If nothing else, Jennifer Keesmaat will go down as one of the city's most passionate popularizers of planning. Appointed Toronto's first female chief planner in 2012, she quickly revealed a talent for making people pay attention to issues that normally left them yawning.

This week, after five years on the job, Keesmaat unexpectedly announced she would step down at the end of September “to pursue other interests.” But given her local celebrity, many believe the move is a prelude to greater things — a political career, perhaps, or even a run at the mayoralty.

Keesmaat assumed her position during the dark days of Rob Ford. His reputation was such that many observers believed no big-name candidate would take a job that meant working under Ford. In fact, the chief planner reports to the city manager, not the mayor. Keesmaat, then relatively unknown, got the gig and quickly became the most high-profile chief planner in Toronto's history. But as she soon found out, the chief planner's role is to advise not to decide. That could mean being overruled, or worse, ignored.

That put her at odds with the city's political masters, most notably Mayor John Tory, whose outdated notions of city-building run counter to the received wisdom of contemporary planning. Keesmaat's progressive ideas were light-years ahead of Tory, most members of city council and large segments of the civic bureaucracy. Though she was a vocal advocate for an enhanced public realm, more bike lanes, improved pedestrianism, better transit, and reduced dependence on cars, her political masters preferred things the way they are. And when they agreed, it was reluctantly.

Most notably, she clashed with Tory over his antediluvian plan to rebuild the east end of the Gardiner Expressway. City staff recommended taking down this decrepit stretch of the elevated highway, but municipal politicians and local media decided against that because it would increase commute times from the east by minutes. She lost that fight, and the city is on track to spend $1.5 billion in its vain quest for traffic nirvana.

At the same time, Keesmaat squandered considerable professional capital putting a gloss of respectability on discredited schemes such as the one-stop Scarborough subway extension, which any planning undergrad would rightly have dismissed out of hand as an obvious waste of money and resources.

On the other hand, her support for the King St. pilot project will go a long way to help drag Toronto into the modern age. The plan is designed to prioritize transit — specifically streetcars — by giving them the right of way. Though almost 200 parking spots will be removed and cars forced to turn right at many intersections between Jarvis and Bathurst, council voted overwhelmingly in favour of the proposal.

Speaking of King St., Keesmaat's response to the Frank Gehry/David Mirvish multi-use complex just east of John St. marked a low point in her tenure. Speaking to the Star in 2013, she called Gehry's design “trite” and wondered whether Mirvish could be trusted not to pull “a bait and switch.” After much to-ing and fro-ing with the city, Mirvish reduced his proposal from three towers to two and watered it down to fit with Toronto's traditional timidity. Gehry's design will be a landmark, though not as spectacular as originally conceived. Keesmaat's failure of imagination was especially galling in a city that approves generic glass-and-steel towers by the dozen.

Through it all, however, Keesmaat was able to communicate the precepts of progressive 21st-century urbanism with the ease of a TV game show host. Telegenic and articulate, she forged a bond with Torontonians unlike anything achieved by her predecessors or, indeed, most politicians. She spoke the same language as millennials and came across as fresh, enthusiastic and engaged in a municipal culture that can feel beaten down and mausoleum-like. Where everyone around her — including her own department — seemed preoccupied by the city's most banal issues — dog turds, parking and shadow studies — she offered a sunny vision of a Toronto that was comfortable yet exciting, where kids could be happy and their parents confident.

Ultimately, though, the decisions weren't hers to make. The grinding realities of politics and planning in Toronto leave little room for more than applying the rules and ticking off the boxes. Certainly Keesmaat showed she can talk the talk, perhaps now she hopes to walk the walk.

Christopher Hume’s column appears weekly. He can be reached at jcwhume4@gmail.com