O’Leary: Grey Cup sheds new light on CFL’s most mysterious man

Mike O’Shea listened to the question — sorry, The Question — and sat with a smile on his face as he watched his good friend tackle it first.

Orlondo Steinauer’s advice to his players regarding sex during the week of the Grey Cup was simple: Do what got you here.

The crowd that sat in front of them on Wednesday morning had debated how this would unfold. Would O’Shea engage on The Question? Or would he treat it like many of the regular, lower-case questions he faces in the day-to-day of his job?

Wednesday was not like any other day in the six years that Mike O’Shea has been the head coach of the Winnipeg Blue Bombers.

He listened to Steinauer and when it was his turn to answer he sat back in his chair and exhaled. You sensed a confucius moment coming.

“Well,” he began.

“It’s been eight years since we climbed into this position.”

There were a few giggles in the crowd.

“And another 29 since we finished the job. So there’s going to be some nerves.”

Steinauer cracked a smile and turned his head away.

» Bombers pushing to put championship drought to bed
» Morris: Harris, Bighill back in the big show eight years later
» Morris: Bombers cherishing every moment on road to Grey Cup
» Grey Cup Game Breakers: 10 names to know for Sunday


“And the expectations will be very high. And the anticipation can sometimes ruin the event. So I guess my guidance to the players would be don’t exhaust yourself in the warm-up.”

Steinauer laughed, pointed to his friend, then led the applause. O’Shea didn’t just engage in The Question. He provided one of the best answers it’s ever gotten.

That answer gave a glimpse to a side of the coach that those who ask O’Shea those daily questions very rarely see.

“I honestly think that that’s why you appreciate the way he was (on that stage), maybe more than most people in there would,” says Ted Wyman, the sports editor at the Winnipeg Sun and the Bombers’ beat writer since 2016.

“That was truly Mike O’Shea showing his colourful side, showing his personality. Being pretty talkative. That’s not the usual.”

“I just wish he was like that more often. He’s capable of doing it but he chooses not to,” said Winnipeg Free Press sports writer Jeff Hamilton, who has covered the Bombers since O’Shea was hired, back in 2014.

Over the six years that he’s been the head coach of the Winnipeg Blue Bombers, a Mike O’Shea press conference has become something of a show within the show of following the team.

There may be no coach in the CFL that’s more guarded than O’Shea. He swats questions about injuries away like they’re flies in front of his dinner plate. Questions about his game day roster are often met with a “We’ll see” or an acknowledgement that the team doesn’t have to release roster info until the day before the game, so that’s what he’ll do.

He doesn’t like to revisit his playing days. He prefers team concepts over individuality. Lighthearted questions are met with a shrug sometimes and where another coach might shrug, laugh and share something, O’Shea lets his shrug put a bow on the question up and open the window to the next one.

This might be the most unique media situation in the league. O’Shea doesn’t come across as hostile or contentious. Some coaches — Steinauer’s predecessor as head coach in Hamilton, June Jones comes to mind — are open books. With O’Shea, the book is laid on the Bombers’ press conference podium, closed shut and it takes a lot to pry it open, even a little bit.

In a way, it’s sort of an ultra-Canadian moment. There’s a coach that politely doesn’t seem to want to reveal anything and a media corps whose job by definition is to unearth truths, to ask the difficult questions, but is trying to do so in a tactful way. You get the sense watching these exchanges that there’s a cordiality to it, that even if it’s wire thin, along that fine line there is a happy medium to be struck; even if the balance to be found is now a six-year search.

“(It’s) challenging, which makes it fun,” says Winnipeg Sun columnist Paul Friesen, who has been around the Bombers since 1991.

“He’s not an easy interview. He’s not what you would call a quote machine, unlike our hockey coach right now. There are days when you can walk into the Jets without a (story) idea and come out with some Paul Maurice gems.

“With Mike, you’ve got to work for it and that’s OK with me. I kind of enjoy our back and forth, even though he’s not giving you a lot. I don’t mind that. I know he sees it as no benefit to his bottom line, which is winning. So I can understand that and respect that.”


