Nothing came easy, that’s why this is so sweet

It was most likely the hardest Grey Cup ever won, and because of that, it will probably end up being the most rewarding too.

Read this article for free:


Already have an account? Log in here »

To continue reading, please subscribe with this special offer:

All-Access Digital Subscription

$4.75 per week*

  • Enjoy unlimited reading on
  • Read the E-Edition, our digital replica newspaper
  • Access News Break, our award-winning app
  • Play interactive puzzles

*Pay $19.00 every four weeks. GST will be added to each payment. Subscription can be cancelled anytime.

Hey there, time traveller!
This article was published 02/12/2019 (1159 days ago), so information in it may no longer be current.

It was most likely the hardest Grey Cup ever won, and because of that, it will probably end up being the most rewarding too.

There is a saying in life that without the bitter and sour, the sweet isn’t as sweet. You can’t fully appreciate what you’ve accomplished, without first mucking through the contrast of failure.

Fair comment then, that the Winnipeg Football Club and the fans that have stood by this team over the decades, are appreciating this win more than most anybody else has in CFL history.

The internet tells us that the Saskatchewan Roughriders own the all-time Grey Cup drought of 56 years—from 1910 to 1966—almost double the era of emptiness that Winnipeg escaped from, but this is the end of a story in Manitoba that will most likely never be repeated.

The Winnipeg Football Club and the fans that have stood by this team over the decades are appreciating this win more than most anybody else has in CFL history. (Nathan Denette / Canadian Press files)

When I first landed in Winnipeg in 2001, the drought was only 11 years old. By the end of my career, it was pushing 22 seasons, and we had failed to bring the cup home three more times.

It takes seasons spent in a city to understand the environment you’re in as a new player or coach. You don’t just sign with a team and immediately figure out the landscape of a new league and assume the burdens and experiences of the fan base and the franchise.

But it’s fair to say, by the middle of my career, I understood what the tarnish and stain of losing the big game was doing to this organization and its participants.

The longer a drought goes on, the more cynicism, skepticism and apathy grabs hold of you and becomes a part of your football filter. “Rebuilding,” sounds like yet another excuse for losing, instead of a way to change the culture and emphasis. “Continuity,” becomes another word for job security, instead of a different approach that allows in-house talent to develop. A locker room full of “character players,” sounded like a consolation prize and a Boy Scouts merit badge, instead of the building blocks of a team that is truly a brotherhood.

A championship drought is a dark cloud that shadows everything, good and bad, in its path. Once a team starts to win, and the pieces all come together, you realize only too late that it was all actually part of one hell of a plan.

Bombers head coach Mike O'Shea gets a sports drink poured over him after the team's Grey Cup victory. (Frank Gunn / The Canadian Press files)

As a former player who has been writing about this team since 2002, and talking about it on the radio — in one form or another — since 2006, by the time the rookie triplets of Wade Miller, Kyle Walters and Mike O’Shea showed up in 2013 and 2014, respectively, it was hard to believe things could or would be any different, let alone any better.

In my experiences, from 2001 to 2014, when the now-anointed, Canadian Mafia took the reins, this franchise had already chewed up its seventh different head coach, only two of whom had had any prior experience as head coaches in the CFL (Dave Ritchie and Jim Daly).

So when confronted with the inexperience of O’Shea as a frontman, and the newness that both Walters and Miller brought to the table as football executives, it was easier to envision ways in which they, too, would fail, instead of turning over a new page and believing in the possibilities that they could succeed.

Suffice to say, the championship this group, and this team, delivered in 2019, was quintessential Winnipeg. Not only did it take six seasons within a three-decade framework to get done, but it was as difficult to navigate as a pothole-marked street in the spring.

It can be hard to live in Winnipeg, and landing this Grey Cup had to be equally as challenging. Few teams can face the kind of adversity and obstacles that this one did, and be better off for it, and use it is a springboard into the playoffs.

Bombers president and CEO Wade Miller was inexperienced as a football executive before becoming the Bombers president and CEO. (Free Press files)

As the victory and celebration is fresh, you can still feel the collective exhale and sigh of relief in this province. It will be a while for this truly to sink in for many of us.

No longer is every team saddled with the failures and shortcomings of those that came before. They are now buoyed by and held to the standard of the most recent — and best football team in Canada.

No longer is every winning season marred or tainted by a statistical impossibility that the players can’t even fathom, let alone relate to.

Thanks to the efforts of all of those directly involved, the pride and passion of football in this community seems to have been restored, and anything seems possible. Whether that’s inspiring the next crew of future Canadian football all-stars and saviours— about to graduate from Oak Park High School — or the encouragement of more gutsy gambles, such as giving a fourth chance to a quarterback who had been written off by every football pundit and analyst in the country.

This franchise executed on its long-term strategy by every and any means necessary, with the interminable work ethic of its leadership and the undeniable talent of the players.

All that is left to debate now, is how far this championship season will resonate, and whether the Bombers can pull it off again.

Hope to see you all next season, when we get to find out.

Doug Brown

Doug Brown

Doug Brown, always a hard-hitting defensive lineman and frequently a hard-hitting columnist, appears Tuesdays in the Free Press.


Updated on Monday, December 2, 2019 8:18 PM CST: Fixes typo.

Report Error Submit a Tip