A rookie and a ’Vette: Riders GM Jeremy O’Day reflects on introduction to CFL

WINNIPEG — Fittingly, Jeremy O’Day’s first Grey Cup involved the Saskatchewan Roughriders.

He was a member of the opposition in 1997, when the Toronto Argonauts faced the Green and White at Commonwealth Stadium in Edmonton.

“I would have been a rookie and there was no attention, which was fine,” the Saskatchewan Roughriders’ Vice-President of Football Operations and General Manager recalls leading up to Sunday’s CFL championship clash with the Montreal Alouettes at Princess Auto Stadium.

“We had Doug Flutie and Mike Vanderjagt and Pinball Clemons and Derrell Mitchell, so there was plenty of them to choose from and I was a part-time starter.

“I think my biggest decision of the week was what kind of shoes to wear on game day. We ended up wearing broomball shoes, because it was frozen.

“It was obviously a great experience. To be able to do that in your first year, it was pretty awesome.”

That was the first of three championship seasons for O’Day, who signed with Saskatchewan as a free agent in 1999 and subsequently earned Grey Cup rings as the Roughriders’ starting centre (2007) and the Assistant GM (2013).

Now he is at the Grey Cup Festival for the first time as a competing team’s GM, having assembled a squad that finished with the CFL’s best record (12-6) in 2025.

“I’d be lying if there wasn’t a sense of pride, knowing that you had a part in putting the team and the staff together and seeing where it has come,” he says.

“There are my experiences of being in Saskatchewan through good times and tough times. I think that all factors into the emotions that go into this week.

“I try not to get too emotional about it and try to focus on helping everyone through the week and making sure that everyone is prepared and has everything that they need to be successful in the game.”

O’Day tasted success right away after proceeding to the CFL from Pennsylvania-based Edinboro University — also the alma mater of Roughriders quarterback Trevor Harris.

The Argonauts, with Flutie in the eighth and final season of a spectacular stay in Canada, finished 15-3.

One of the early-career highlights for O’Day took place in the very city where he hopes to celebrate a championship on Sunday.

On Sept. 7, 1997 against the host Winnipeg Blue Bombers, O’Day lined up as an eligible receiver and caught a touchdown pass from Flutie in a 66-25 Argonauts rout.

That was one of 47 TD passes thrown by Flutie in 1997, when he was named the CFL’s Most Outstanding Player for an unprecedented sixth time. What a show that was.

“It was awesome for me,” O’Day says. “He lived in the same building. He was a fun guy.

“We used to play Sega hockey against each other all the time. He was a super-competitive guy. And if you beat him, he just wanted you to keep playing him all the time.

“I don’t know if he was that great and he probably doesn’t remember, but he was good at almost everything — but he wasn’t great at that.

“I was making $28,000 a year and he was the highest-paid player in the league. I remember after an away game, he asked me if I could go back to the airport because he left one of his cars there. He had a Porsche and a Corvette.

“We got there and he said, ‘Which one do you want to drive?’ I said, ‘Which one is the cheaper of the two?’ That’s the one I drove back.”

(It was the Corvette, by the way.)

“He had a Corvette and a Porsche and I was making $28,000 Canadian, blocking for him,” O’Day continues. “But he was just great. He was fantastic.

“He’s one of the most prepared and competitive guys — a guy who will go under a door and jump up and see how high he can touch.

“He spent endless hours preparing. It was awesome to play with him. I think I was too young to realize it at the time but certainly, as time has passed, I realize just how impressive he was as a player.

“We’d go out and he’d be 12-for-12 in skelly. You just thought it was normal, but it was not.”

O’Day played a second season in Toronto before signing with Saskatchewan on Feb. 26, 1999.

As a first-year Roughrider, he caught a second touchdown pass — a seven-yarder from current University of Texas Longhorns head coach Steve Sarkisian against the host B.C. Lions on Nov. 5, 1999.

“I played against a lot of (members of the 1999 Roughriders) in the Grey Cup in ’97 and now I’m their teammate in ’99, so we had that memory,” O’Day reflects. “It was interesting to hear their perspectives compared to our perspective.

“To be honest, it took us a while in Saskatchewan to get back to the Grey Cup after I got here. It was a slow climb, but we eventually got there and had a chance to play for it in ’07, ’09, ’10 and ’13.”

Along the way, O’Day earned three All-CFL nominations and was a six-time divisional honouree.

He retired at the top of his game, having been named the Roughriders’ Most Outstanding Offensive Lineman in 2010. He had previously received that award in 2001, 2006 and 2007.

In the latter season, O’Day and fellow offensive lineman Gene Makowsky were the first Roughriders players to touch the Grey Cup following a 23-19 victory over the Blue Bombers at Toronto’s SkyDome (now the Rogers Centre).

At the very same venue, O’Day had made his CFL regular-season debut on June 27, 1997. Toronto defeated Winnipeg, 38-23.

The once-upon-a-time SkyDome was also the site of Flutie’s first Grey Cup celebration, after he had quarterbacked the Calgary Stampeders to a 24-10 win on Nov. 29, 1992. The opponent: Winnipeg.