Troublemaker: Why Jennifer Keesmaat may be exactly what Toronto needs right now

The Frederick G. Gardiner Expressway runs for 18 kilometres. From the sky, it’s a snaking schism dividing the waterfront from the rest of the city. On its surface, it’s a hellscape of decrepitude that occasionally drops chunks of concrete onto Lake Shore Boulevard below. In its mass, the Gardiner represents everything that’s wrong with Toronto right now: the gap between the core and the suburbs, our stubborn emphasis on cars over public transit, the bloodthirsty grappling at city hall.

And yet when Jennifer Keesmaat, Toronto’s irrepressibly idealistic chief planner, announced that it’s time to tear down the eastern tail, the city was stunned. She was speaking onstage in May at a conference at U of T’s Isabel Bader Theatre with the former chief planner Paul Bedford, himself a loudmouth Gardiner abolitionist. Keesmaat wore a black blazer, grey slacks and vertiginous nude pumps. She looked crisp and strategically hip, her wheaty bob defiantly kicking up at the ends, like the swoosh of a check mark. After more than two years of carefully couching the Gardiner question, she finally came out and said it. “We have an opportunity to create a brand new streetscape in our city by taking down this antiquated, dark, crumbling infrastructure and reinvesting in the public realm,” she told Bedford and a room of feverishly tweeting urban planners. “It’s clear removing is in the best interest of the long-term vision, as articulated in our official plan,” she later told the Toronto Star.

It was Keesmaat’s “I am Spartacus” moment: in supporting the demolition of the Gardiner East, she was facing off against John Tory. The mayor had already championed a hybrid plan that would involve rebuilding the elevated deck, adding new on-off ramps and streamlining Lake Shore Boulevard east of the Don River, at a cost of $919 million. Removing that eastern portion, on the other hand, would only cost $416 million, leaving a half-billion in change to underwrite public transit and infrastructure, and generating an estimated $150 million in potential land sale profits. The moment the words left Keesmaat’s mouth, Twitter’s wonkish #topoli squadron erupted in ebullient praise. Urbanist demigods Richard Florida and Ken Greenberg also tweeted their support, lauding Keesmaat’s conviction.

Publicly, Tory handled Keesmaat’s statement with WASPy diplomacy. “I’ve set out my own position and she’s set out hers,” he commented. “She’s perfectly entitled to do that as the city’s chief planner.” Three days later, the pair plastered on smiles and shared pancake-flipping duties at a city hall breakfast. But Keesmaat kept picking at the scab, retweeting her supporters and reiterating her position on social media. “Creating a ‘grand boulevard’ and a pedestrian promenade unlocks 12 acres for redevelopment and costs half a billion less,” she tweeted. Eventually Tory had enough and pulled Keesmaat into a meeting where he basically told her to zip it. “The mayor has said it is perfectly appropriate for staff to make their opinions public, as Ms. Keesmaat has done,” wrote his communications chief, Amanda Galbraith, in a statement. “It is not appropriate for city staff to campaign against councillors or the mayor on social media or through other public platforms.” Keesmaat counters that she never campaigned. “I stated an opinion,” she says simply. Tory’s hybrid plan was victorious at council, but the Twitter contingent continued to rally behind Keesmaat—the week of the council vote, her fans even started a popular #ThankYouJen hashtag. “There’s a very good chance they’ll fire her for not toeing the party line,” one ex–city staffer told me. “But if they don’t, it will be a watershed moment that empowers city planning to speak openly about critical issues.” And, of course, they didn’t.

Before Jennifer Keesmaat was running the show, Toronto’s planning department tended to follow council’s lead. The office was understaffed and dispirited. City employees lacked the resources to undertake studies, which meant their approach was often ad hoc instead of prescient. Worse than that, they could be deferential and excessively nonpartisan, letting decisions about development and infrastructure fall to the whims of others. “City staff were rendered irrelevant by Lastman, professionalized into silence by Miller and scarred into silence by Ford,” says Adam Vaughan, the former Trinity-Spadina councillor and current Liberal MP. The result was sluggish transit and poor land use, pandering politicians and vulpine builders, glassy downtown growth and not enough infrastructure to support it.

