'A mad dash' to fill an open field begins, as Brian Bowman announces he won't run again

Winnipeg Mayor Brian Bowman unleashed two waves of local political speculation late last week, when he announced that he would not run for re-election to a third term in 2022.

Announcements like these are not uncommon in mayoral politics in Canada or the United States. But the timing is very unusual.

Most mayors would wait until at least the end of their third year of a term to bow out, just to avoid turning themselves into a "lame duck" too early.

Bowman's announcement comes a full year earlier than that, which makes his job both much easier and much harder in a single instant.

The first wave of speculation will likely fade eventually, since time will tell whether the mayor timed this announcement with some unknown other purpose in mind. But the second wave of speculation is likely to grow in volume.

When a big-city mayor stands up and basically invites people to run for his job, a lot of people are going to ask themselves if they should accept the invitation. Running against incumbent mayors is often an easier grind in Canada, even though incumbents are tough to beat, because the head-to-head contest makes it easier to stand out and run against the incumbent's record.

But to the general political public, open races look easier and so the result is pure chaos as candidates begin a mad dash to fill the open field.

I made a few inquiries with local political hacks on the weekend, and if you add together the list of "plausible" candidates, "certain" candidates and "someone is planning for them whether they know it or not" candidates, the list is already exhausting.

Who might run?

In no particular order, city councillors Jeff Browaty(North Kildonan), Sherri Rollins(Fort Rouge-East Fort Garry), Brian Mayes(St. Vital), Ross Eadie(Mynarski), Scott Gillingham (St. James)and Markus Chambers (St. Norbert-Seine River) all come up as ticking one, two or even three of those boxes. One more name on council comes up often, but we will get to him later.

Put together, roughly half of city council was likely either taking calls from potential supporters, or making them, soon after Bowman's announcement.

Outside city hall, names like provincial Municipal Relations Minister Rochelle Squires and Northern Affairs Minister (and former acting mayor) Dan Vandal come up in the "plausible" column, not least because the mayoralty has become a popular final career stop for cabinet ministers in Ontario and British Columbia.

Names like Dayna Spiring (currently running Economic Development Winnipeg) and former MLA Colleen Mayer also come up with a few pundits.

The world of local professionals, business leaders and urbanist activists is fertile ground for candidates, too; three of the last four Winnipeg mayors did not hold elected office before they won, and two had never run at all. (Most local observers forget that Sam Katz took an early run at city council, losing to a local activist named Glen Murray).

The problem with an open mayoral race: it's like buying a lottery ticket. But the advantage is: it's like buying a lottery ticket.- Brian Kelcey

And if I haven't mentioned your name above, don't worry there's plenty of time to drop it in.

The sheer number of potential candidates who might at least stop to consider a future run in an open race is, in a word, crazy. Bowman's early announcement only pours gas on that fire.

But here's the thing: even the long-shot hopefuls aren't necessarily wrong to hope.

A ticket in the lottery

The problem with an open mayoral race: it's like buying a lottery ticket. But the advantage is: it's like buying a lottery ticket.

Mayoral races are notoriously long and unpredictable, and these attributes create room for a whole class of what I call "back of the pack" candidates, with financial and organizational stamina, a loyal network, a good personal story and (most importantly) a distinct and positive message.

Back of the pack winners often secure big wins, even though they start in third, fourth or even fifth place with as little as three to 12 per cent support at the outset. Examples of the genre include Toronto's David Miller (2003-2010), Calgary's Naheed Nenshi (2010-present) and, notably, Brian Bowman himself.

Two of America's largest cities New York and Chicago are led by back-of-the-pack winners, namely Bill de Blasio and Lori Lightfoot, respectively. Even London's Sadiq Khan was a long-shot backbench MP polling well behind his peers when he first ran for Labour's mayoral nomination.

In other words, the next mayor of Winnipeg in 2022 might very well be someone who you've never even heard of at this moment in 2020.

My free advice to any one of the 500,000 Winnipeggers thinking about running after reading this is: if you're serious, don't start by building your campaign. Don't politick. Don't send out press releases or create a new social media account to build your profile.

The reason not to do these things is Coun. Kevin Klein (Charleswood-Tuxedo-Westwood), the person in local politics who looks and sounds the most like a person who craves the mayoralty right now, even if he is likely to be coy about it.

For many months, he has been Mayor Bowman's leading critic. And if you take the comments and the motions and the blog posts one at a time, many of the councillor's criticisms are valid. But put it all together, and there is an unspoken undertone beneath it all, whispering that "being mayor would be so much easier if only the mayor was me."

A word of warning to all 500,000 of you: there's a consistent lesson I've seen and heard from hundreds of conversations and sources on the mayoralty as an institution. Every single mayor who's expressed an opinion on the matter was surprised or even shocked at the scope, the scale and the complexity of the job once they got it.

Veteran city councillors think they know better, as if the job is "city councillor plus," but it transcends that. Hell, even Mayor A.C. Wharton was mayor, twice. He was mayor of a Tennessee county before he became mayor of Memphis, and he insisted his county mayoralty didn't really prepare him for the scale of big city mayoring.

How to become Winnipeg's next mayor

So that's why my advice to any mayoral hopefuls is to take the time that Bowman has so kindly given you, and don't position. Don't posture. Don't preen. Don't take shots.

Instead: do something. Make something. Build something. Pick a cause, a project, an enterprise, whatever it might be, that will make Winnipeg a better place, and just go out and do it. Make it happen. Lead.

Save something that needs saving in the COVID-19 economy. Fix a mess that needs fixing. Find funding for something that deserves it.

If finishing one positive project to set oneself apart seems too daunting for a prospective candidate, it might be better to consider buying into a different lottery entirely.- Brian Kelcey

For those on city council or in the legislature, build a coalition to achieve something that wouldn't happen otherwise, with councillors or MLAs or stakeholders who you might not otherwise talk to.

There are two reasons for potential candidates to consider action over words as the next step in their political campaign for the mayoralty. The first reason is that action and achievement will make one's story as a candidate far more compelling and credible than a tidy resume.

Since mayors have little formal power, even in Winnipeg's system, the best mayors in the world conjure up action, momentum and results from nothing, like political sorcerers. If someone can build something outside city hall, they might just be able to do it inside.

But the most important reason is self-assessment.

Look at it this way: if a candidate can't make one new, significant, worthwhile interesting thing happen in this city before they actually aspire to run it, imagine how much like hell the actual job will feel, as they face expectations to solve 50 problems at once, with a thousand professional critics shouting them down every step of the way.

And if finishing one positive project to set oneself apart seems too daunting for a prospective candidate,it might be better to consider buying into a different lottery entirely.

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