SIMMONS: Toronto never fully appreciated the success of Ryan Dinwiddie

Ryan Dinwidde won two Grey Cups in Toronto. That places him alongside Cito Gaston and Don Matthews as all-time bench bosses coaches.

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Published Jun 18, 2026  •  4 minute read

Ryan Dinwiddie, head coach and general manager of the Ottawa Redblacks, stands on the field during the team’s annual Fan Fest earlier this year. Ashley Fraser/Postmedia Network

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It is a very short list, Toronto coaches who have won more than one championship in the city.

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Cito Gaston won the World Series twice. The late, great Don Matthews won the Grey Cup twice with Doug Flutie as his quarterback.

Alongside them, rather quietly, are the two Grey Cups won by Ryan Dinwiddie — who was never fully celebrated much for all he accomplished in his time with the Argos.

Part of that was his personality and where the Argos sit on the sporting landscape. He didn’t affect people the way a Matthews or a Gaston did. He wasn’t a big personality. He should have left a lasting impression, but somehow never did.

You just don’t think, ‘Ryan Dinwiddie, legend.’ But maybe you should.

He won the Grey Cup with the Argos in 2022, led the team to it greatest regular season in 2023, tying the most wins in league history at 16, winning the Grey Cup again in 2024.

These are all-time kind of numbers — not necessarily appreciated as they should be.

But as Dinwiddie departed this past November for the coach and general manager job with the Ottawa Redblacks, he did so without much noise or fanfare — which is kind of how he coached the Argos in his five seasons here.

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And now on Saturday afternoon at TD Place Stadium, the former Lansdowne Park, Dinwiddie will look across the field and see his former assistant coach and friend, Mike Miller, now the head coach of the Argos, and see the all-star quarterback he went to war for and with, Chad Kelly, who lives just down the street from him in Toronto.

Kelly all dressed in the Double Blue of the Argos on one sideline, Dinwiddie coaching the home team Redblacks on the other.

“I don’t know what I’m going to feel,” Dinwiddie said on the phone. “You try not to get emotional about all this because I’m so focused on our football team and trying to get us a win.

“I know a lot of guys over there, especially on the offensive side of the ball. It was tough (to decide to leave). I have a lot of love for a lot of those players and people.

“I was treated very well by the Argos. I brought my family to Toronto. We lived there. My kids go to school there. We enjoyed the city.

“It was home for us.”

CFL’s coaching circle a tight-knit group

Kelly, the often-controversial quarterback, lives just down the street in Toronto. He remains one of the highest-paid players in the CFL. He likes to occasionally play with Dinwiddie’s kids. That’s how close the relationship is.

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The CFL is probably the most unusual of almost major leagues. There is a family kind of atmosphere to the league. Dinwiddie coaches the Redblacks. His former quarterback coach, Murray, is now head coach in Toronto. His former defensive coordinator, Corey Mace, has his own Grey Cup as Saskatchewan’s head coach. That’s one third of the league.

Hamilton’s coach, Scott Milanovich used to coach the Argos. On his staff one year he had young coaches Mike O’Shea, Jason Maas and Orlondo Steinauer.

O’Shea is now considered the best coach in the CFL in Winnipeg — and was the Argos target before they settled on Miller. Maas has won a Grey Cup as head coach in Montreal. Steinauer, no longer coaching, went to two Grey Cups when he was head man in Hamilton.

No other league operates like an extended family picnic. Everybody knows everybody in the CFL. But the challenge remains the same: To win games, to establish yourself and your team, to win the Grey Cup.

Why did Dinwiddie leave Toronto?

Last November, the Redblacks reached out to the Argos and asked for permission to talk to Dinwiddie.

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Under CFL rules, because Dinwiddie was a head coach, Ottawa needed to offer a promotion in order to speak with him. Dinwiddie had long wanted to be a general manager. When the offer came, he didn’t take a lot of time to answer.

He grabbed the opportunity, took the promotion and left for Ottawa.

“We had a close football team and a very close staff in Toronto,” Dinwiddie said. “I think we all learned from each other. It’s important to do that and have that.

“I started fresh in Toronto and now I’m starting fresh here. The opportunity to work with Shawn Burke (head of football operations for the Redblacks) made this enticing. I’ve always had great respect for him.”

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The CFL is a quarterback’s league. Toronto has Kelly. Hamilton has Bo Levi Mitchell. Montreal has Davis Alexander … Ottawa takes a step back with Jake Maier as its starter.

But Dinwiddie got to his first Grey Cup with McLeod Bethel-Thompson as his quarterback so, really, anything is possible.

And this is just the beginning, really for the almost Toronto legend.

He can’t get too caught up in who he’s playing against on Saturday afternoon. As George Allen used to say, the future is now for the new coach in Ottawa.

The past, though, is more than memorable.

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