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A Rocky day on the mayoral campaign trail for Kevin Klein

Kevin Klein acknowledges it’s hard to foresee what he’ll wake up to each morning in the final weeks of a mayoral campaign.

But the seasoned politician, who has served as both a city councillor and a provincial cabinet minister, couldn’t have predicted the events — what he describes as “drama” — that unfolded last Sunday.

Fellow mayoral candidate Mike Vogiatzakis accused Klein’s campaign team of offering him a job to drop out of the race, while a guest writer’s column in the Winnipeg Sun that questioned the deaths of Indigenous children at residential schools, just days after the National Day for Truth and Reconciliation, sparked condemnation from a prominent Indigenous organization. (Klein is the CEO of the Klein Group, the company that owns the Sun. He has maintained he is not involved in its operations while running for mayor.)

The Free Press had already been scheduled to join Klein on the campaign trail Monday, intending to document a day in the life of the front-running candidate to unseat incumbent Scott Gillingham, before the controversies hit.

Longtime voice of the Blue and Gold marks major milestone

Bob McGregor made his debut as the Winnipeg Blue Bombers’ public-address announcer on June 7, 1997, during a pre-season game at Winnipeg Stadium between the hometown Blue Bombers and their western rivals, the Calgary Stampeders.

McGregor will be behind the microphone again this Saturday, detailing the action on the field in addition to leading a boisterous Princess Auto Stadium crowd through what has become his signature call, “And that is another Winnipeg Blue Bombers first down!”

The Bombers’ final home date of the 2026 regular season will mark a major milestone for McGregor, and the former newscaster feels it’s only fitting the same two teams as 10,717 days ago — the Bombers and Stampeders — will be the ones butting helmets.

“I knew at the start of the season I was closing in on 300 games as the PA guy, only it wasn’t until I went through the schedule that I realized my 300th would be Winnipeg-Calgary, which struck me as kind of cool,” McGregor says, seated in a St. James breakfast nook, dressed in dark trousers and a blue-and-gold Blue Bombers golf shirt.

Musk’s meddlesome trolling

It seems obvious the world’s first trillionaire thought he was helping separatists within the Canadian federation when he encouraged three provinces — Alberta, Saskatchewan and Quebec — to leave Canada.

Unfortunately for Elon Musk, a man suffering from a profound deficit of self-awareness, his comments may only help those who want to keep the country together.

Musk entered the national unity debate on Wednesday, two days after the pro-independence Parti Quebecois was returned to power in Quebec with a minority mandate. The PQ has promised to hold a third referendum on separation at some point in its current term.

Musk — who has a Canadian mother and attended university in Ontario — took to X, the social media platform formerly known as Twitter (which he owns) and encouraged Quebec to forge ahead with plans to separate. He said Alberta — which will hold a vote this fall on whether to hold a binding referendum on separation — and Saskatchewan should follow suit.

Dozens of Uber, Lyft drivers switched to cheaper insurance coverage: MPI probe

Ride-service drivers have been defrauding Manitoba Public Insurance by improperly insuring their vehicles as for personal use.

The public insurer and the City of Winnipeg, which regulates ride-hailing services like Uber and Lyft, discovered the widespread fraud after MPI conducted a review in December last year.

“When a driver changes their coverage from ride-share insurance to a personal vehicle coverage and continues to operate as a ride-share driver, that is fraud, plain and simple,” said MPI chief executive officer Satvir Jatana at a news conference Thursday.

MPI’s review looked at a random sample of 408 ride-hailing vehicles and found 108 were operating without the proper vehicle-for-hire insurance coverage. In order to register with the city as a ride-service driver, a vehicle must have such insurance and proof must be provided to the ride-booking company.

Other cities build rapid transit, while we wait

Winnipeg’s civic election campaign has produced no shortage of promises to improve transit safety and fix problems with the new network. Those issues are real and urgent. But they should not distract from a larger failure — while other Canadian urban regions secure billions in federal support to transform their transit systems, Winnipeg is falling further behind.

Yielding attraction

Yield is a Rorschach test for investors. Where one see opportunity in high payouts from an investment, another sees high risk.

Consider bonds: yields are moving higher, which implies higher risk in the market, but to an investor considering buying a bond, higher yields represent higher income.

For most of the past 18 years, bond yields have been near historical lows and investors have sought alternatives.

“Canada’s population is aging, with a growing number of investors approaching or entering retirement and looking for more income,” says Pat Sommerville, co-chief executive officer of Hamilton ETFs in Toronto.