The Mayor’s gamble

South Osborne

Hey there, time traveller!
This article was published 16/07/2025 (309 days ago), so information in it may no longer be current.

It’s been over a week since Winnipeg Transit’s major overhaul came into effect, and reactions have predictably been mixed — and predictably negative — as riders scramble to adapt to new routes and new routines.

But the legitimate concerns and wide range of views coming from the diversity of people that regularly take the bus have already been covered elsewhere.

So what can a community correspondent for South Osborne add in a short column?

I used this space some time back to describe a political theory that explains why leaders behave the way they do. In short, no leader, in any system or of any stripe, can lead alone. Assuming they want to keep their job, they need to reward the people whose support is essential to keeping them in charge.

In democracies they rely on a lot of people, so the best way to dish out rewards is through public goods. But those are expensive and money is limited, which explains the tendency to over promise and under deliver.

It also explains the tendency to borrow: because any wise leader knows that a society’s financial crisis sooner or later becomes their own political one.

Under the city charter, Mayor Scott Gillingham can’t borrow, so his position is unique. He has acknowledged that the city is underfunded, and openly expressed his opinion that the city and province need to come up with a new model to fund city services.

It was an easy sell to the general public, according to a poll City Hall itself commissioned last winter. By a 2-1 margin, respondents unsurprisingly preferred more funding from other levels of government to the alternative of levying new taxes, or raising existing ones.

But the mayor convinced council to approve hikes to trash fees and sewer rates this past spring to cover basic services.

He also has ambitious promises to keep, and hasn’t shied away from shuffling his inner circle on the Executive Policy Committee to push his agenda. In January, Fort Rouge-East Fort Garry councillor Sherri Rollins also stepped down from it, citing “an accumulation of concerns.”

Given his unique situation, and willingness to implement unpopular ideas, the question becomes who is he producing results for?

There is arguably no community in Winnipeg with a fate more closely tied to transit than South Osborne. Transit’s head office and one of its main garages are located in the neighbourhood, along with the first rapid transit corridor. There is also a proposed housing project, one of two in the city, tied to transit hubs.

It is also the heart of Premier Wab Kinew’s own constituency.

Of course, an improved transit system is to the wider benefit of the entire city, and so will be his other promises on housing, homelessness, and crime, should he be able to keep them. But for that he’ll need more than basic operating costs, and to work well with other levels of government.

Mayor Gillingham has shown himself willing to take risks. Let’s hope this one pays off.