One thing that the Winnipeg media learned quickly in the O’Shea era was that certain words elicit a specific response.

“If you were to say use the word, ‘effort’ and you meant performance, he would pounce on the word effort and not answer the rest of the question,” Wyman says.

“He’d say, ‘I will never say anything about our team’s effort. Our effort is fantastic.’

“It’s not really the question that you wanted to ask but he will seize on things…and particularly if you use words that you know that he doesn’t like, you’re going to get that problem.

“It’s your responsibility to know how to engage him and get him to engage back.”


Winnipeg reporters will sit in the media room at IG Field before O’Shea is there and think about how they want to word their questions. They want to avoid the pitfall phrasings while hopefully coming across something that will at least start to pry that closed book open a little bit.

“Sometimes you wrap your tongue around it rather than your head,” Wyman says, laughing. “Then if you say it wrong, it doesn’t work.”

“If he’s got an out, he’ll take it,” Hamilton says.

“He doesn’t like to get personal. He doesn’t like to share stories. It’s not that he’s never done it, but more often than not he just refuses to talk about his history playing. He refuses to talk about the accomplishments he’s made.”

When O’Shea went into the Canadian Football Hall of Fame, Hamilton had to take the long way to find a suitable story to commemorate the milestone. When O’Shea didn’t want to delve into his past, Hamilton went to O’Shea’s alma mater, Guelph University, and found people close to him  to help tell his story.

“I got this glimpse of Mike O’Shea (through that story) that I’ve never experienced,” Hamilton says.

“That whole experience to me was kind of epitomizing because he wouldn’t even do a story. He wouldn’t even do a one-on-one with anybody. He just didn’t want to talk about that moment where he was about to get honoured for his career. He had zero interest and never wanted to make it about himself.”


Across the Winnipeg sports media landscape, no one has the relationship with Mike O’Shea that Bob Irving does. The voice of the Blue Bombers on CJOB since 1974 — the media centre at IG Field bears his name — Irving hosts one of the few remaining coaches call-in shows left in Canada. Every Monday during the Bombers’ season, O’Shea meets Irving at the CJOB studios to talk about the team’s season while taking calls from fans.

“He’s down to earth. He’s quite guarded,” Iriving says of O’Shea.

“But when you get to know him and I’ve gotten to know him a little bit, certainly more than the other guys because of the fact that we have a weekly call-in show, he’s just a real first-rate human being, the kind of guy that you pull for.

“I do, anyway, because he cares deeply about football in Winnipeg. He knows how important it is. He’s a good family man and loves living in Winnipeg. All of the stories about him wanting to go to Toronto, I’ve gotten no indication at all that he wants to do that. He wants to win and I think stay in Winnipeg.”

Irving looks at O’Shea’s tenure in Winnipeg and sees a coach that’s created a culture of winning.


“The players respect him in a way that…Cal Murphy and Mike Riley and those guys were respected,” he says. “The players respect Mike enormously.”

The format of the show is straightforward. O’Shea arrives, Irving kicks the show off, he’ll ask a few questions and as the texts come in from fans, they’ll open the phone lines. The setting — just Irving and O’Shea in the studio chatting — likely helps put the coach at ease, Irving admits.

“When we do our show on Monday nights, he’s much more conversational but he’s much more comfortable in that forum, as opposed to 15 guys sort of peppering you with questions,” he says.

Irving has watched as the show has run through its allotted time, with calls still waiting to make their way to them. He says many times, O’Shea has stayed after and chatted on the phone with callers that didn’t make it to air.

“He says, ‘Hey, these people took the trouble to phone. The least I can do is give them an answer.’ It’s kind of cool,” Irving says. “That’s one of the things that impresses me, he sort of gets it. He doesn’t reveal a lot of things, but he gets it. He understands.”

If you’re one of the people tasked with asking O’Shea questions, that’s where frustration can set in. Every once in a while in Winnipeg (and on Wednesday here in Calgary), he’s shown those glimpses of being more than capable with a microphone in front of him. Talk to his players about him, talk to people around the league about him and you see someone that’s highly respected.