When Keesmaat arrived at city hall in July 2012, she quickly established herself as an evangelical chief planner. She uses every resource at her disposal to disseminate her message, a fantasia of densification, infrastructure, transit expansion and green space. She delivers rousing homilies and catapults planning into the centre of the urban discourse—much to the chagrin of some councillors, who believe it’s the job of city staff to silently toil away in the turrets, and developers, who aren’t used to asking twice for what they want. She heralds the kind of tomorrowland we haven’t heard about since the days of Jane Jacobs. Not only does Keesmaat plan to ensure Toronto gets there, but she’s intent on being the one who makes it happen—no matter who she has to piss off along the way.

Toronto’s chief planner rides a virgin-white, seven-speed Norco with a fawn leather saddle. It’s her gleaming steed that whirls her from BIA meetings in the Junction to family excursions in the Don Valley to council meetings at city hall. (She parks it in her office, having had a previous bike stolen from the petty crime hub that is the underground garage.) Beyond its functional value, Keesmaat’s bike is an ideological token, a piece of personal branding that spins her mantras of livability, walkability and sustainability with every turn of the spokes.

Keesmaat lives in a narrow red-brick detached house near Yonge and Eglinton with her gregarious, marble-jawed husband, Tom Freeman, who looks like a contestant on The Bachelorette. He runs FH Hospitality, a company that sells high-end fixtures and furniture to hotels like the Four Seasons and the Royal York. They have two kids—15-year-old Alexandra and nine-year-old Luis—and together they form a quartet of athletic keeners: they take family bike rides and ski trips, Alexandra skis and rows competitively, and Luis is a champion snowboarder. To accommodate Keesmaat’s schedule, Freeman works from home and does most of the cooking, organizing and child shepherding. It scans as an idyllic life: once a week they have dinner with other families on the block. “I know my neighbours,” Keesmaat gloats. “You know how? I walk. I rarely get in a car on weekends.”

Freeman describes her as a doting mom who cuddles in bed with the kids each night, recapping their days. She takes every opportunity to show off photos of the family on her iPad and proudly tells me that this summer she and Alexandra will be co-writing a YA novel set at city hall. But she’s also a hard-ass: the only TV shows allowed in the house are educational, like The Agenda (and the occasional guilty-pleasure episode of The Voice). As a matter of principle, she insists that her kids walk to school. A few months before she started as chief planner, she became known for a TED talk in which she reflected on the benefits of the morning hike and about trusting the city to be safe enough for her kids. “I’m not going to raise my children with choices made in fear,” she tells me. “Whenever I’ve confronted an option between hope and despair, I’ve chosen hope. We can build a better world. Societies can change their course.”

You can tell she believes her own hype. She possesses the indefatigable cheer of a camp counsellor or a children’s entertainer or Anne Hathaway, peppering her speech with inspirational aphorisms and teachable moments. When she speaks, she stares at you with a hammering green gaze, her irises luminescing like light sabres. When she gets excited about something—bike lanes, employment lands, mid-rise densification—she practically convulses at you, thrusting her body forward from across the coffee table with spurts of kinetic vim. When she talks about social issues, like affordable housing and police carding, she gets choked up with what appear to be real tears. Keesmaat’s hands are constantly moving, stretching invisible buildings up to the sky, swathing imaginary plots of land, hopping across the utopian city of tomorrow only she can see. Spending time in her orbit is by turns seductive and grating, exhilarating and exhausting.

To hear Keesmaat tell her life story, it seems as if every moment was a fateful plot point on her path toward city building. She’s the third of four sisters, born in 1970 in Hamilton to Leonard and Irene, who both came to Canada from Holland as young children. Leonard was a craftsman and builder who worked on high-rise developments and university projects. Irene was an art teacher who fired ceramics in a basement kiln. Her parents figure into the grand narrative (“I’ve always been surrounded by creativity”), so does her family history in the Dutch resistance movement (“Those stories made me realize I have to stand up and stand out”), and so too does her childhood bike (“It was my instrument of freedom”). In high school, she juggled the basketball team and competitive track and field while maintaining an A average. During university, she planted trees in the Northern Ontario bush. When she enrolled at Western for undergrad in 1989, she planned to pursue a career as a phys-ed teacher—which probably would have been a good fit—but later shifted her ambitions to law, spending summers filing in her uncle’s Hamilton firm.

