When Jennifer Keesmaat was named Toronto’s chief planner, her Grade 8 teacher called to congratulate her — and remind her of an unusual speech she gave in class.

The topic was sidewalks and the role they play in our lives. It was a presentation she had long forgotten.

“Why was I talking about that at that age? I don’t know,” Keesmaat says in an interview. “You post-rationalize. I walked to school. It was a long walk and I loved that walk … Obviously it made an impact on me.”

A walkable city, more bicycle paths, midrise developments, evidence-based investments in transit, improved laneways and sidewalks — they’re all concepts that Keesmaat champions. Loudly.

Not your typical bureaucrat, Keesmaat blogs, tweets prolifically (more than 11,000 tweets and over 28,000 followers), hosts roundtables and delivers TED talks.

Keesmaat, 45, has established a reputation as someone unafraid to state her views — even if they conflict with those of her ultimate boss, Mayor John Tory. Last spring, in front of members of the Urban Land Institute, a group of experts on planning and development in Toronto, Keesmaat twice interrupted Tory to correct him as he spoke about her planning department budget. (Tory says they were both correct).

Then in the summer, her outspokenness got her into hot water with the mayor’s office. She opposed Tory’s vision for the future of the Gardiner Expressway, and ended up having her wrists slapped for public statements and tweets where she seemed to be actively lobbying for an alternative Gardiner plan. In the end Tory’s vision won city council approval.

Tory says he and Keesmaat got off to a rocky start, but now their professional relationship is “on the up.” The mayor calls her a “very imaginative, provocative, smart resource” he can use for ideas.

“She’s one of the best hopes we have to lead the way,” Tory says in an interview.

At the beginning of this year she earned praise for proposing a compromise for transit in Scarborough. It pleased advocates of a subway, offering a one-stop extension from the Bloor-Danforth line to Scarborough’s city centre. It preserves some of Tory’s SmartTrack rail plan, and calls for light rail transit lines that connect underserved neighbourhoods in Toronto — a plan Tory said makes “huge strides.”

Her detractors charge that she craves the limelight and is burnishing her image for a future bid at political office — a claim she adamantly denies.

Keesmaat says she wants to foster a climate in which residents are engaged in making neighbourhoods better and improving the city as a whole.

“A city isn’t something that happens to you. You make choices every day that shape and make your city,” she said during a TED talk at York University shortly after being named chief planner.

Some say Keesmaat’s family history provides clues to her penchant for speaking out — what one observer calls her rebellious streak.

Her Dutch relatives played major roles in the resistance movement after the Nazis invaded the Netherlands in 1940. Her grandfather’s brother was shot dead for participating in the struggle.

Keesmaat has said her family history made her realize she has to “stand up and stand out.”

First moves

It’s a cold February morning as Jennifer Rachel Keesmaat gets off the elevator at city hall and heads into the planning department.

She’s confident and sharply dressed in her brown blazer, white dress shirt and black slacks. On this day she eschews her trademark high heels for winter boots — it’s snowing. She’s photogenic and fit, often cycling to work from the Yonge and Eglinton area home she shares with her husband, Tom Freeman, 43, daughter Alexandra, 15, and son Luis, 10.

Her office has papers everywhere: TTC summaries, planning reports and other documents spread across her desks or pinned to the wall.

“My office isn’t usually this messy, but I’ve been busy these days,” she says.

She and her staff have been working intently to help develop new plans for transit in Toronto, including long-term goals.

They’re part of what Keesmaat calls the “motherlode” of transit, plans that if funded by all three levels of government, would see miles of new rapid transit lines. The plans incorporate several proposed provincial and city directed projects including SmartTrack, a priority for Tory, and a downtown relief subway line — considered more of a priority by Keesmaat and TTC leadership. (A recent ridership study found both lines are needed to relieve congestion on the Yonge subway.)

Council last week endorsed several new lines, including an LRT along Eglinton Ave. E. in Scarborough and the first leg of a downtown relief subway line to run along Queen St. E.

The ability to move around one’s city — especially on foot or by transit — is one of Keesmaat’s priorities. It’s a theme she touches on in a TED talk in 2012.

In the talk, called “Walk to School” (delivered before taking on her chief planner role), Keesmaat points out that studies have shown that as walking has decreased, obesity, including childhood obesity, has increased.

As a child, she made her 1.5-kilometre trek on foot to Calvin Christian School, an independent Dutch school in Hamilton.

What type of pupil was she?

“I was active, outspoken,” Keesmaat says in an interview. “I got bored fast. I need more than one thing happening at once. A had a lot of detentions for talking in class or not having my homework done. I was an average student. It wasn’t until I got to senior grades that I started to excel.”

In high school she found an outlet for all that pent-up energy — sports. Aside from playing and coaching basketball, she played volleyball and ran track and cross-country.

She was active at home, too. She has three sisters — Sylvia, Valerie and the youngest, Elizabeth. The three eldest rode their bicycles everywhere and plugged up a local culvert every autumn so the field would flood, later giving them a free place to skate.

