Precisely 18 years after Jeremy O’Day first celebrated a Grey Cup title as a Saskatchewan Roughrider, he met with reporters to summarize the fifth championship season in franchise history.
O’Day has been a part of three of those Cup-winning efforts — as a centre (2007), Assistant General Manager (2013) and, now, as the Vice-President of Football Operations and General Manager.
The Roughriders captured their most-recent title on Nov. 16, defeating the Montreal Alouettes 25-17 at Princess Auto Stadium in Winnipeg.
Saskatchewan’s 2024 season also concluded in the Manitoba capital, where the Winnipeg Blue Bombers won last year’s Western Final and advanced to the Grey Cup for the fifth season in succession.
“We talked about it last year after we lost in Winnipeg that it was very important for us to get first place and to get a home playoff game,” O’Day said on Tuesday.
“You can see the difference that made. Having a home game for the Western Final was a big deal.”
Especially when the Roughriders defeated the B.C. Lions 24-21 on Nov. 8 at Mosaic Stadium to advance to the 112th Grey Cup Game.
With green and white confetti flying, Roughriders quarterback Trevor Harris was named the 2025 Grey Cup’s Most Valuable Player after completing 23 of 27 passes for 302 yards and directing three touchdown drives. His completion percentage (85.2) set a Grey Cup record.
Most Valuable Canadian honours went to Samuel Emilus after his 10-catch, 108-yard performance. Emilus was chosen by O’Day in the first round (seventh overall) of the 2022 CFL Draft. The Roughriders’ GM signed Harris as a free agent the following year.
Player retention is one of the critical factors as the Roughriders set their sights on being a repeat champion.
Harris, who is on an expiring one-year contract, told reporters last week he would be “shocked” if he did not return to the field in 2026.
However, the 39-year-old signal-caller also emphasized that he would take time to discuss the decision with his family before making any definitive announcements. He doesn’t expect it to be a protracted process.
“No breaking news today,” O’Day said with a chuckle on Tuesday. “We’ve had discussions. Trevor got on the road a couple of days ago and we had a good discussion before he left.
“Right now, it’s an early conversation. We’d love to have Trevor back and I think he knows that. It’s just a matter of us getting back on the phone and trying to work something out.”
The Montreal-born Emilus, a two-time 1,000-yard receiver, signed a new contract in April of 2024 that extended through the 2025 season. He is among many Roughriders receivers who can test free agency in February if agreement on a new contract is not reached beforehand.
“It’s a group that’s loaded with really good players,” O’Day said. “Ultimately, it’s going to come down to how many of them we’re going to be able to get back.
“It’s going to be difficult to bring every one of the receivers back, just because we have a salary cap. But I also say that two years ago, (some of) those guys weren’t on our team.
“We have a responsibility as well to replace players. If one of those players goes to another team because they have a better financial opportunity, that’s kind of out of our control. The cap is kind of what it is.
“When we look at the roster as a whole, we’re going to try to put together the best roster available, not just the best couple of players.
“We’ll have some challenges like we do every year. Yes, there’s a lot of guys who are free agents, but it kind of happens that way every year.”
O’Day has been a Roughrider every year since 1999, when he signed with the team as a free agent. He retired as a player in February of 2011 — despite coming off a season in which he was a divisional All-CFL selection for the sixth time — and soon moved into football operations. He has headed that department on a full-time basis since Jan. 18, 2019.
With O’Day in the GM’s chair, Saskatchewan has twice finished first in the West Division (2019, 2025), appeared in four Western Finals (2019, 2021, 2024, 2025) and won one championship.
As one who settled in Regina and raised his family here, he has an advanced understanding of what a Grey Cup win means for Rider Nation and the team’s bottom line.
“I hope it’s good for business,” O’Day said, adding that the fan support in 2025 was “awesome,” as was last week’s Grey Cup parade.
“With players, it just helps when you’re coming off a championship. Not to get too far ahead of ourselves, but I think there’s already a lot of talk about being the first team to repeat.
“I think that every team that wins it says the same thing, but it has never been done here before, so there’s a little bit of added motivation for our players. Being the first team to do it here would be special.”