After her second year at Western, she took a job at Muskoka Woods summer camp on Lake Rosseau, where she met Freeman, then an 18-year-old high school football player from Etobicoke whose Richview Collegiate Saints used to play against Rob Ford’s Scarlett Heights Raiders. Their romance was charmed: Keesmaat was a basketball instructor, Freeman taught water-skiing. That summer, he learned basketball just to woo her. “She was smart, articulate, funny, warm, beautiful,” he says. “The whole package.” Keesmaat says she was too embarrassed by her high school boy toy to tell anyone they were dating for a year. When he was 21 and she was 24, they married.

Soon after the wedding, Keesmaat and Freeman moved to Vancouver, where he’d landed a job as a youth director at an Anglican church and she worked as a residence don at UBC. Ever the starry idealists, they quickly became embroiled in the politics of the Downtown Eastside; she organized a speaker series to raise awareness and fight gentrification. The rest of the time, of course, Keesmaat was on her bike. “When I was riding, I became fascinated with the relationship between built form and land use. It made me realize that a city is an art, something evolving and dynamic,” she says. One night, the couple biked to a party, where Keesmaat got into a conversation about her newfound obsession with city building. “The guy asked me, ‘Are you a planner?’ and I was like, ‘Uh, what’s a planner?’ So I went home and read Jane Jacobs,” she explains, her voice lowering into a reverential growl. “As soon as I cracked open The Death and Life of Great American Cities, that was it. I was home.”

After dabbling in a few planning courses at UBC, Keesmaat decided she was serious. In the late ’90s, she and Freeman moved back to Toronto, where she enrolled in the environmental studies and planning graduate program at York. Planning is a Frankenmonster of a profession, each project a pastiche of architecture, engineering, infrastructure and politics. A planner creates policies and regulations, but also needs to know how they translate into real buildings, how to apply them and when to break the rules. At York, Keesmaat studied planning law, social planning and governance. She learned about transit modelling and environmental assessments and heritage regeneration. Clairvoyantly, she wrote her master’s thesis on the intersection of politics and planning, during which time she worked as an assistant in councillor Joe Mihevc’s office and got her first taste of the infighting at city council. “Over here,” she says, hands flying like a baton twirler’s, “is what we know about creating a sustainable and livable city. Over here is where decisions are being made. We knew what good planning looked like, yet we were making those bad decisions anyway.”

In 2003, she teamed up with Antonio Gómez-Palacio, a fellow York planning alum, and Harold Madi, now her director of design at the city, to found the Office for Urbanism, a tiny consulting firm at Yonge and Richmond. The first project they won was the Union Station master plan. During months of public consultations, some stakeholders proposed they transform it into a train station that was also a mall. Others suggested a train station that was also a condo tower. Keesmaat and her team opted for something so obvious it seemed revolutionary: a train station that was just a train station. It was as important for people to get around Union as it was to get in and out, so they focused on internal navigation, adding new concourses, retrofitting unused storage spaces and tunnels into corridors, and creating dozens of new entries and exits to transform the shell of the building into something breezy and porous.

Over the next several years, cities across Canada retained Keesmaat to direct redevelopment, including Moncton, Iqaluit, Saskatoon and Belleville. In Regina, where there were three parking spots for every car, she planned for denser downtown housing—lofts, townhouses, one-bedroom condos—in the core, to lure urbanist boomers who might otherwise flee for Toronto or Montreal. She reimagined the core in Halifax, setting specific allowable heights in various neighbourho0ds, streamlining the process for developers to get approval on tall buildings and adding new pedestrian infrastructure. And here in Toronto, she was responsible for the city’s first commercial heritage conservation district on Queen West, which immunized the stretch of Queen between University and Bathurst against the blitz of glass towers that had just started to proliferate downtown. Within a few years, the Office of Urbanism merged with several other firms to form Dialog, a cross-country planning and design studio. Keesmaat co-led the planning division.

