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Mike O’Shea and the Winnipeg Blue Bombers are where Ryan Dinwiddie wants the Toronto Argonauts to be.

Winnipeg faces Toronto in the Grey Cup game Sunday at Mosaic Stadium. The Blue Bombers are chasing a third straight CFL title.

“I have a lot of respect for [O’Shea] and what they’ve done in Winnipeg,” Dinwiddie said Wednesday during the Grey Cup coaches news conference. “In years prior, Calgary was kind of the model everybody wanted to follow and I think now it’s Winnipeg.

“Calgary is still a great organization as well, they’re in the playoffs every year. But I think the chance to play in three Grey Cups in a row hasn’t happened since the Warren Moon days and that’s pretty impressive in this day and age.”

Winnipeg is vying to become the first franchise to win three straight Grey Cups since Edmonton captured five consecutive titles (1978-82). Moon was a member of all five teams, the last three as the starting quarterback, before heading to the NFL.

Winnipeg has been the class of the CFL since ending its 29-year Grey Cup drought in 2019. The Bombers have finished atop the West Division the last two seasons, posting league-best records of 11-3 and 15-3, respectively.

The 15 regular-season victories is a Winnipeg franchise record. The Bombers, though, have registered double-digit wins in each of the last six seasons under O’Shea, the ‘21 CFL coach of the year and a finalist with Dinwiddie for this year’s honour.

But the Bombers weren’t an immediate success under O’Shea and GM Kyle Walters, who took over on an interim basis in 2013 before being given the post full-time later that year. Winnipeg was a combined 12-24 during O’Shea’s first two seasons before posting an 11-7 mark to finish third in the West Division and reach the CFL playoffs.

Dinwiddie knows all about being part of a winning franchise. Before joining the Argos, he served as Calgary’s quarterback coach from 2016-19 when the Stampeders appeared in three straight Grey Cups (2016-18), winning the final one.

Dinwiddie said spending time with Stampeders president/GM John Hufnagel and head coach Dave Dickenson helped mould him as a coach. But so too has watching O’Shea handle his business and picking the brain of Argos running back Andrew Harris, who helped Winnipeg win its last two Grey Cups before signing with Toronto as a free agent.

“You take a lot from anybody you can learn from to make yourself better,” said Dinwiddie, who is completing his second season as Toronto’s head coach. “I have to give coach Huf and coach Dave a lot of credit, I learned a lot from them in Calgary.

“I’ve got to see what Mike got done in Winnipeg. Did he do it overnight? No, but look at what he’s built – a factory over there. You look at that and want to build that yourself. We’re playing in this game so I think we’ve made some positive strides as an organization over the last two years. You want to build that model that can sustain success for a long time.”

Toronto has finished atop the East Division standings in each of the last two years. After being dispatched by Hamilton in the ‘20 conference final, the Argos advanced to the Grey Cup with a 34-27 division final win last weekend over Montreal.

“[Dinwiddie] is a fiery competitor and his team is too,” O’Shea said. “You don’t get to this point, you don’t get to the final game unless you’re coaching details, both sides.”

O’Shea, the CFL’s longest-tenured head coach, said while he’s picked up elements from coaches he both played for and worked with, he hasn’t spent much time examining what makes other organizations tick.

“Obviously any interaction you have with coaches throughout the years from when you’re playing on the way through and up when you’re coaching on other staffs has the potential to leave an imprint on you,” he said. “But ultimately, you can only be who you are, right?

“I’m never going to be Pinball [Argos GM Mike Clemons], never. And if I tried it would not work. Authenticity is paramount. I don’t know that we have enough time in a day to study what other organizations and staffs are doing as much as really just looking in-house and figuring how you can make your place better.”

O’Shea and Dinwiddie locked horns as CFL players – O’Shea as an Argos linebacker and Dinwiddie a quarterback with Winnipeg.

O’Shea won three Grey Cups as a player with Toronto (1996-97, ‘04) and another as the team’s special-teams co-ordinator (2012). Dinwiddie started the ‘07 CFL championship game after Winnipeg starter Kevin Glenn was injured in the division final but the Bombers lost 23-19 to Saskatchewan at Rogers Centre.

“It’s unfortunate we weren’t able to bring a Grey Cup back to Winnipeg,” Dinwiddie said. “I really wanted to be one of the first guys to do it.

“Unfortunately, Mike was the guy who got it done.”

Both Dinwiddie and O’Shea agree their time on the field has given them insight into and an appreciation of what players go through.

“You hear certain people say, ‘The grass isn’t too far removed from the cleats,’ but I think coaching is a lot different,” Dinwiddie said. “The fact you have that background, you can relate to the players a little bit and understand some of the circumstances they’re dealing with.

“But if you see yourself kind of in that player mindset as a coach you’re not doing the right things.”

Added O’Shea: “There’s an element of understanding of what the players are going through. It allows you as a leader to be more empathetic to their situations … but there’d be no reference point to my career or Ryan’s probably. They [current players] are so far removed from that, they’re not really paying attention to that.”

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