The last two times a Winnipeg mayor fought to remain in office, fear was a component of the campaign.

In 2010, incumbent Sam Katz bought radio time to warn Winnipeggers they could "lose their homes" if Judy Wasylycia-Leis was elected and started raising property taxes.

Katz proceeded to raise frontage levies the following year and raised property taxes in 2012.

This year, Brian Bowman, running for re-election, is warning Winnipeggers of a different danger if they elect his primary challenger, business consultant Jenny Motkaluk.

At his campaign launch in September, Bowman warned Winnipeggers not to support competitors "who want to turn back the clock" to a time when unions and developers exerted influence over the mayor's office.

"We saw at her launch many of the old figures that used to call the shots at city hall," Bowman said several weeks later. Bowman has also referred to Motkaluk repeatedly as the "police union's candidate" in an effort to portray her as sitting in the back pocket of the Winnipeg Police Association.

Winnipeg Police Association president Maurice Sabourin shakes hands with mayoral candidate Jenny Motkaluk at a campaign event on June 26. The mayoral candidate is vulnerable to efforts to portray her as being cozy with the police union. (CBC)

On the surface, this sort of rhetoric may seem at odds with Bowman's sunny persona. After a campaign-launch speech where he proudly proclaimed "together we've set a new tone at city hall," Bowman suggested a vote for Motkaluk would return Winnipeg to an era of "old-school partisan politics of division and negativity."

The messaging here is clear: Bowman has attempted to portray Motkaluk as the second coming of Katz, a mayor whose 10 years in office will forever be remembered for the fire-paramedic station scandal, a series of real-estate scandals and the Winnipeg police headquarters debacle, which was the subject of two audits and an RCMP investigation that remains ongoing.

A missile finds a target

Motkaluk has proven vulnerable to these attacks, partly because of happenstance and partly because of her own actions.

The challenger cannot be blamed for the fact one of her brothers is a Winnipeg firefighter, an association opponents could use to claim she would not take a hard line on collective bargaining agreements with the United Fire Fighters of Winnipeg.

She also cannot be criticized for the fact another brother is a co-founder of Bayview Construction, a successful Winnipeg firm that was awarded $19 million of Winnipeg road-repair contracts in 2018.

Throughout this campaign, Motkaluk has never been shy to disclose what her seven siblings do for a living.

Motkaluk is, however, vulnerable to efforts to portray her as being cozy with the Winnipeg Police Association. For starters, police union leaders were present at two of her campaign announcements and helped her develop policy.

The first attack ad of the 2018 mayoral race claims Winnipeg has a shortage of 911 operators and suggests Mayor Brian Bowman is to blame. 2:03

More significantly, she offered support for a WPA social-media advertisement that exaggerated 911 response times and suggested children will be attacked by home invaders because of the Bowman administration's funding for emergency services.

"We did have a violent summer and it's clear public safety has been top of mind for a lot of people," she said after the ad was made public in September.

Following the money, today

Even more significantly, Motkaluk has refused to divulge the identity of her donors after Bowman made a short list of his campaign supporters public.

While the identities of all donors to contribute more than $250 to mayoral or council campaigns are eventually made public, doing so early is a good-faith gesture following the Katz era.

Motkaluk claimed such a move would violate her donors' privacy. It was an unusual decision that played straight into Bowman's attempts to suggest she is beholden to shadowy forces.

It also was unnecessary, as developers and real-estate industry figures have not been shy to support her mayoral campaign. Qualico's Eric Vogan, Terracon's Justin Swandel and former mayoral candidate Peter Kaufmann all attended her September campaign rally.

This is entirely logical. The development community, which justifiably complained city hall held no meaningful consultations prior to the imposition of growth fees, would not be acting in its own interest if it supported Bowman's re-election campaign.

Influence away from the mayor's race

While Bowman focused most of his attention on Motkaluk, an even broader effort to exert influence over city hall is underway.

The Winnipeg Labour Council, which has been active in every municipal election for decades, has endorsed seven council candidates. So has the United Fire Fighters of Winnipeg, which has also been very active.

The Winnipeg Police Association has not endorsed any council candidates, but has taken part in town halls about crime organized by Fort Rouge-East Fort Garry candidate Stephanie Meilleur, Charleswood-Tuxedo candidate Kevin Klein and River Heights-Fort Garry candidate Garth Steek, who is trying to win back the seat he held from 1995 to 2004.

The River Heights-Fort Garry proxy battle

Steek, who is trying to unseat nine-year incumbent John Orlikow, left city hall with his reputation in tatters, partly because of his role in the events examined by a City of Winnipeg audit in 2000, which concluded a Steek-led council property committee meddled in city real-estate deals.

After making an unsuccessful run for mayor in 2004, Steek was forced to repay the city thousands of dollars for credit-card expenses he initially claimed were incurred on city business during his final weeks as a councillor and became the first municipal election candidate ever convicted in Winnipeg for failing to file audited campaign expenses.

Steek continues to assert he did nothing wrong as property chair but has accepted responsibility for his credit card spending and campaign-expense filing.

Garth Steek is trying to return to the council seat he held from 1995 until 2004. He says he's learned from mistakes committed during his first stint on council. (Walther Bernal/CBC)

Steek also said he has learned from his mistakes. His record is relevant when you consider an ongoing real-estate saga in River Heights-Fort Garry: the development of the Parker lands.

Developer Andrew Marquess, who successfully convinced a judge to force the city to hold a Nov. 13 public hearing into a plan to develop the Fort Garry neighbourhood, stated in September he is supporting Steek in his fight to unseat Orlikow, the current chair of council's property committee.

A Steek victory over Orlikow would place the former president of the Manitoba Home Builders Association on the city centre community committee that will consider the Parker proposal. That does not mean Steek will vote in favour of a Parker plan on Nov. 13; he could just as easily do the opposite.

But Marquess has stated, explicitly, he hopes a new councillor in River Heights-Fort Garry will be more receptive to his plans than Orlikow, a councillor he has accused of stonewalling his development.

Following the money, eventually

Factor in every other developer upset with growth fees and all the council members who voted in favour of those fees, and you can see why Bowman and his allies would be afraid of their power, influence and campaign donations to competitors.

While the incumbent mayor released some of his donor names, he did not say how much they donated. It's unclear whether he is having any trouble fundraising, though an event was held as recently as last weekend.

"Fundraising is going very well," said Bowman campaign manager Kelly McCrae, who nonetheless declined to say how much money the campaign has raised.

All Winnipeggers will eventually learn that figure for Bowman and Motkaluk, along with the identities of the donors. But that won't happen until 2019, when the mayoral race will be a memory.​