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May 22, 2020

In conversation with O’Shea about success, upcoming season

Earlier this week, yours truly had the chance to have a Zoom conversation with Mike O’Shea, and during our long chat we riffed on a number of different subjects.

We talked about what was scheduled to be the opening of Winnipeg Blue Bombers training camp this weekend, about the Snowbirds fly-by over our city on Tuesday, about our families, and about the head coach’s belief in the resiliency of the Canadian Football League.

One of the ideas I also wanted to explore was the Bombers’ attempt to repeat as Grey Cup champions – whenever that quest may begin – and how coaching a team with that goal, compared to chasing a title in the midst of a decades-long championship drought, like last year, might present different challenges.

This notion had been banging around in my cranium all winter, and was then further fuelled while watching ‘The Last Dance’ mini-series about Michael Jordan and the Chicago Bulls over the last few weeks.

‘The Last Dance’ has reinforced and rekindled a few talking points for those who remember that era, from the stone-cold killer Jordan was on and off the court, to how unappreciated Scottie Pippen was during the Bulls’ run, to the bizarreness of Dennis Rodman.

It also showcased Phil Jackson’s uniqueness and skill as a coach, from managing the ego and greatness of Jordan, to giving Rodman the freedom to do his thing, to managing the anger of Pippen as he fought for respect from his own organization, to operating under the thumb of GM Jerry Krause, who made no secret of his desire to punt him from the Bulls’ bench the minute his contract expired.

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Amidst all that, the Bulls won. They won a lot. And Jackson also worked through the challenge of taking a team that was close to the winner’s circle to a title and then through the attempt to repeat again and again.

All that formed part of the backdrop during my chat with O’Shea, who warmed up to exploring the subject.

“I don’t know that we spent any time talking about ending the drought last year,” began O’Shea, “And I don’t know if we’ll spend a lot of time talking about repeating, either. In either set of circumstances you just talk about how you are going to win a championship.

“The word ‘repeat’ will be brought up and talked about by a lot of other people. If we happen to succeed that word will be used. But in our building, in our meeting rooms, that’s not how we’re going to talk.”

That, in less than 100 words, is classic O’Shea. His approach has always been to coach in the moment, all the while keeping the eyes on the bigger prize.

Clearly that template worked last season, and was evidenced in the ‘Road to the Grey Cup’ documentary when just prior to the Western Semi-Final win over Calgary, O’Shea is heard telling the group “… everything we’ve done up to this point has turned you into a smarter, hardened football team. You’re ready for anything… You’re ready, fellas. You’re ready. Love every moment of this, take it all in.”

And Bomber Nation is still re-living what unfolded that day and on the following two Sundays.

O’Shea runs onto the field at the 107th Grey Cup presented by Shaw in Calgary last November (

Still, I wanted to explore this a bit further with O’Shea and asked him if he was doing any reading on coaching to repeat, or if he drew inspiration from some of Phil Jackson’s philosophies or that of any other coach.

“Well, Phil Jackson is a hall of fame coach but if you asked him to step into our building it would still take him time to get a sense for what’s going on, what these players need and how to coach and manage them,” said O’Shea. “Our staff is best suited to figure out what our team needs as opposed to reading someone else’s manual on what their team needed. Obviously, there’s great information in that and I am always trying to learn. But I want to keep what we do as ours.

“Every team is different and with that, as coaches we have to quickly figure out what those differences are and then what are the requirements we have to give the players and then managing the differences to get to where we want to get to.

“I don’t know if there’s a book that has a prescription for every single thing that’s going to happen to this version, the 2020 version of the Bombers. That would be a huge book… you’d read to the bottom and it would be, ‘Jump to Page 70 and if this is the outcome jump to Page 76, then back to Page 34.’ Again, every team is different.

“This year everybody will be so bloody happy to be back in the building and be at work there will be no magic word needed to motivate them. They will be stimulated across everything. That’s across any league in any sport: they will be just so pleased to be back in the dressing room.”

O’Shea talks to his team during a practice (

Ultimately, that’s the key message O’Shea will deliver whenever his football team gathers together again: last season was a helluva story and – as he said after the Grey Cup win – it’s a story that should be told for years to come.

But what happens next won’t be about repeating, it will be about writing a new chapter. Some of the faces and storylines will remain, many will be different.

And in that approach, O’Shea and Jackson are essentially the same, although they undoubtedly deliver their messages differently.

In his book ‘Eleven Rings: The Soul of Success’ Jackson wrote:

“There’s a Zen saying I often cite that goes, ‘Before enlightenment, chop wood, carry water. After enlightenment, chop wood, carry water.’ The point: Stay focused on the task at hand rather than dwelling on the past or worrying about the future.”

O’Shea knows a lot about the soul of success, too, as a five-time Grey Cup champion – three titles as a player, two more as a coach. He’s also big on hammering home the simple message of hard work, and each player doing their job.

So, from that perspective, he’d be all in on the concept of chopping wood and carrying water.

“A lot of the things we went through last year were one-offs that I’ve never seen happen before,” O’Shea said. “There will be a whole new set of one-offs and there will be some stuff that we see happen every year.

“I do honestly believe that the way things shook out last year was perfect. And we’re going to find a way to make it perfect again this year under a whole new set of circumstances, a whole new set of events.”