Toronto, meanwhile, found itself plannerless in 2012, after Gary Wright, the amiable bureaucrat who’d held the job for four years, announced his retirement. A city hiring committee wooed Brent Toderian, who’d recently been fired as Vancouver’s chief planner after a series of rumoured disputes with city manager Penny Ballem. He’d soured on the job when Rob Ford orchestrated the dismissal of TTC general manager Gary Webster for disagreeing with him on transit strategy, but decided to sit through an interview anyway. While he was in town, Toderian watched council’s streetcars versus subways debate from his hotel room—the one where Rob Ford bellowed “subways subways subways” for 10 minutes, launching a thousand GIFs. Toderian was on a plane out of Pearson the next day. Rollin Stanley, a 20-year veteran staffer at city hall, turned down the opportunity to interview, instead accepting the chief gig in Calgary. He cited Toronto’s narrow-minded council as the primary turnoff.

Eventually, the search landed on Keesmaat, who claims she initially had no interest either. “I said, you’ve got the wrong person. I’m an entrepreneur, not a bureaucrat.” Peter Milczyn, an Etobicoke councillor turned Liberal MPP, was chair of the hiring committee. He claims, possibly with the benefit of hindsight, that she was exactly who the city needed: someone from outside the musty echo chamber that was city hall. At $217,000, the chief planner’s salary constituted a 40 per cent pay cut for Keesmaat. But her ambition got the better of her. She started imagining the influence she’d wield, the opportunity she’d have to sculpt the city. It was too enticing to resist. So she sold her stake in Dialog.

“We had other competent candidates, but we didn’t want someone who would just be competent,” Milczyn says. “We wanted someone who would be a tough leader on planning, on growth, on the future of cities. Someone who could articulate a vision for Toronto and how it would evolve.” Keesmaat could handle the planning side—she’d created dozens of master plans, and preached about density to suburbanites in Regina and Lethbridge; she knew the names of city councillors and residents’ association presidents all over Canada. But nothing could have prepared her for the shambolic bell jar that was Toronto City Hall.

Keesmaat assumed the position in September of 2012; keener that she is, she came into city hall every day in August to read files and meet with staff. Her first PR hiccup came during her first week on the job, when she launched ownyourcity.ca, her official blog. She wrote a mission statement listing all the things she loves about Toronto—and all the things she doesn’t. It read like Keesmaat’s State of the Union. “We drive in traffic chaos. We cannot be complacent about affordable housing. We commute on bike lanes that are sorely insufficient. We squeeze into subway cars that truly cannot contain another soul. Too often, our streets, squares and parks are overused and poorly maintained.” Within an hour, Milczyn was in her office, telling her that some councillors were complaining about the blog. “She was too free with her opinions,” he explains. Wrist slapped and ego bruised, she didn’t post again for three months.

Instead, she gave dozens of interviews blazoning her priorities—transportation planning, pedestrian infrastructure, spreading the wealth of densification. She criticized the way councillors use Section 37 of the Planning Act, extracting community benefits from developers in exchange for exceeding height and density limits (it implicates them in a conflict of interest, she claimed). She travelled to cities outside Canada and gave speeches under the Toronto banner. At a Board of Trade meeting, she complained about the politicized squabbles at city hall. Most of all, she tweeted. She tweeted between mouthfuls, on developer visits, at night while she couldn’t sleep. She tweeted paeans to bike lanes and green roofs, and sombre warnings about podium heights and sidewalk setbacks. And one day in November 2012, during a council meeting, she tweeted: “Now that half of council is considering running for mayor, the speeches at council are….insufferable. Did I say that out loud?” She immediately faced the fury of councillors, who weren’t used to snarky, outspoken bureaucrats. “She came into city hall with a lot of naiveté. I don’t think she thought she was going to make it,” says ex–budget chief Mike Del Grande, who faced off against Keesmaat over budget disputes. “The culture at city hall is that staff are there to cater, not to be catered to. I’d often hear councillors saying she hadn’t returned their call, then see that she’d been Twittering instead of doing what she was supposed to.”

