The Saskatchewan Roughriders organization is celebrating yet another Grey Cup victory, but this one holds special significance for general manager Jeremy O'Day, who has now experienced championship glory from both sides of the game.
From Player to Executive: A 26-Year Journey
Jeremy O'Day recently completed his 26th consecutive year with the Saskatchewan Roughriders, a milestone that even surprised long-time observers of the Canadian Football League. The 51-year-old executive just secured his first CFL championship as a general manager when the Roughriders defeated the Montreal Alouettes 25-17 in the 2025 Grey Cup.
O'Day described the emotional victory as feeling "like a proud father" while watching his team celebrate. This championship adds to his already impressive resume with the community-owned franchise, having previously won Grey Cups as a player in 2007 and as an assistant general manager in 2013.
Different Roles, Same Championship Feeling
The veteran football executive compared his championship experiences, noting both similarities and differences between winning as a player versus as an executive. "When you win as a player you can maybe drink a little bit more champagne and celebrate with your teammates a little bit more," O'Day recalled during his season-ending media availability.
He explained that as general manager, his post-victory focus shifted toward congratulating players and connecting with their families at the post-game celebration. "Certainly the same feeling; I wouldn't say it's much different when you win. You're elated for guys that have fought so hard through the season, you see those guys breaking down with their parents. That's a pretty special moment," O'Day emphasized.
Building a Championship Roster
O'Day's fingerprints are all over the current Roughriders roster. With assistance from Paul Jones, Kyle Carson, Larry Dean, and Jordan Greenly, the general manager has drafted, signed, or re-signed every player on the championship team. This comprehensive team-building approach culminated in the franchise's first Grey Cup victory since 2013.
The 2025 championship marks a significant milestone in O'Day's transition from player to executive. His journey with the Roughriders began in 1999 when he left the Toronto Argonauts after two seasons that included a Grey Cup victory in his rookie campaign against Saskatchewan.
O'Day joined the Roughriders as a free agent, telling reporters at the time that he wanted to become a full-time starter on Saskatchewan's offensive line. The American from northern New York with Canadian-born parents—making him a "non-import" player—believed his opportunity was better in Saskatchewan, where the team was struggling through eight straight sub-.500 seasons under four different head coaches.
During his playing days, O'Day became a team captain and was regularly called upon to defend his teammates. Media members recall him as always available for one-on-one interviews in the pre- and post-practice sessions that characterized a different media era in sports coverage.
What makes O'Day's longevity particularly remarkable is that he never expressed interest in becoming an administrator during his playing career. He negotiated his own contracts as a player and, according to those who covered the team closely, never mentioned aspirations for front-office work.
Yet his 26-year tenure with the Roughriders has now come full circle, with O'Day helping to deliver another championship to Saskatchewan fans and cementing his legacy as one of the franchise's most important figures across multiple eras of CFL football.
