmed that decision, based on the workload and the personal toll.”

From the time he first ran in 2014, Cressy has said he would only serve on council two fouryear terms. But in a recent interview, he said, if he was being honest, in the back of his mind he always considered a run for the mayor’s chair.

“That changed on a dime when I met my wife and we decided to have a kid.”

In the last three years, Cressy got remarried to author Grace O’Connell and became the father of now two-year-old son Jude — their first child.

The last two years have also taken a toll.

Twice, he’s had to say goodbye to O’Connell and Jude — starting with the first wave of the pandemic as a member of the city’s emergency response team, before vaccines were available and information about transmission was still spotty.

He stayed home to continue meeting daily in person with the team — medical officer of health de Villa and others were also isolated in hotels and elsewhere — while his wife and child, just several months old then, stayed with his parents for about two months.

Then, later, during the third wave when the city team was pushing its vaccination program, Cressy said he was working 18 or 20 hour days and “couldn’t be a good dad and lived apart from my family in order to put the hours in that were necessary.”

“You know, I kind of want those hours back.”

The job has also seen Cressy — who in a 2018 Toronto Life essay detailed facing anxiety and associated panic attacks — wind up going to the emergency room three times during the pandemic. He said each time he wondered if he was having a heart attack. Now he describes it as “the physical manifestation of emotional stress and pressure and the belief that that is physical.”

And so, despite acknowledging the pressure on him to run for mayor — against Tory or not — is immense, he’s no longer interested.

“It’s just not the job or the right time for me,” he said.

“You can’t live a balanced life. I can’t be the father I want to be while leading the city in the manner it deserves to be.”

Joseph Cressy was born July 10, 1984, to social activist parents Gordon Cressy and Joanne Campbell. His father was a former city councillor and Campbell was still a sitting councillor when she became the first to give birth in office — “City Hall’s first baby,” the Star declared under a photo of a beaming Campbell. Joe Cressy, as it were, has been part of council in some way since he was in utero.

Cressy’s longtime best friend, Coun. Mike Layton, loves to show a video of Cressy’s father, holding young Joe dressed in baby blue, being interviewed by an off-screen Citytv reporter.

Mid-interview, Joe, now known amongst the press gallery for giving flawless sound bites, leans in to take what looks like a bite out of the wind screen on the reporter’s microphone. The elder Cressy can’t help laughing as he tries to pry bits of foam out of his son’s mouth. On a second attempt at the clip, Joe goes fists first, yanking the mic into his mouth.

Following his parents’ vocal lead, he championed anti-war causes and environmental issues in his teens. He met federal NDP leadership hopeful Jack Layton at a protest as a youth organizer and went to intern for him at 18 years old.

He said he learned from Layton how principled activism could lead to principled coalition building.

“Jack had this ability to build bridges to bring people from activism inside to create change here.”

It was later, when he and Mike Layton, Jack’s son, were both campaigning on water issues, that they reconnected and in 2010, Cressy was campaign manager for the younger Layton’s successful council run.

Four years later, Cressy himself looked to step into the political fold and challenged Liberal Adam Vaughan, a former city councillor, to represent the Spadina—Fort York area in Parliament during a 2014 federal byelection. He lost by more than 6,700 votes.

He quickly turned around to mount a campaign municipally for the council seat Vaughan had vacated. This time, against 21 other candidates in an open race, he won by a landslide.

Since then, Cressy has led the charge on allowing supervised consumption sites, where drug users can safely consume illegal substances under the watchful eye of a trained nurse.

Cressy recalls it as controversial, “if not toxic,” at the time, but he teamed with Layton’s office to rally support on council and in community members who had overseen illegal safeinjection sites in parks.

Nearly four years ago, in November 2017, the city itself, through Toronto Public Health, opened the first legal site on Victoria Street — only the second city in Canada to do so after Vancouver. Today, there are nine funded sites across the city.

Again partnering with Layton, Cressy pushed permanent bike lanes on Bloor Street, which has led to expansions and pilots in other areas like Danforth Avenue.

He too was at the heart of approving the King Street pilot that prioritized streetcars over car traffic.

And when the community and arts entrepreneurial hub at 401 Richmond St. faced closure over excessive property taxes, Cressy helped start a wave of new tax classes to keep those and other types of businesses afloat.

He has also faced significant community blowback in a ward that has both incredibly wealthy pockets and severe issues of homelessness and poverty.

His time in office has seen more vocal residents decrying both the locations of new homeless shelters in his ward and their speed of opening and, more recently, his and other council members’ lack of public statements about the forcible clearing of homeless encampments, such as the one in Trinity Bellwoods Park.

Ceta Ramkhalawansingh, a longtime city hall bureaucrat and community builder who briefly served as the area councillor when Vaughan resigned, said the residents of the ward have incredible expectations of their councillor.

“Joe listened to the residents,” she said. “He listened to the residents’ associations. He took his lead from them certainly in terms of fighting the big development and the big institutions in the neighbourhood.”