Keesmaat quickly acquired a Twitter nemesis: Denzil Minnan-Wong, the impish, right-tilting deputy mayor who vociferously protects his constituents’ right to suburban lawns and eight-lane highways. At every opportunity, he lacerated Keesmaat’s urbanist utopianism. When she tweeted about the importance of infrastructure, he compared it to a Deep Thought by Jack Handey. When she lauded proposed improvements to bus networks, he goaded her about how voters would pay for the increased service. And when she estimated that the proposed Downtown Relief Line would take up to 15 years to build, he questioned her expertise. “Chief planner estimating construction time of subway like medical officer of health opining on best way to fill potholes,” he said. Keesmaat ignored every prod. The one-sided feud escalated over a couple of years—until Minnan-Wong discovered last April that Keesmaat had blocked him from following her tweets. “Any reason madame chief planner?” he taunted in April of this year. Keesmaat dryly tweeted back that she’d blocked him a year earlier, but he’d only just noticed. “Is it hurtful?” she asks, referring to Minnan-Wong’s Twitter trolling. “Well, sure. Is it sort of miserable for me? Yeah. I’m a person,” she says.

There’s something disconcerting in the way people talk about Keesmaat, as if she’s something to be both dismissed and contained. “Google her and see what comes up,” Freeman says, exasperated. “Jennifer Keesmaat hot, Jennifer Keesmaat sexy.” Toronto Sun readers voted her number one in their city hall hotties poll (Rob Ford won the male title). And, in particular, councillors have taken exception with her high profile in the media. “With Jennifer, you always hear about her in this article or that. She’s all about the sexy stuff, the one-liners, the 15 minutes of fame,” Mike Del Grande said. It doesn’t help that she’s photogenic and charismatic; Shelley Carroll, the councillor for Don Valley East, says Keesmaat is not only the regular subject of soft sexism at city hall, but something she calls “looksism”—that if Keesmaat were dowdy and plain, she’d have an easier time. Nick Kouvalis, adviser to the mayor, went on a Twitter tirade against Keesmaat, saying “I look forward to her name on the ballot (which I believe has been driving her public campaign to brand herself) in 2018.”

Many of the big egos around her seem threatened that she has one too, and convinced that her vanity is driving her play for the spotlight. They’re wrong. Her publicity blitz is about propagating her professional legacy, accruing public credibility, planting the seeds that will transform the city into what she wants it to be. It’s not about ego. It’s about power.

The beanstalk growth of Toronto’s downtown core is the best and worst thing ever to happen to the city. Between 2003 and 2013, there were 468 development applications comprising 118,000 units in the downtown core, many scattered through former brownfield sites in the West Don Lands near King and the DVP, the East Bayfront at the foot of Sherbourne, and the former railway lands between Spadina and Bathurst. On top of that, the core has added 6.2 million square feet of office space over the last five years. The area has morphed into a futuristic mixed-use model for urbanism, a dense and livable glass metropolis that glitters like a disco ball and places residents within walking distance of jobs, entertainment and retail. The growth rate downtown is four times that of the rest of the city. Over the past 10 years, 45,000 new residents have arrived, increasing the total population to 200,000. And it’s expected to reach 250,000 by 2031. The 17 square kilometres that comprise the area, from the CP tracks at St. Clair down to the lake, and from Bathurst to the DVP, make up just three per cent of the city’s land mass, but contribute half of Toronto’s GDP, a third of all jobs and a quarter of the city’s tax base.

For all the private wealth flowing into that chunk of land—and out of it—government has made little public investment in new infrastructure to support the mushrooming population. There’s a dearth of public spaces (dog parks, playgrounds, sidewalks). A study by the City of Toronto found that proposed developments are outpacing the current planning framework for water mains and sewer maintenance. Worst of all, more than 55 per cent of the workers downtown commute, contributing to much of the crippling, soul-sucking congestion that costs the region billions each year. While the core is feeling the strain, the density hasn’t really moved outward, leaving large swaths of the city’s infrastructure underutilized. “Planning in Toronto right now isn’t just dealing with applications and amendments and zoning bylaws,” explains Ken Greenberg, a Toronto urban planner and former chief planner for Boston. “We also need to be looking at this huge growth and what we need to accommodate it. It’s not business as usual anymore.”

