Stefanson pins re-election hopes on friends outside government

It is not unusual for governing political parties facing re-election to fight a series of internal battles long before they cross swords with other parties during the campaign.

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It is not unusual for governing political parties facing re-election to fight a series of internal battles long before they cross swords with other parties during the campaign.

It’s the nature of politics. When things are not going well, there is always a round of finger-pointing followed closely by desperate efforts to find a saviour. Sometimes these battles breathe new life into a government and get it back on track for re-election; sometimes they hand the reins to people who can do no better than finding a quicker route between the threat and the political abyss.

Just such a battle is unfolding in the ranks of Manitoba’s Progressive Conservative party.

Don Leitch, the clerk of the executive council, was fired two weeks ago. (Mikaela MacKenzie / Winnipeg Free Press files)

Nearly two weeks ago, in a surprise move to “refresh” her senior staff, Premier Heather Stefanson fired chief of staff Phil Houde and Don Leitch, the clerk of the executive council. The staff moves were surprising for people inside and outside the party.

Houde, who has worked for several Tory leaders, including former premier Brian Pallister, had just agreed to come back on board last June; Leitch came out of retirement in October 2021 and, essentially, served as a trusted adviser to Stefanson when she became leader, and thus premier, the following month.

Multiple party and government sources said when Houde arrived in June he was able to, working closely with Leitch, create some stability in the premier’s senior-most political staff, helping Stefanson avoid the strategic and communication gaffes she suffered in her initial few months as the first minister.

However, sources confirmed that Houde and Leitch were in constant conflict with two other key players in Stefanson’s political universe: strategists Marni Larkin and Michael Diamond.

Unbeknownst to outside observers, Larkin and Diamond have been appointed by Stefanson to chair the Tories’ 2023 election campaign. Their presence is a clear sign that whenever the election is called this year — it must be held no later than Oct. 3 — Stefanson is looking for someone to mount a more aggressive strategy.

More often than not, a campaign manager will come from a member of a party leader’s political staff in order to have some insight into government business that has the potential to become an election issue. In this instance, however, Stefanson chose two people outside executive council who were — in legal and administrative terms — not entitled to some government information.

Battles over this exchange of information, along with significant disagreements on overall strategy, led Larkin and Diamond to issue an ultimatum. By all accounts, Stefanson has decided to hitch her wagon to Diamond and Larkin, who are longtime family friends, and say goodbye to the veterans in her office.

“Phil and Don served the premier well but in the end, she simply did not believe they were the people to get her over the finish line,” said one source with direct knowledge of the decision.

Larkin has run successful campaigns for former mayor Sam Katz and was a key strategist in the Kirkfield Park byelection won by new MLA Kevin Klein (above). (John Woods / Winnipeg Free Press files)

So, what is Stefanson getting with this major personnel decision? Both Larkin and Diamond bring with them a wealth of experience, and some interesting political baggage.

Larkin has run successful campaigns for former mayor Sam Katz and — most recently — was a key strategist in the critically important Kirkfield Park byelection won by new MLA Kevin Klein.

In 2011, she teamed up with Tory Sen. Don Plett to chair the party’s provincial election campaign for then-leader Hugh McFadyen. By all accounts, the Tories ran an excellent campaign that resulted in a six-point bump in overall voter support.

Unfortunately, facing NDP incumbent Greg Selinger, the Tories were unable to win additional seats. McFadyen resigned as leader and Tories unfairly used Larkin and Plett as political pinatas.

Fast-forward to the summer of 2021 and Larkin appears again as a key force in the leadership campaign to replace Pallister. However, Larkin ended up working for Stefanson’s only opponent in that race, former MP Shelly Glover. Although it was a bitter fight, Stefanson clearly holds no grudges.

If Larkin is a constant presence in Tory politics, Diamond is a more elusive player.

He is a Winnipeg-born freelance political strategist who gained profile after managing Ontario Premier Doug Ford’s 2018 leadership campaign and advising the Ontario PC party’s 2018 and 2022 election campaigns.

In Manitoba, he advised mayoral candidate Jenny Motkaluk — but claimed no official role — in her two campaigns. And while Stefanson’s team denied that Diamond had any official role in her 2021 leadership bid, his biography claims he was a senior adviser on her campaign and served on her transition team.

Manitoba Premier Heather Stefanson is counting on strategists Marni Larkin and Michael Diamond to help her win re-election in the fall. (Matt Goerzen / The Brandon Sun files)

Sources said Diamond has pulled back from an official role with the Manitoba Tories’ re-election campaign after becoming the president of the Ontario PC party. Even so, the sources said he will continue to help Stefanson.

When leaders are forced to choose between warring factions within their stable of advisers, it can really only go two ways.

If Stefanson somehow pulls victory from the jaws of electoral defeat this year, she will be celebrated for her prescient political acumen.

If she is trounced, she will be the latest in a series of leaders who — faced with an existential political threat — wagered on the wrong horse.

Dan Lett

Dan Lett

Born and raised in and around Toronto, Dan Lett came to Winnipeg in 1986, less than a year out of journalism school with a lifelong dream to be a newspaper reporter.


Updated on Monday, January 23, 2023 8:15 PM CST: Corrects information to note Greg Selinger was premier in 2011

Updated on Tuesday, January 24, 2023 7:39 AM CST: Corrects typo

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