November 23, 2023

O’Leary: What’s next for the Bombers?

Thomas Srklj/

As we slowly move past the Winnipeg Blue Bombers’ crushing loss at the 110th Grey Cup, a harsh but simple reality is making itself felt to the organization, players and fans alike: winning is hard.

The Bombers need look no further than the likes of John Hufnagel and Dave Dickenson in Calgary, or to Wally Buono in his time in Calgary and BC as a head coach and general manager, where wins were aplenty over the years, but championship rallies and parades proved tougher to come by. The Bombers could have looked across the field this past Sunday and seen Anthony Calvillo — the CFL’s most productive quarterback ever — and remembered that he went 3-5 in Grey Cup games as a player.

In a nine-team league, in single-elimination playoff games, anything can happen. The league has produced two 16-2 teams; neither have made it to the Grey Cup game. In the last 10 seasons (2012-2023, accounting for the cancelled 2020 season), the team with the best record in the league has won the Grey Cup just four times (Winnipeg 2021, Calgary 2018, Edmonton 2015, Calgary 2014).

That means three 15-win teams (the 2022 Bombers, the 2019 Ticats and 2016 Stamps), a 14-win team (the 2013 Stamps) and two 13-win teams (the 2017 Stamps and 2012 Lions) have been left out in the cold after dominating the regular season.

» Dynasty Denied: Bombers drop second straight Grey Cup
» Three stats that defined the 110th Grey Cup
» Sign up and re-watch Grey Cup Week events for free on CFL+

A win on Sunday would have lifted this Bombers team into rare CFL air. Three Grey Cups in four years could nestle you in somewhere behind Edmonton’s five-in-a-row run of the late 1970s and early ’80s; who in Edmonton would argue that when Wayne Gretzky’s Oilers took four of five Stanley Cups later in the ’80s?

Instead, Cody Fajardo conjured up some legacy-defining magic of his own in the final two minutes of play, penning a new and final narrative on the 2023 season.

We give you all of that to drop another simple reality: this Blue Bombers team has had an incredible run, playing in four straight Grey Cups, winning in two and racking up wins and league awards over the last three seasons in particular.

Since the Bombers got back to Winnipeg, the local media has been all over the Bombers’ off-season outlook. For the first time since the team lifted that first Grey Cup in 2019, the Bombers face a uniquely challenging winter that could lead to a substantially different roster taking the field when training camp opens next spring. Let’s take a look at some of the key issues.


General manager Kyle Walters has assembled this powerhouse team and year-after-year his off-season process has been almost identical to the last. Players have hurriedly signed extensions, many of them before the calendar flips over to the new year. The bulk of them find their way to a sit-down with him ahead of free agency beginning in February and it’s not uncommon for players to take less money to find their fit with his team.

How, to paraphrase Michael Scott, the turntables. Walters’ contract is up this year and he and the organization put talks on hold earlier in the season to focus on the task that was at hand. With the off-season dawning on us, Walters and the Bombers will have to work to sort out things out. Bombers’ president Wade Miller told reporters last week that those talks would begin immediately, wrote Jeff Hamilton of the Winnipeg Free Press.

Hamilton also reported that Bombers’ assistant GMs Danny McManus and Ted Goveia are also on expiring contracts. Keeping that group intact could be a challenge, but the results yielded over the last four seasons speak for themselves.



Brady Oliveira emerged as a bona fide star this season, amassing over 2,000 yards from scrimmage, being named Most Outstanding Canadian Player and the West Division’s nominee for Most Outstanding Player. Just 26, Oliveira is obviously eying all of his options as he enters into free agency.

That includes exploring NFL opportunities. He confirmed that to Winnipeg media when the team got home this week.

“Playing here is a dream but the NFL stuff, ever since I started playing football was to play at the highest possible level,” Oliveira told The Canadian Press’ Judy Owen.

He’ll work with his agent to get those NFL looks and if that doesn’t pan out, the Winnipeg product made it clear that there’s no other uniform in Canada that he’d want to wear.

“If the NFL doesn’t work out, I want to be here in Winnipeg,” he said.

Like any team with a longtime returning core, the group is getting older. Retirements will factor into the off-season for every team across the league. In Winnipeg, offensive tackle Stanley Bryant wasn’t at Tuesday’s end-of-season availability to address his future. Jermarcus Hardrick told the Free Press’ Taylor Allen he’d have to think about what’s next for him. Zach Collaros will be back next year, but backup Dru Brown seems ready to roll with a team that would take him on as a starter, according to Postmedia.

Some of that talk, just days removed from a heartbreaking loss, can be emotionally driven. It’s a long off-season, with lots of time for wounds to heal and for players to fairly contemplate their futures.’s Ed Tait shared the team’s list of pending free agents this week and it’s a long, talented one, laced with key contributors, including five offensive linemen. The Bombers have shown they’ve been able to corral the bulk of these players before they hit the open market and perhaps they can do that again. This year seems like the most challenging out of the last five.

While the team fell short of its goal this year, we shouldn’t lose sight of what the franchise has done over these last five seasons and that it can still extend its magic into 2024. It’s easy to be spoiled by prolonged success and the expectations of championships. The Bombers have made it into the playoffs for the last seven seasons. Before that, the team had found the post-season just once in the previous seven years and carried a 29-year Grey Cup drought up to the 2019 season.

As a fan, you realistically hope your team is competitive every season and has a shot at winning it all. You know as well that even when that expectation is met, the window isn’t open forever. That’s a standard that the Bombers have lived up to and exceeded twice in the last four years. As they head into a potentially complicated off-season, that’s something to be mindful of and to appreciate.

The comment system on this website is now powered by the Forums. We'd love for you to be part of the conversation; click the Start Discussion button below to register an account and join the community!