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Published Nov 06, 2025 • 4 minute read
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Before the 2022 Grey Cup game, Winnipeg Blue Bombers head coach Mike O’Shea (left) and Toronto Argonauts head coach Ryan Dinwiddie attended a media event. Dinwiddie’s exit from the Argonauts has raised speculation that O’Shea might replace him. Photo by Heywood Yu /The Canadian PressArticle content
The Winnipeg Blue Bombers’ off-season just received a high-voltage jolt of intrigue.
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As head coach Mike O’Shea, the face of the franchise, approaches the end of his contract, another CFL job that would fit him like a glove opened late Wednesday.
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Ryan Dinwiddie’s surprise move from Toronto to Ottawa, where he adds the GM duties to his head coaching role, leaves the Argonauts in need of a head man.
I’ve always thought there were two places O’Shea could land if and when his time in Winnipeg runs out, either by his choice or someone else’s: Hamilton or Toronto.
Hamilton, because that’s where he started his CFL playing career and because, much like Winnipeg, it’s his kind of town with his kind of fans.
Toronto doesn’t have the lure of a widespread, passionate fan base, but it is where O’Shea played the majority of his career and where he started his coaching career, winning three Grey Cups as a player, one as an assistant coach.
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More importantly, it’s where Michael (Pinball) Clemons works.
Clemons was the Argos head coach when O’Shea won a championship there as special-teams coordinator in 2004. Before that, they won two as Toronto teammates.
Ask Clemons, now Toronto’s GM, about O’Shea and his eyes light up like, well, like a pinball machine.
These two don’t just respect each other, they love each other.
Clemons’ favourite line when people ask him about his favourite player of all time. “I don’t have favourites but Mike O’Shea is my favourite.”
Days before his Argos took on O’Shea’s Bombers in the 2022 Grey Cup, Clemons expanded on his feelings about his fellow Hall of Famer.
“He is one of the most special people that I’ve ever been around in my life,” Clemons said. “Love him like a nephew, brother, son – whatever you want to call it. He’ll always be one of the most impactful people in my life.”
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O’Shea’s comments about Clemons that same week glowed just as warmly.
“He taught me a tremendous amount,” the coach said. “He’s one of the best human beings you’ll ever meet. I love the guy.”
Love, meet loyalty.
We can only imagine the conflicting emotions within O’Shea when he gets that call from his old boss and teammate – if he hasn’t got it already.
The CFL prohibits teams not in the Grey Cup from making any big announcements from Thursday of this week through Grey Cup Sunday. The Argos came in just under the wire with their news on Dinwiddie.
Theoretically, they can’t even talk to O’Shea, yet. He’s still under contract.
But nudge and wink your way into denial all you like.
Toronto can ask for Winnipeg’s permission to talk to O’Shea before his contract expires if, say, they’re offering him a promotion, like the one Dinwiddie got in Ottawa.
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Even if they’re not, what’s a little get-together between old friends?
So get ready to unleash the paparazzi for Grey Cup week. Scour the restaurants and bars, the side streets and back lanes, for the Royal Couple. I can see the tabloid headlines already: The two Michaels: Will they reunite?
In his season-ending media session the other day, I asked O’Shea if he was ever intrigued about the idea of a new challenge.
“I don’t offer myself a lot of time to think about other things,” he said.
He repeated how much he loves the fans here, and why not, after 13 straight sellouts.
A new challenge in Toronto? That’d sure be one.
The 55-year-old’s first love is the CFL and making football matter again in Toronto would be great for the league. Then again, not even winning two of the last three Grey Cups could accomplish that.
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Asked if he could give fans any sense of where he planned or hoped to be: “Well, I’ve been here for 12 years. I haven’t left yet. I’ve always said this is a great community. People that just pass through don’t understand it. People that spend any amount of time here realize how good of a city it is and community it is.
“In terms of a sporting community, it’s awesome.”
Perhaps that will be enough for Winnipeg to keep him.
Maybe Bombers president/CEO Wade Miller will have to up the ante and match whatever Clemons has in mind.
I’ve heard from some fans who think it’s time for a change. They have no idea what’s on the other side of that.
O’Shea is the No. 1 reason this team’s culture is what it is. Eight straight playoff appearances, five trips to the Grey Cup and two championships is the result.
In the days after the Bombers lost their playoff game in Montreal, players were asked if this was the end of an era.
Every single one said no.
That answer would change if their head coach bolts.
We’ll leave you with the words of linebacker Redha Kramdi.
“The Winnipeg Blue Bombers wouldn’t be the Winnipeg Blue Bombers without Michael O’Shea.”
paul.friesen@kleinmedia.ca
X: @friesensunmedia
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