Winnipeg’s wide-open mayoral race is shaping up to be the most competitive in decades — and not just because seven candidates have already registered their campaigns.
Five of those candidates vying to become the city’s 44th mayor either have experienced campaign managers on their team or a large volunteer base.
This means there will be no easy path to the mayor’s office for anyone in October, even without an incumbent in the race.
There’s also no shortage of familiarity among some of the people working for these candidates instrumental roles, as several have worked alongside or competed against each other. There are only so many people available to manage mayoral campaigns.
For starters, St. James Coun. Scott Gillingham — who briefly flirted last summer with the idea of running for the leadership of Manitoba’s Progressive Conservative Party — has two veteran Winnipeg political organizers on his team.
Luc Lewandoski, once Gillingham’s city hall executive assistant and a former handler for a number of PC cabinet ministers, is managing the councillor’s mayoral campaign. Brian Kelcey, a former Sam Katz policy advisor who turned into one of the former mayor’s most vociferous critics, is putting together Gillingham’s platform.
Kelcey provided some policy advice to Jenny Motkaluk when the business consultant ran in the 2018 mayoral race. In her second run, Motkaluk is promising less of a focus on policy, but she has a recently victorious campaign manager in her corner: Fred Westphal, who managed Progressive Conservative candidate Obby Khan’s successful bid for the provincial Fort Whyte seat.
Westphal is effectively in a campaign rematch against his Fort Whyte opponent. Nikos Kioussis managed Liberal candidate Willard Reaves’s near-upset in Fort Whyte, and is now managing the mayoral campaign for Wilderness Supply owner Rick Shone.
Kioussis is also the Manitoba Liberal Party’s director of organizations, and finds himself competing in this mayoral race against another Liberal.
Eric Stewart, a former provincial party advisor, is managing former Liberal MP Robert-Falcon Ouellette’s second run for mayor. Stewart has managed Ouellette before at the federal campaign level.
The fifth mayoral candidate with a visibly organized campaign is former provincial environmental policy director Shaun Loney, who showed up to register at city hall with a crew of 28 supporters, including several well-connected community organizers.
Mayoral candidates need volunteers and experienced campaign staff if they’re serious about winning. Popular support only goes so far for candidates who don’t have volunteers who can identify the people most likely to vote for them — and the means to ensure those people show up to vote.
During Winnipeg’s last wide-open mayoral race in 2014, there were at best four organized campaigns. Only Brian Bowman, the winning candidate, and runner-up Judy Wasylycia-Leis were backed by what appeared to be sophisticated electoral machines.
More potential candidates
There could be eight or more organized campaigns this year, as Manitoba Families Minister Rochelle Squires, former provincial Liberal leader Rana Bokhari and former Winnipeg mayor and Ontario Liberal MPP Glen Murray have all been the subject of polls to gauge voter support.
Murray did not respond to requests for comment. Bokhari would not confirm or deny an interest in running for mayor, and said she will declare her intentions soon.
Squires declined to confirm or deny an interest in running and suggested she will state her intentions after June 1. According to city rules, she would not have to resign her seat in the Manitoba Legislature if she chooses to run for mayor.
Even without more candidates, the potential field of organized or well-known candidates would dwarf the Winnipeg mayoral races of 2014, 2004, 1998 and 1992 — when, respectively, Bowman, Sam Katz, Murray and Susan Thompson were first elected.
With so many strong candidates running this year, fractured voting will make campaign organization matter even more. With a crowded field, Winnipeg may not elect the most popular mayor, but the one who did the best job of identifying their supporters and getting them to the polls.
Popular opinion matters more in races with fewer candidates, where small differences in voter support tend to get magnified beyond the ability of organized campaigns to overcome.
This is why politicians who enjoy strong name recognition — such as Charleswood-Tuxedo-Westwood Coun. Kevin Klein, who mused for months about running for mayor — may choose to sit out the 2022 race.
While it will take a tremendous amount of work for any mayoral campaign to succeed this year, there is no guarantee that hard work will translate into a victory.
Most of the candidates registered this year have at least one strength.
Ouellette and Motkaluk have mounted organized mayoral campaigns before. Gillingham has a considerable amount of council experience. Shone, the co-creator of the Swamp Donkey adventure race, could tap into a built-in network of highly motivated endurance racers. Loney can rely on a large network of community activists.
In other words, anyone who tells you today what will happen on election day in October is talking nonsense. At this very early juncture, anything can happen.