Cressy’s work over the past seven years has led to some unlikely friendships, Tory’s chief among them.

Cressy recalls sitting next to the mayor on Remembrance Day 2014 — weeks after they were both first elected to council — talking about how former Ontario PC premier Bill Davis and NDP opposition leader Stephen Lewis worked together.

“Stephen Lewis is a political mentor of mine, I was a director of the Stephen Lewis Foundation. Bill Davis was a personal and political mentor of John Tory’s,” Cressy said. “And we had a conversation about how Bill Davis and Stephen Lewis governed together and fought the good fight against each other and then found ways to bring progress when they agreed.”

Of that relationship and his with Tory, he said: “You can disagree vehemently and still deeply respect each other.”

Like that pair, Cressy said he and Tory come from similar circles but with different approaches.

Both wealthy and privileged, Cressy’s father Gordon Cressy would caddy for Tory’s father, John Tory Sr., in his Saturday morning group at the Rosedale Golf Club.

In the late 1960s, Gordon Cressy showed up to watch his brother compete in the club championship with a friend who was Black. When his friend was asked to leave, Cressy resigned his family membership in protest. Tory’s dad was later the person who nominated and fought for the first non-Christian board member, Cressy remembered.

“The Cressys left to go storm the Bastille and the Torys stayed on the inside to bring about change over the long term. We come from different political traditions but with some similar foundational values.”

The younger Cressy and Tory haven’t always agreed.

“Nobody will be surprised to hear that, you know, over seven years, the mayor and I have had disagreements and voted differently. I wanted to tear down the Gardiner. He wanted to keep it up. I wanted to raise taxes on luxury homes. And he wanted to keep the taxes the same. I wanted to reallocate the police budget and he didn’t at the time.”

But two years ago at the beginning of the pandemic, he said the two had a “heart-to-heart” and agreed to govern as a “wartime cabinet.” They’ve spent most days in constant communication since then.

“We’ve also at all times found ways to work together because that’s what city politics demands.”

In an interview, Tory said Cressy has been “a really strong partner.”

“In an emergency situation, where the demands were as extraordinary as anything I’ve ever seen, he was there at the table as a true partner. I appreciate that, as should the people of Toronto,” the mayor said.

“It’s to his credit and should be taken note of by those who might take advantage of those talents in areas of life outside of politics. I suspect that if he leaves politics, as he says he’s going to, that he’ll be back.”

Then there’s the Ford family dynasty. Cressy has a good rapport with Michael Ford, including attending a Super Bowl party together. It will surprise many, including at city hall and Queen’s Park, that Cressy has a good relationship with Michael’s uncle, Premier Doug Ford.

“Despite what people might think, Joe and I have had a good working relationship for many years,” Ford said in an emailed statement. “He’s been a great partner throughout the pandemic and a true champion for the people of Toronto. I wish him the very best in his next chapter of life.”

As for Layton, Cressy chokes up talking about his best friend.

Before the pandemic, Cressy, then a bachelor, often ate reheated meals brought to city hall by Layton, a foodie. Layton’s

“You can’t live a balanced life. I can’t be the father I want to be while leading the city in the manner it deserves to be.”

JOE CRESSY

ON BEING MAYOR

one-man food train has continued.

“In the first wave, when I was living alone, he would make me dinner every single night,” Cressy said.

“I would leave city hall, where nine of us were working, at whatever ungodly hour, show up at his and his garage and he would have a Tupperware of food for me … And then I would bring the Tupperware back the next day, and he did that for months.”

Of Layton, he said: “He is genuinely the nicest person you will ever meet.”

Layton, also now a father with two small daughters at home and himself on the list of potential mayoral candidates, credited Cressy with convincing him to run for municipal office. Of the food, he said it was an obvious way to help. “He’s family. You’ve gotta feed family.”

He remembered the times Cressy would stay to eat — placing circles out in the alley next to his house so they could sit safely apart and talk about their days.

“It was a lonely time, but I think we both found value in it.”

Layton said he cried when they were first able to hug again.

When it comes to the end of his political career, Cressy said he doesn’t think people should close the door on anything — “I would never say never.”

Cressy said he isn’t sure what he’ll do next, but he’d like to continue serving the public at the “intersection of health and social and community services.” He name-dropped the YMCA and United Way as dream employers.

Both his parents left their council seats after two terms, he noted.

“And they both went on to contribute greatly to this city and I got to see them a lot as a kid.”

He said he himself is guided by a Quaker saying that he summed up as: “Do all the good you can for as long as you can for as many people as you can.”

As a new dad himself, he championed the idea councillors should be allowed paternity leave. That and other changes are needed to entice more diverse candidates to a city hall that is, he said, older, whiter and more male than Toronto itself. But no change would, at the moment, tempt him to run again for council or the all-consuming mayor’s job.

As for his immediate plans for his first day of no longer being a politician?

“Probably go to the playground with Jude.”