Klein put on defensive as mayoral run made official
Gillingham, union, cabinet minister take shots on candidate’s record, character
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Kevin Klein faced a barrage of attacks from the city’s incumbent mayor and largest union as he officially entered Winnipeg’s mayoral race Thursday.
While the former city councillor and Progressive Conservative cabinet minister was registering to run at city hall, Mayor Scott Gillingham’s team sent out a news release noting Klein was one of two councillors to vote against pursuing legal action against participants in the Winnipeg police headquarters scandal.
Shortly after, Canadian Union of Public Employees Local 500 accused Klein of blaming Canada for its ongoing trade war with the U.S. and called him an “unfit” candidate who would “bend a knee to American interests” in a news release of its own.
MIKAELA MACKENZIE / FREE PRESS Kevin Klein registers for the mayoral race at City Hall on Thursday, Sept. 3, 2026. For Malak story. Free Press 2026
Klein defended himself outside city hall after putting in his papers.
“A lot of people are saying a lot of things about me, and it would seem to me it’s probably because Scott Gillingham seems a little afraid to stand up to his record,” Klein, 61, told reporters Thursday morning.
He said he’s considering legal action against Gillingham and accused him of peddling “conspiracy theories.” Within hours of Klein announcing Tuesday he was throwing his hat into the mayoral ring, a news release from the mayor described Klein as a “fixer” for convicted sex offender Peter Nygard and a supporter of U.S. president Donald Trump.
Klein called the mayor’s words “childish” and “disappointing,” and said those comments are “in the process of being reviewed by legal counsel.”
“He started a smear campaign based on lies, he threw in a few conspiracy theories, and clearly, this is not the type of election I’m going to have,” he said.
Gillingham didn’t mince words later in the day when discussing potential legal action from Klein
“I look forward to the discovery,” Gillingham, 58, said, referring to the process of opposing sides in a lawsuit exchanging evidence.
In 2020, Klein, then the councillor for Charleswood-Tuxedo-Westwood, voted against approving the use of funds to seek legal counsel over the Winnipeg Police Service HQ scandal, after an audit determined the project was severely mismanaged and cost taxpayers tens of millions more than originally anticipated. Klein and former Transcona councillor Shawn Nason were the only two to vote against using funds for legal action.
The subsequent lawsuit ultimately resulted in a $28-million settlement for fraud and construction deficiency in favour of the city.
“When you’re the mayor, you’ve got to have the courage to make decisions for the people of Winnipeg, even if it’s a case like that where there’s legal matters involved,” Gillingham said. “We made the right decision, $30 million has been recovered now for the people of Winnipeg.”
Klein said he voted against taking legal action at the time because he wanted more information on the cost to the City of Winnipeg.
“I’m glad that I was wrong and they got their money back,” he said. “I’m happy about that, but I stand by the fact that I had to do something because nobody was giving the people information.”
Meanwhile, CUPE Local 500 pointed to a Winnipeg Sun column written last month by Klein, with the headline Strong leadership isn’t trading jabs for applause as an example of his “softer trade posture toward the U.S.”
Klein, who is the president and CEO of the company that owns the Sun, was critical of insulting comments made by Premier Wab Kinew about Trump.
“There is no place for Canadian leaders to fall offside with Team Canada … this really shows that Kevin Klein is an extremist and outside the mainstream of Canadian politics,” said Gina McKay, president of CUPE Manitoba, in a news release.
Klein called CUPE’s comments “a 100 per cent lie.”
“I’m very Canadian, I’m proud to be Canadian, I carry the Canadian flag very proudly,” he said.
In July, Klein attended and wrote about a gathering in Ottawa that was hosted by U.S. Ambassador Pete Hoekstra.
He said he stands by that visit as an opportunity to promote Winnipeg.
Klein’s decision to run for mayor a second time — he finished third in the 2022 mayoral race with 28,806 votes — also invited criticism from a Manitoba cabinet minister.
MIKAELA MACKENZIE / FREE PRESS
Kevin Klein said he voted against taking legal action against participants in the police headquarters scandal because he wanted more information on the cost to the City of Winnipeg.
Families Minister Nahanni Fontaine posted a 55-second video to social media Tuesday, pointing to Klein’s time working for Nygard.
She titled the video “I mean really, who chooses to work for Count Dracula?” and included a vampire emoji.
“Kevin Klein once worked for Peter Nygard, Peter Nygard is Canada’s equivalent to (American sex offender) Jeffery Epstein — had his own little island, did unspeakable, disgusting things to women and girls … anyways, I just thought that Winnipeggers would want to know that Kevin Klein, at one point, worked for Peter Nygard,” she said in the video.
Klein worked for the fashion mogul for about four months in 2012 and again for two weeks in 2014. Nygard was later convicted of multiple counts of sexual assault and is in an Ontario prison.
He described Nygard as a “bad man” Thursday, but said thousands of people had worked for him over his career, and it would be unfair to judge any of his many employees by his actions.
“I was taught as a minister that you have to hold yourself to a higher account. You’re in a higher office, you’re representing the province of Manitoba, you’re representing the Crown,” Klein said. “And I was also told that you never get engaged in municipal politics.”
A provincial spokesperson for Fontaine and Premier Wab Kinew declined to comment.
A member of the provincial government providing commentary on a candidate in a mayoral race is “unusual,” said Christopher Adams, a University of Manitoba adjunct professor of political science.
“I was surprised that a cabinet minister would be commenting about a candidate in a civic election,” he said.
“I can’t remember this happening before, and I’m sure some of the members in the legislature are a bit uncomfortable with that.”
The political expert also called Gillingham’s coming-out-swinging approach “out of character” for the typically milder-mannered mayor.
“I think both of these candidates will be very aggressive, judging by what we’ve seen the past (48) hours,” he said.
Ten other candidates are running to become mayor. Michael Vogiatzakis, Christopher Clacio, Umar Hayat, Mazher Alam, Don Woodstock, Joshua Pagdato, Johnny Calderon, Noah Redden, Zac Uminski and Brad Gross have all previously registered.
Election Day is Oct. 28.
— with files from Joyanne Pursaga
malak.abas@freepress.mb.ca
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History
Updated on Thursday, September 3, 2026 5:39 PM CDT: Adds quotes, headline changed.