Keesmaat’s father, Leonard, a builder and craftsman, treated them as he would have treated sons, recalls Sylvia Keesmaat, 50, a biblical scholar and professor at the University of Toronto.

“He took us fishing and camping,” Sylvia says. “He had us put up the tents and had us handle our own fishing tackle. That created a certain confidence in all of us.”

Whether outdoors or around the dinner table, Sylvia recalls her sister Jennifer’s “incredible dramatic flair, passion and exciting detail” when it came to storytelling. And their mother, Irene, an artist, encouraged Jennifer’s interest in public speaking.

Beginning when Keesmaat was about 9 her mother enrolled her in the Kiwanis Music Festival, where she participated in public speaking and storytelling competitions over the next few years.

Her mother was her coach.

“I was fearless in terms of getting up in front of an audience and speaking publicly, in part because my mom just pushed me out there and I went and did it. She didn’t do it with my other sisters; she just did it with me.”

Roots in the Resistance

“I see how the first light of the morning comes through the high window pane. My God, please make my dying light. I failed though I did try, like any other could have done. Please grant me your mercy so that I will meet my death as a man when I face the barrel of the gun.”

These are translated lines from the late Dutch poet Jan Campert’s “De Achttien Dooden” (“The 18 Dead”), an ode to 18 resistance fighters betrayed, tortured and ultimately forced to dig their own graves before being executed by the Nazis in March 1941, near The Hague.

One of the 18 was Leendert Keesmaat.

He was the brother of Jennifer’s grandfather, Arie. The two and another brother, Wim, were imprisoned for resisting the occupation in May 1940, though Wim and Arie were spared.

After the war Arie brought his family to Canada.

“The Canadians liberated Holland — for this reason my grandfather was enamoured with Canada,” Jennifer says.

Her late grandfather never recovered from guilt over the fact his brother was killed. Jennifer’s father is named after his slain uncle.

“I’m very conscious of my family history and culture,” Keesmaat says. “I do think it informs my values.

“I was raised on stories about the role my family played in the resistance.”

She learned more details about this chapter in her family history in 2014 when Anne van Leeuwen, consul general of the Netherlands, based in Toronto, showed her an article from a Dutch publication.

It’s this past that explains part of why Keesmaat isn’t afraid to be forceful, van Leeuwen argues.

“It’s not anarchistic, but rebellious. (It’s about saying) ‘if I have an opinion, if I think this is the right thing to do, I’ll do it, no matter what authorities think of it.’ That’s exactly what made heroes during the Second World War,” van Leeuwen says.

Keesmaat’s penchant for speaking out and her high visibility have left her open to accusations she’s laying the groundwork for a future run at politics.

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“I think she has political aspirations and I wish her the best of luck,” says Councillor Jim Karygiannis (Ward 39, Scarborough-Agincourt). “But while you’re working for the city you’ve got to be working for the city.”

But supporters say her activist approach has given the chief planner’s role a much-needed reboot that has energized Toronto.

“From my perspective she’s done exactly what we’d hoped she would do,” says Liberal MPP Peter Milczyn (Etobicoke-Lakeshore), the ex-Toronto councillor and former chair of planning and growth, who was on a three-person panel that hired Keesmaat for the city in September 2012. “She has taken on a real leadership role. She has promoted the cause of city building and good urban planning across the city, to the media, to the public and certainly (city) council.”

Keesmaat, who worked years ago as an assistant in Councillor Joe Mihevc’s office and for former councillor Jane Pitfield, says the professional profile she maintains isn’t at all about future political aspirations. Rather, she has a strong desire to make planning and city building as “transparent as possible” by catering to members of the public who have a “real thirst” for what’s going on in Toronto.

“There has been an energizing aspect of her being at city hall,” says Antonio Gomez-Palacio, with whom she formed Office for Urbanism, an urban planning and design firm in Toronto.

“It has made the public truly feel their input is meaningful and they have an avenue to be part of the city-building conversation.”

The Jacobs effect

Keesmaat became enamoured with planning after reading Jane Jacobs’ 1961 book The Death and Life of Great American Cities, which analyzes urban planning.

In 1993 Keesmaat graduated from the University of Western Ontario with a double major in English and philosophy, and married her husband. (They wedded about two years after meeting at a summer camp in Muskoka, where at one point he turned to her, a person he barely knew, and said, “I’m going to marry you.”) She gave up on the idea of a law career after a few “tedious” summers filing papers in her uncle’s law firm.

Inspired by Jacobs, Keesmaat enrolled at York University’s environmental studies program in 1997 and studied planning. She developed tight bonds with some students in the program — ties that remain to this day — including Gomez-Palacio, a close friend as well as future business partner.

Her friends in the program were drawn together in part because they share a liberal sensibility, Keesmaat says.