The growth downtown predates Keesmaat, but she’s responsible for managing it. Her vision for Toronto is textbook New Urbanism, the kind of cultish European ideal already achieved in cities like Barcelona, Zurich and Copenhagen. She favours densification, foot traffic over cars, mixed-use land, latticed street networks and sustainable transit strategy. Lucky for her, so does Toronto’s official plan. The Bible-thick manifesto, which council adopted in 2002, sets out a Jacobsian recipe for the city’s growth plan, listing strategic goals around walkability, complete communities and comprehensive transit. When I told Keesmaat I assumed those were qualities most cities aimed for, she gently ribbed me. “Your response is very Toronto-centric,” she said. “We prioritize design, public transit, affordable housing. You’ll find most cities in Canada don’t focus on public transit in their official plan.” Keesmaat’s personal alignment with the official plan is a serendipitous synchronicity: she uses it as an ideological parachute to duck accusations that she’s too liberal. When she recommends approval on a mixed-use development that the ward’s councillor is fighting, she can prove that the area is earmarked for growth. When she rejects a proposal for being too compact, she can point to the plan’s guidelines around pedestrian infrastructure and shadow impacts. And when she comes out against the mayor on the future of the East Gardiner, she can refer to the plan’s emphasis on a rich waterfront and transit network over highways.

Beyond her buzzwords and bravado, Keesmaat is a shrewd policy-maker. Last year, she successfully fought to restore positions in the understaffed planning department so her 375-member team would have the resources to complete studies, reports and development applications. She saw through changes to the city’s fastidious tall building guidelines, which govern separation distances, podium heights and sidewalk setbacks. She’s leading studies on how to integrate the TTC, GO and planned LRT and SmartTrack lines with land use. She’s spoken out in favour of mandatory affordable housing in every high-density development project. She has been incessantly vocal about moving forward the Downtown Relief Line to alleviate traffic congestion on the Yonge-University line. And she’s kick-started a comprehensive initiative called TOCore, examining what future infrastructure needs will be and how to achieve them. Shelley Carroll admits she was once a naysayer: “but all the things I was saying I wanted her to do, she’s done. I’m Team Keesmaat now.”

Keesmaat’s most daunting challenges will be spreading density throughout the city, making the most of existing infrastructure, creating affordable housing and integrating development with new transit routes. She champions a sweeping solution to address them all: mid-rise development. In Toronto, most buildings are either squat three-floor walk-ups or colossal 83-storey edifices. Mid-rise developments bring bustling activity to main streets but preserve the sunlight and sky views for the residential neighbourhoods behind them. Keesmaat’s plan for the city is to rezone the underdeveloped arterials like St. Clair, the Danforth, Eglinton, Lawrence and Kingston Road, and give automatic development approval to residential and commercial projects ranging from four to 11 storeys, which will take advantage of the underused parks, schools, sewers and water mains along those corridors. Mid-rise units are generally larger, cheaper per square foot and in massive demand among families and downsizers who need more space than a 700-square-foot condo. The scheme also co-ordinates land use with transit, creating jobs and homes along new TTC routes. (To sweeten the deal for developers, recent amendments to Ontario’s building code allow them to use wood frames for buildings up to six storeys, a cheaper option than concrete or steel.)

In 2013, Keesmaat launched Eglinton Connects, a pilot project for mid-rise development and land use co-ordination along the Eglinton Crosstown LRT route between Black Creek Drive and Kennedy, featuring $150-million worth of greenscaping and 20 kilometres of cycling lanes. “That’s the stuff that makes my heart pump,” Keesmaat says dreamily. The Eglinton plan was a huge success and recently won the award for planning excellence from the Canadian Institute of Planners. More studies are in the works across other arterials.

There has always been a simmering tension between planners, who preach livability, and developers, who are hungry for height and density. Keesmaat is big on densification—under her recommendations, council notably approved nearly 7,000 new condo units in one week back in August 2014, on top of the 70,000 already in the works. But no matter how much density Keesmaat allows, developers always want more. “They reach for the stars, and we have to compromise,” she says. “I was working on a project recently where the developers came forward with an incredible amount of density over multiple towers. We negotiated them down by half, and when I looked at the final product, it was still huge. I was like, have we been snowed?”

