The Saskatchewan Roughriders have never repeated as Grey Cup champions and general manager Jeremy O’Day hopes the chance to go back-to-back might help pending free agents stay with the Green and White.

“Not to get too far ahead of ourselves, but there’s already a lot of talk about being the first team to repeat. I think that every team that wins says the same thing, but it’s never been done here before,” O’Day said. “There’s a little bit of added motivation there to our players; being the first team to do it here would be special.”

The Riders won the franchise’s fifth Grey Cup championship when Saskatchewan defeated the Montreal Alouettes 25-17. The Roughriders captured the CFL championship in 1966, 1989, 2007 and 2013 to go along with 2025. 

“After we knocked down that last pass, I don’t want to say I blacked out, but it was chaos,” O’Day recalled. “We wanted to get down on the field as soon as possible because we were upstairs, you realize that the season’s over, but you realize that you won the championship. It’s elation, it’s excitement, a little bit of relief, lots of happiness.” 

O’Day explained what happened after the Grey Cup and the balancing act of enjoying the moment and still working.

“There’s some celebration that everyone is well aware of. I think it’s important, these guys work so hard in what they do, to get the opportunity to celebrate a championship that doesn’t come around very often” O’Day said.

“Then you have the parade, the next day hits, you’re having exit meetings with the players, and their contracts are up. You’re trying to give them the information that you can and make sure they understand we want them to be back. Now we’re a week out, and we’re already back at it, so it flips pretty quickly. The coaches need some well-deserved time off, but for us in football ops, we got to keep working.”

Historically for O’Day, it was his fourth Grey Cup win after winning his first two as a player: in 1997 with the Toronto Argonauts and 2007 with the Riders. The next one came in 2013 as an assistant general manager with Saskatchewan.

The Roughriders have 45 pending free agents, according to 3DownNation insider Justin Dunk. O’Day knows his staff will have their work cut out for them.

“Ultimately, it’s going to come down to how many of them we’re able to get back. It’s going to be difficult to bring every one of the receivers back because we have a salary cap. I also say, two years ago, those guys weren’t on our team. We have a responsibility as well to replace players. If one of our players goes to another team because they have a better financial opportunity, that’s out of our control,” O’Day explained.

“The cap is what it is. When we look at the roster as a whole, we’re going to try to put the best roster available, not the best couple of players. We’ll face some challenges, as we do every year. Yes, there’s a lot of guys that are free agents, but it happens that way every year. We know what we’re doing.”