“The one thing that I notice is that if you talk to players, if you talk to people in the organization, they’ll say he’s the greatest guy you’ll ever meet,” Wyman says.

“A lot of people will say that. Players will say he’s one of the greatest coaches but that generally doesn’t come across in an interview setting, or especially from the podium.”


Jim Barker laughs as the topic of O’Shea as an interview subject comes up. Currently an offensive assistant with the Hamilton Tiger-Cats, Barker hired O’Shea to work on his Toronto Argonauts staff in 2010. It was O’Shea’s first coaching role and he flourished in it, landing the Bombers head coaching gig four years later.

“Behind closed doors, O’Sh is personable, he’s out there, honest and that’s what makes him a great coach is that he’s all those things,” Barker says.

“I think he’s not as comfortable in front of a camera or talking to media and things like that as (Steinauer) is.”

Watching O’Shea deal with media, whether it’s in Winnipeg or anywhere else in the country, you get the feeling that he’d just about rather be anywhere else. He was a player that pumped hours of prep time into film and he’s no different as a coach. However long the time is, you can bet that O’Shea would rather spend it on something that would help his team win.

“Mike O’Shea would probably rather do anything in the world than spend five minutes in front of the media,” Barker says, laughing again.

“But he understands that it’s a part of what makes this league go. He loves the Canadian Football League. But if he had his druthers, he would rather be doing anything else.”


Hamilton remembers in the early days of O’Shea’s time in Winnipeg, when he’d take a question and say that he doesn’t think about things that way. Hamilton rolled his eyes at first, but as the years have piled up he’s wondered if there’s something to that.

“For the longest time I thought, ‘No, everybody thinks that way, it’s impossible that you don’t think that way,’” he says.

“But over time, over the years covering him, I’ve come to truly believe that he thinks differently than a lot of people and his answers reflect that.”

Wyman jumps in here and brings up an interesting point.

“That was truly Mike O’Shea showing his colourful side, showing his personality. Being pretty talkative. That’s not the usual.”

Ted Wyman, Winnipeg Sun on O’Shea’s head coaches press conference address


“He also says, ‘We don’t think that way.’”

“That’s the thing, too,” Hamilton says. “When he’s speaking to you, he’s sending a message to his players. He knows his players watch those interviews. He’s always on point, he’s always on message, he’s always delivering that message.

“He uses that platform, which doesn’t do (media) a great service as far as getting answers but it does him a great service, to tell his players what his message is.”

“But let’s be fair,” Wyman adds. “It’s not his responsibility to give us the answers we want. It’s his responsibility to give us answers.”

It’s been an interesting dance, watching O’Shea navigate the Winnipeg media and vice versa.

Friesen, who has done an exceedingly good job of asking difficult questions of O’Shea and the team at times over these six years, has similarly gone back and forth on what it’s all meant. The two seem (at least to this observer that’s witnessed some of their exchanges) to have a mutual level of respect.

They’ll sometimes exchange simple greetings at the start of a media availability, or share a quick joke between questions. Friesen mentions that on slower days during the season, if he’s the only reporter that puts his recorder on the podium or the table that O’Shea is speaking at, the coach will hand him his recorder when the session is over and everyone’s getting up to leave. It’s a small thing, but a nice one.

Friesen doesn’t feel that he knows O’Shea on a personal level. “He reveals almost nothing, personally,” he says, “but you get a sense, looking another person in the eye.”

Last week, after the Bombers had defeated the Riders in Saskatchewan, O’Shea stood up to leave the press conference and Friesen met him at the table to get his recorder. He looked at Friesen and in the way that so many of us do when we’re parting ways with people that we work with or around, he said, “I’ll see you Calgary.”

The coach paused for a second and it almost felt like he needed to re-establish a boundary, maybe out of familiarity, maybe for his own comfort.

“Or hopefully not,” O’Shea said as he walked away.

The reporters talked about it later that night over dinner, trying to make sense of it. Six years in, Mike O’Shea is still very much a mystery.