Most of the time, when builders want to pursue a development, they arrange what Keesmaat calls a pre-app meeting—an informal discussion about scope before an application is filed—where the planning team will tell the developers whether they need rezoning or an official plan amendment, if there isn’t enough green space at ground level, or if the proposed size is out of step with the surrounding neighbourhood. She says experienced developers know to schedule these meetings and usually bring ideas that are more or less in line with the policy framework. “We have many of the greatest developers in the world. Most of them want to build a better city,” she says, gushing over companies like Daniels (which was responsible for the Regent Park revitalization), Diamondcorp (Ordnance Triangle) and Rockport Group (which is redeveloping the historical Postal Station K near Yonge and Eglinton). “But like every other place, we also have some pretty crummy developers,” she adds.

She tells me about a recent meeting with one builder who had hired an architect from Dallas to design his project—a 1960s-style high-rise slab, the kind of brutalist eyesore you can see from space. He showed up at the planning department with no consideration for urban planning. When Keesmaat asked whether he’d read the guidelines, he admitted he hadn’t even looked at them. Other times, she says, developers will dangle candy, like a community centre or affordable housing, to distract the planning department from problems with the application.

Keesmaat’s biggest showdown came in fall 2012, when theatre producer David Mirvish announced he’d hired the architect Frank Gehry to create a trio of 80-plus-storey Jenga towers on King West, with six floors of commercial space in the podium and a gallery to house Mirvish’s collection of colour field art. The spires would stretch almost double the height of any neighbouring buildings and entail the demolition of the Princess of Wales theatre and four early-20th-century warehouses Mirvish owned. He skipped the pre-app meeting and hired a PR firm, announcing his project with the kind of grandeur you might find in one of his musicals. “They said, this is what we’re doing, like it or leave it. I think he’d agree now that didn’t work out so well,” Keesmaat says with a whiff of smugness. Her deal-breaker was the loss of the heritage buildings—she said she wouldn’t discuss the height, density or usage until that issue had been resolved. Her other big problem was the shadow his buildings would cast on Queen West, the heritage commercial conservation district (which she planned herself in her private sector days).

Keesmaat was staunch throughout the negotiations, eventually releasing a report to council urging that the height be reduced and the warehouses salvaged. Council sanctioned her recommendations and rejected Mirvish’s proposal. He was incensed. Keesmaat countered that such “bird poop architecture”—colossal, clumsy behemoths that developers plunk down in the middle of a streetscape—paid little attention to the surrounding urban fabric. By spring 2014, nearly two years after filing his original proposal, Mirvish returned to the planning department with a new design: two narrower, stacked towers, still shooting above 80 storeys, but no longer occupying the entire city block, freeing up sky views and sunlight for the Queen West heritage buildings behind it. The Princess of Wales Theatre and two of the four warehouses would be saved. “Frank Gehry sent me a thank you note after it was all over,” Keesmaat told me with the preening satisfaction of a kid who gets a gold star on her homework. “He told me how much better I’d made his project.”

I interviewed several developers for this story, most of whom spoke highly of Keesmaat’s charisma, initiatives and vision for the city, and about how game she was to work with them on high-density projects (they know who butters their bread these days). Some builders, however, said they thought the planning department was too stringent in their regulations. They complained about design restrictions imposed by the city’s tall building guidelines, and about the time it takes before a project can get approved by council. Peter Freed, the CEO of the downtown condo company Freed Developments, told me the department is programmed to say no. “You walk in and you’re greeted with no emotion, no response. It’s disheartening,” he says. “We should be incentivizing the people building the city to do exciting things.”

A few developers said they wished the planning department would take more leadership, that Keesmaat and her team would fight for more projects that lose out to political machinations at council. Keesmaat deftly navigates the push and pull. Sometimes, she says, completed developments don’t resemble their glowing futuristic renderings. Developers will stage a bait and switch, promising a dazzling new development from a prestige architect, then replacing him with a cheaper designer once they have approval from council. Keesmaat insists she can tell the difference, and suggests her team will only recommend the proposal when they’re convinced it will be executed properly. “There’s a myth in this city that it takes a long time to get a project off the ground. That’s only true for crappy proposals,” she says. “The developers whining about the process are the ones we don’t want to speed it up for.”

