I have an Olivia for Mayor sign in the yard.

Pretty much by reflex.

Yet, I’ve wavered.

Four days before casting a ballot, and I’m still unsure why she’s running for mayor this time around. Yes, yes. For a ‘caring’ city. For better transit. For more affordable housing. For a change from austerity and a baker’s dozen years of conservative rule, the clock down to zero on Tory time.

I get it.

But why Olivia?

Is she just a placeholder for the local NDP rump of politicians whose first couple preferences declined to run for mayor this time around? A faction that self-regards itself as the progressive option simply by its very existence. Everyone else outside the tent suspect, motivations dubious.

Does she fully comprehend the almost existential threat this city faces, not just from a budgetary perspective, although there is that, but for as long as Doug Ford remains premier of this province and his willingness to actively participate in the running of Toronto, our shadow mayor? That her old school negotiating skills, reaching out across the aisle to work with even those holding divergent views, may not necessarily be a strong point these days with opponents who really have no skin in a game that functions on compromise. That there are bad faith political players at City Hall and in Queen’s Park who will happily help the city burn a little more if it manages to undermine Chow’s performance in the mayor’s office.

She has, to my mind, largely been successful contending with those types of baying attacks from the more immoderate contenders on the campaign trail, not withering under the fuselage of bullshit they’ve flung at her. Such anti-Chow zealotry, which is significant – those disliking her and her candidacy dislike her a lot – has failed to coalesce behind any one of her rivals. A sign, perhaps, more of the respective glaring weaknesses of those campaigns rather than the strength of hers. But, then again, maybe I’m not giving credit where credit’s due.

If Olivia Chow is elected mayor of Toronto on Monday, navigating such treacherous waters while attempting to govern will be a whole lot more difficult. Egged on by what will surely be a truculent provincial government (“You want my opinion?” the premier opined yesterday. “If Olivia Chow gets in, it will be an unmitigated disaster,”), she will, quite possibly, face a hostile city council in the majority that committee chair appointments and proximity to power will not fully placate. Her mayoralty may be challenged as ‘accidental’, nothing more than interim until the next real election in 2026.

Which would be, you know, fine. Entirely theoretical at this point, and while the thought of many of those useless Tory remnants relegated to the figurative backbenches for their negligence committed against the city during their time in office is edifying, I’m not convinced Chow has positioned herself with the inspiring cudgel necessary to bludgeon enough of them into compliance. Because, this is what it feels like right now. War-footing rather than cooperation and conciliation.

That too melodramatic?

For a municipal mayoral by-election?

Probably.

Perhaps, it’d be less incendiary to say that I know what Chow is fighting against. I’m just unsure exactly what she’s fighting for. Yeah, yeah. Fairness. Justice. A more ‘caring’ city. Survey the other 101 candidates in the race and you’ll get 101 variations of the same theme. That I actually believe Olivia Chow, stands mightily in her favour. What I’m missing is the unabashedly, unapologetic left wing, ‘progressive’ noisemaking that seems called for these days. Some finger-poking to the eyes of her critics, a full-frontal assault on what is an utterly inadequate status quo. Forget modest. I want to hear Whatever It Takes.

I want a little more Josh Matlow.

I know, right?

Who could ever imagine such a thought wafting up from these pages? As I tried working through his political journey, the councillor has beaten a path from the wilds of the mushy middle during the Ford years to being, arguably, the most outspoken critic of the John Tory administration at City Hall. An always oppositional figure with few natural allies on council (or, I imagine, city staff, not irregular targets of his public criticism), Matlow may be best positioned to directly confront the forces of antagonism toward Toronto including the premier and a bunch of Tory allies on council determined to keep up the snail’s pace of nothingness that was the former mayor’s specialty. It will be an uphill battle for the next mayor, to be sure, but that’s sort of been Matlow’s specialty, relentless windmill tilting.

During this campaign, he was out of the gate quickly, policy announcement after policy announcement, putting together a ‘fully costed’ platform (the pride and joy of his very enthusiastic supporters), proof positive of his serious intentions to realistically and progressively deal with the daunting problems the city faces. Only Chloe Brown and, latterly, Mitzie Hunter would match Matlow in terms of attention to detail. A luxury frontrunners can afford not to fully engage in. A Why not them? versus a Why them? dynamic.

But Josh Matlow has ably answered Why him.

He seems to be prepared to try and take the city in the direction which I believe it needs to go. He seems prepared to stand up with the limited powers he has to defend that direction. Even though he’s been a city councillor for over 13 years now, his career has been one of being on the outside so that it almost feels like he’d be bringing fresh blood and ideas to the mayor’s office.

The one thing that niggled, bringing me short of a full-blown embrace of Matlow for mayor, is the idea of yet another straight, white male, a midtown straight, white male, no less, elected mayor of Toronto, yet again, touting his progressive cred. How does that reflect this city? Two steps forward and one step in place if not backward.

Josh Matlow’s worked diligently to show his progressive bona fides. Olivia Chow’s been living them for nearly 40 years in public life. There’s little question where her priorities will be from day one in the mayor’s office. With Councillor Matlow, you will need to make a leap of faith, trusting that his latest political transformation sticks.

This contrast became apparent to me a week or so ago when footage surfaced (with the help of opposition research, no doubt) of Matlow engaged in a post-debate scrum exchange with a ghoul from Rebel Media, a hate-filled troll factory with a website, that all the other candidates present seemed to have rightly avoided or kept contact down to the barest minimum. What the fuck was Josh doing, platforming this hideous organization? He couldn’t have been unaware who they were or why they were present.

Then, I remembered something Navneet Alang uncovered in his excellent article on Matlow in The Local. “There is no one perspective that is completely more virtuous than the other,” the then-rookie councillor pronounced on his radio show back in 2011. As a matter of fact, Josh, yes, yes there are some perspectives more virtuous than others. There are some perspectives that are utterly drained of any aspect of virtue whatsoever. Perspectives consistently espoused by Rebel Media.

And yet, there’s Josh Matlow earnestly engaged in a spirited back-and-forth with a professional, cap-wearing troll. To what end? He couldn’t possibly think he would be swaying many votes his way from their followers, could he? Matlow didn’t believe he was engaged with objective, honest brokers, did he? If so, wow.

Inevitably, he delivered up what the outlet was angling for with a mild criticism he lobbed at Chow. In the edited version for the website, Matlow’s jab is followed by a photo of Chow surrounded by a group of pink-clad Pride event attendees(??). Bingo! Every scary box checked off for Rebel Media viewers, facilitated by Chow’s main progressive rival.

It cost Josh Matlow little to provide the fodder. He wasn’t really the target in the first place. He was just there to help. Thirteen years at City Hall and he still doesn’t get it. He doesn’t get being marginalized, being othered. Being a true outsider and spending his entire political career prioritizing the needs and values of all those who truly are. Josh Matlow doesn’t get it, not fully, because he doesn’t have to. That’s the difference between Josh Matlow and Olivia Chow. She’s had to get it. She’s had to live it.

That’s why, in the end, I’ll be voting for Olivia Chow for mayor on Monday.