29 Years of Hurt, Five Straight Grey Cups — and Now, Win or Go Home

Week 21 of the 2025 CFL season arrives with the Winnipeg Blue Bombers in a position that would have been unthinkable a half-decade ago: needing a result against the B.C. Lions to keep their season alive, with the playoff fates of Winnipeg, Saskatchewan and Calgary all knotted into the same final weekend. A 35-27 loss in Edmonton and a 33-28 survival against the Stampeders have left Mike O'Shea's club in a win-or-go-home scramble — the same franchise that played in five consecutive Grey Cups between 2019 and 2024.

For a team that spent 29 years trying to get back to the big game, the irony is sharp enough to cut. The Bombers know better than anyone in the CFL how quickly a dynasty can curdle into a drought — and how long a drought can last once it settles in.

The Long Winter: 1990-2018

On Nov. 25, 1990, at BC Place, the Blue Bombers demolished the Edmonton Eskimos 50-11 to win the 78th Grey Cup — still the most lopsided championship game in CFL history. Mike Riley was the head coach, Tom Burgess the quarterback, and the victory delivered Winnipeg its tenth Grey Cup. It looked like the continuation of a tradition: Bud Grant had won four titles in six appearances between 1957 and 1966, and the club had added rings in 1984 and 1988.

Nov. 25, 1990: Winnipeg 50, Edmonton 11 — the largest margin of victory in Grey Cup history. The next 29 seasons produced four Grey Cup losses and zero wins.

What followed was a masterclass in near-misses. In 1992 the Bombers lost 24-10 to Calgary at SkyDome; in 1993 they fell 33-15 to Edmonton at McMahon Stadium. The franchise bottomed out financially and competitively through the late 1990s, then resurfaced behind Khari Jones, only to lose the 2001 Grey Cup 27-19 to Calgary in Montreal. In 2007 — the year the drought's midpoint passed — Winnipeg lost 23-19 to Saskatchewan in Toronto, the most painful of the four defeats. In 2011, a 10-8 team rode a remarkable season all the way to BC Place and lost 34-23 to the Lions.

Then came the floor. The 2013 Bombers went 3-15, playing their final season at Canad Inns Stadium while the new stadium project on the University of Manitoba campus spiralled. David Asper's original "The Elms" development had collapsed in 2009 when his Creswin Properties could not secure financing; the province and the university stepped in through Triple B Stadium Inc., and Investors Group Field finally opened in June 2013 — a year behind schedule and well past its original $115-million budget. The building that was supposed to save the franchise nearly buried it first.

The turnaround began quietly. Wade Miller took over as president and CEO in 2013. Kyle Walters became general manager. And in 2014, a first-time head coach named Mike O'Shea was hired — a decision that looked unremarkable at the time and now stands as the most important in modern franchise history.

How the Drought Ended: The 2019 Run

The 2019 Bombers finished 11-7, third in the West, and nobody outside Manitoba gave them much of a chance. Then, at the October trade deadline, Walters acquired quarterback Zach Collaros from Toronto for a conditional draft pick — a journeyman who had been traded twice in eight months and was, at that moment, a backup.

Collaros started the Western Semi-Final in Calgary, where the Bombers had lost the 2018 West Final. Winnipeg won 35-14. A week later they went into Mosaic Stadium and beat the Roughriders 20-13. On Nov. 24, 2019, at McMahon Stadium, they beat the Hamilton Tiger-Cats 33-12.

Three playoff games, three road wins: 35-14 in Calgary, 20-13 in Regina, 33-12 in Calgary. The drought died on the road.

Andrew Harris, the Winnipeg-born tailback who had spent his career chasing exactly this, ran for 134 yards and was named both Grey Cup Most Valuable Player and Most Valuable Canadian — the first player to sweep both awards since the format changed. Willie Jefferson and Adam Bighill led a defence that suffocated Hamilton's offence. O'Shea, five years into a rebuild that had tested every ounce of organizational patience, had his first ring as a head coach.

The drought was over at 29 years — the longest in franchise history, and one of the longest in CFL annals.

Five Straight Finals — and the Reckoning

The 2020 season was cancelled by COVID-19, which makes what followed even more remarkable. Winnipeg won the 2021 Grey Cup 33-25 in overtime over Hamilton at Tim Hortons Field — the first back-to-back champion since Montreal in 2009-10 — then returned to the final in 2022 (a 24-23 loss to Toronto), 2023 (28-24 to Montreal) and 2024 (41-24 to Toronto). Five Grey Cup appearances in six seasons is a run matched only by Edmonton's six straight from 1977 to 1982.

But dynasties have a cost. The 2025 season has been the hardest since the rebuild began: a loss in Edmonton in which the Bombers were run over on the ground, an offence that has leaned heavily on Brady Oliveira, and a Week 21 date with the Lions that is effectively a play-in game. The same club that once couldn't buy a playoff berth now can't afford to miss one.

What fans should take from the last three decades is that droughts are not broken by luck. They are broken by infrastructure — a general manager, a coach, a stadium, and an organization willing to absorb four years of mediocrity before the payoff. The 2013 stadium crisis and the 2019 Grey Cup are the same story told at different ends. And the current fight, uncomfortable as it is, is the natural price of five straight trips to the final: the roster ages, the rest of the league catches up, and the margin shrinks to a single November afternoon.

The Bombers of 1990 could not have imagined 29 years of waiting. The Bombers of 2025 know exactly what it costs to avoid it.