Some councillors, meanwhile, think she takes too much leadership. “She’s fighting so hard to be heard that she sometimes forgets that she also needs to listen. She sometimes misses the opportunity to see nuance,” says Adam Vaughan, who worked with Keesmaat on the Mirvish-Gehry file. A former councillor, who asked not to be named, told me Keesmaat needs to realize she’s a public servant, not a public master. Many, however, like how outspoken she is. “Why should we expect people who play leading roles in our city’s development to sit quietly behind the desk?” asks Josh Matlow, the councillor for Ward 22.

For Keesmaat, the problem with being a planner is that she’s not an executor. It’s impossible to know how her plans will pan out because of the plodding pace of bureaucracy. Keesmaat, fuelled by all that keyed-up zing, often gets impatient that red tape and politics are in her way. “It can be incredibly frustrating. We haven’t made as much progress as we could on the transit file, for example. There were decades where no building was done,” she says. But she won’t let herself dwell in those moments. She’s passionate about the power of democracy, bragging that her belief in the system overrides her impatience about its progress. One form of idealism trumps another. Keesmaat remains bafflingly, infectiously upbeat about the city’s current growth and future possibilities. “My favourite part of the job is watching buildings sprout from the ground,” she says with gusto. “I’ll often walk by a building site every day so I can see the change happening.”

Two figures loom large in the history of Toronto city planning. First came the doer: Roland Caldwell Harris, the city’s commissioner of public works who spearheaded huge growth between 1912 and 1945. In addition to hundreds of kilometres of sewers, sidewalks, roads and streetcar tracks, he created Toronto’s water purification system (which still provides 34 per cent of our clean water supply) and the Bloor Viaduct (which he insisted include a subway deck for trains that wouldn’t be built for another 20 years). Then came the thinker: Jane Jacobs, the prickly dissident who crystallized the way we now conceive of city building. She’s responsible for the tenets of urbanism and the idea of consensus between communities and policy-makers.

Jennifer Keesmaat will be remembered as the communicator—an articulate and compelling spin artist. She’s initiated conversational public roundtables on subjects like mid-rise development, suburban density and planning cities for families, bringing together experts from the building sector, the planning department and city council. She’s packaged all her public initiatives in digestible brochures, stripping away the bureaucratese and explaining how she and her team are working to fix the transit problem, or solve infrastructure deficiencies, or build organic neighbourhoods. Under her leadership, for the first time, the planning department is releasing annual reports—punchily designed packages in Magic Marker hues—that itemize their accomplishments; in 2014, they facilitated 160 project approvals, 14 civic improvement projects and a 250,000-tonne reduction in carbon emissions. Twitter, she suggests, is a platform for transparency as much as publicity. “There’s a risk to Toronto when people don’t know what city planning is seeking to achieve,” she says. “When I tweet something out, Torontonians can hold me accountable. They do all the time. And I looooooove that.”

It’s that kind of visibility that’s transformed her into a celebrity bureaucrat, oxymoronic as that may sound. She brags that she’s stopped on the street by fans every time she steps out the door. One day, as she was riding her bike down King West, a guy yelled, “Hey, chief planner!” When she turned around, he said, “Oh my god, it is you,” as if he’d seen Brangelina outside Roy Thomson Hall. Another time, she and Freeman were entering the subway at St. Andrew station when a besuited Bay Streeter held the door for them. “You better get going,” he said. “You have a city to plan.” Most of the time, people just say thank you, Keesmaat tells me with stately benevolence.

Behind the boosterism, there’s something genuinely aspirational about Jennifer Keesmaat, which feels almost rebellious in a city where the last mayor was all about saving gravy, the new one is all about making compromises, and council is splintered and inert. Her plan for the city is ambitious, expensive and radically far from fruition. But in that chipper Mary Poppins way of hers, she makes you believe that anything can happen if you want it badly enough.