“We all had a shared intuition and a shared series of questions we were dealing with around community, individual and social well-being, and the (notion) that it was through cities and the urban environment that we could deal with these questions,” Gomez-Palacio says.

After securing their master’s degrees in planning, Keesmaat and Gomez-Palacio founded the Office for Urbanism in 2003. (Harold Madi, now Toronto’s director of urban design, was a third founder.) In 2004 the firm made a major splash — it landed the contract for the master plan for the revitalization of Union Station.

“That was a huge coup,” Keesmaat says. “We worked around the clock on it.”

Office for Urbanism also authored master plans for downtown Halifax; Moncton, N.B.; Regina; and Saskatoon, as well as studies for Toronto including Bloor St. W., Queen St. W. and Yorkville Ave.

In 2010 the company merged with three other firms to form Dialog, whose services include urban planning, design and architecture. Gomez-Palacio is a principal with the firm.

Keesmaat moved on from Dialog to become Toronto’s chief planner, where her salary, according to public records, was $240,041.45 in 2015.

Rubbing some the wrong way

In her recently launched blog, Own Your City, Keesmaat references a speech she gave last fall at a conference of the Ontario Professional Planners Institute, where she urged that planners assert their roles as experts and not let pressure and influence from their political masters sway them from doing so.

It’s a line of thinking that has brought her into conflict with councillors like Jim Karygiannis, who believe the chief planner and any senior staff with the city should be taking their marching orders from councillors.

“You’re there at council’s direction,” he says.

She does have testy, thin-skinned moments. For example, during the controversy last summer over her public statements on the Gardiner, a CP24 reporter asked Keesmaat if she’d been muzzled by the mayor’s office.

“Sorry, but I’m not talking about this on the air. Sorry, could you just not roll the camera?” Keesmaat said, and then put her hand over the lens. Keesmaat told the reporter: “I’m offended because you’ve monopolized me as I’m running into a meeting.”

She later apologized to the camera operator, adding she didn’t have media training.

On his rough start with Keesmaat, Tory told the Star that as the former CEO at Rogers, he was more accustomed to being the head of a corporation where you would almost never find vice-presidents out giving a speech that challenged the orthodoxy of how the company had done business over time, or taking a position that was different from the CEO’s.

“I came to realize a couple things: First of all this isn’t a corporation; it’s the city. And secondly, that particular position over time has been one where by definition it was almost expected the city planner would be looking to the future.”

Councillor Shelley Carroll was initially critical of Keesmaat — she suggested the planner seemed to be engaged in a “branding” exercise — but has since come around, too.

Carroll says when Keesmaat first came into the job she expected the chief planner to be more hands-on in planning projects in Carroll’s North York ward. But planning staff under Keesmaat do that work, in a manner Carroll describes as very smooth.

That process now leaves Keesmaat to focus on the broader picture across the city, Carroll says.

Two controversies at a glance

Often outspoken in her tweets, public statements and interviews, Jennifer Keesmaat has been at the centre of controversy on a few occasions:

1) The tweet: According to published reports, in November 2012, just two months after starting as chief planner, Jennifer Keesmaat sent out the following tweet (since deleted) during a city council meeting break: “Now that half of council is considering running for Mayor, the speeches at council are … insufferable. Did I say that out loud?”

The backstory: Then mayor Rob Ford was facing possible removal from office amid conflict-of-interest charges after he spoke and voted at council in early 2012 on whether he should be forced to repay $3,150 to lobbyists and a company from which he had accepted donations to his football foundation.

The reaction: Keesmaat later told a reporter the word insufferable “probably crossed a line” and that she has “deep” respect for councillors when they speak. She said the tweet was meant to be funny. Councillor Jim Karygiannis says, looking back at the incident, Keesmaat’s poke at councillors was “distasteful,” adding, “You don’t criticize the people you work for.” Noting that Keesmaat admitted she’d made an error with the tweet, city of Toronto spokesperson Jackie DeSouza said at the time city staff should use good judgment on social media.

2) The statement: Last spring and summer, Keesmaat said taking down the eastern section of the Gardiner and replacing it with a grand eight-lane boulevard is the best choice for the city. She also tweeted her support for the idea. At the time she said her position is based on her “professional expertise” and analysis by her planning staff.

The backstory: After appearing at an international conference for landscape architects in May 2015 in Toronto, Keesmaat told reporters the grand boulevard could weave together the waterfront with the rest of the city and open new parcels for development. But concerned about traffic, Tory backed a costlier hybrid option, which would retain most of the Gardiner. (This week, council approved a $1-billion version of the hybrid plan.)

The reaction: Tory told reporters in June that while the chief planner and other senior staff have the right and duty to express their opinions publicly, “I think there’s a line that has to be drawn between what a public servant on any issue — not just the Gardiner — should be saying in terms of debating politicians.” Later the mayor’s chief spokesperson confirmed Tory, his staff and another senior city official met Keesmaat over her tweets and public comments. During this time, according to reports, the city of Vancouver tried unsuccessfully to poach Keesmaat.

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