Jennifer Keesmaat may not know exactly what her next political move will be — but she knows what it won’t be

Despite losing the Toronto mayor’s race, the former chief planner secured 180,000 votes. Do they represent a base of support for future runs?
By Steve Paikin - Published on January 16, 2019
Jennifer Keesmaat emerged from the 2018 Toronto mayoral race carrying no debt and having learned how to campaign and fundraise. (Christopher Katsarov/CP)



It’s become a bit of a parlour game, at the end of every Toronto mayoral election, to speculate on what the runner-up will do next.


It happened four years ago, when Doug Ford, having picked up the torch from his dying brother Rob, had an unusually strong showing for someone who’d entered the race at the 11th hour. Three years later, Ford became leader of the Ontario Progressive Conservatives; three months after that, he became the province’s 26th premier.


Eight years ago, observers speculated about the future of former deputy premier George Smitherman, who’d just lost the mayoral election to Rob Ford. Smitherman tried to re-enter politics as a candidate for the federal Liberals in 2015 but was rebuffed. He also unsuccessfully sought a Toronto city council seat last October.


All eyes were on John Tory after his performance in the 2003 mayor’s race. Tory started that campaign at 3 per cent in the polls but wound up with 38 per cent of the vote — putting him just five points back of the winner, David Miller. A year later, Tory parlayed that into a successful run for the Ontario PC leadership (and, of course, he later won the mayoral elections of 2014 and 2018).


And ever since Tory secured his second term as mayor in October, politicos have been wondering what Jennifer Keesmaat’s next move will be.


You’ll remember that last year, just minutes before the deadline, the former chief planner unexpectedly signed up to challenge Tory despite having earlier pledged not to do so. She instantly became the champion of the city’s progressive elements, even though she’d never run for office before.


Keesmaat found herself up against a popular, well-financed incumbent who portrayed her as a last-second upstart, captive to NDP interests. Keesmaat, now 48, had never thought of herself as a New Democrat, but Tory was able to define her that way before she got the chance to put her own frame around her political agenda. If Keesmaat wanted to convince voters that she wasn’t a New Democrat, she probably didn’t help matters by appointing former federal NDP leadership hopeful Brian Topp to run her campaign. The fact is, there were Liberals on her campaign team as well, but the NDP seemed to embrace Keesmaat more overtly.


On election night, it wasn’t close. Tory took more than 63 per cent of the vote, finishing a remarkable 40 points ahead of his challenger.


Still, Keesmaat emerged from the contest carrying no debt and having learned how to campaign, fundraise, and do media interviews — not as a neutral and respected bureaucrat, but as an elbows-up political candidate, fighting to get her message out.


In the months since election night, many observers have wondered whether Keesmaat will take that new experience and knowledge and put it toward another campaign. She’s already been asked to consider seeking a nomination in a Toronto-area riding and run in the 2019 federal election. And, with former premier Kathleen Wynne expected at some point this year to resign from provincial politics, some have wondered whether Keesmaat might contest the inevitable byelection in Don Valley West, in the heart of midtown Toronto, and thereby put herself in the conversation for the Ontario Liberal leadership.


Right after the last municipal election, a friend of Keesmaat asked whether she’d ever run for anything again.


“Not a chance,” was her immediate reply.


Then the friend pulled out her smartphone, hit the record button, and asked the question a second time.


“Will you ever run for office again?” the friend asked, this time looking to keep a copy of the reply for posterity.


“Probably not,” Keesmaat sheepishly answered.


It then seemed to occur to her that, if the answer had become less categorical over the course of just four seconds, she might need to come to terms with the idea of potentially running again.


“I do know this,” Keesmaat told me earlier this week. “I won’t be running federally, and I won’t be running provincially.”


It seems her heart is still with municipal issues. That may be why she’s turned down almost all media interviews dealing with the policies of Doug Ford’s government: she doesn’t want to give the impression that she’s part of the provincial political opposition — even though she does, in fact, oppose the premier’s municipal agenda.

Keesmaat is now in the process of putting together the pieces for the next stage of her career; she tells me that she expects to make her intentions public in six weeks or so.


And she points out that despite losing the mayoral race, she secured nearly 180,000 votes last October — almost as many as the victorious mayor of Ottawa, twice as many as the victorious mayor of Mississauga, and four times as many as the victorious mayor of Brampton.


Could those votes represent the core support for a future run at the Toronto mayoralty? After all, success didn’t come to the current mayor until his second attempt. At any rate, I suspect we haven’t heard the last of 2018’s mayoral runner-up.

Thinking of your experience with, how likely are you to recommend to a friend or colleague?
Not at all Likely
Extremely Likely

Most recent in Politics