The year 2024 will be replete with milestones for Jeremy O’Day.
Feb. 26: O’Day, now the Saskatchewan Roughriders’ Vice-President of Football Operations and General Manager, will mark 25 years since he joined the CFL team — as a free-agent signing in 1999.
May 1: O’Day and his Regina-born wife, Dana, will celebrate their 20th wedding anniversary.
Aug. 31: Precisely 50 years will have elapsed since O’Day was born in Lockport, N.Y.
“What’s pretty crazy is that when I hit 25 years, I’ll have been a Roughrider for more than half my life,” O’Day reflects.
Which brings us to one more milestone: On Jan. 18, he will reach the five-year mark as the Roughriders’ GM. That will be his 1,836th day in office.
As it stands, O’Day is the fifth-longest-serving Roughriders GM since 1954, when Dean Griffing became the first person in franchise history to hold that position on a full-time basis.
Griffing (1,365 days) is sixth on the team’s all-time GMs’ longevity list, behind Ken Preston (7,184), Alan Ford (4,014), Roy Shivers (2,433), Brendan Taman (2,048) and O’Day, who will reach yet another milestone — 2,000 days as the GM — on June 30.
None of this was even remotely imaginable on a winter’s day in 1999, when O’Day signed with Saskatchewan after spending his first two CFL seasons in Toronto with the Argonauts.
“When I became a Roughrider, there’s two things that I remember,” O’Day reflects.
“One was my mom telling me not to go find a girl in Saskatchewan, because she was worried that I’d be too far away. I didn’t listen to her on that one.
“The other one is that I remember counting up all my leftover change and convincing one of my best friends from high school, Justin Kwoka, to drive here with me. I promised to fly him back, so I actually flew him back with all the change that I had counted.”
Talk about a change of scenery!
“He agreed to do it,” O’Day continues, “and we actually drove through Canada when we came up from (the Buffalo area). It’s a little bit longer than going through the States.
“There were winding roads and lots of evergreens.”
O’Day has been green ever since, even though his introduction to Saskatchewan was not the smoothest.
Neither was the tattered, patchwork artificial turf at Taylor Field when O’Day arrived in Regina.
The uneven, abrasive playing surface had been installed more than a decade earlier and was far beyond its best-before date.
Making matters worse, the 1999 Roughriders posted a 3-15 record.
All the same, the move to Saskatchewan opened new doors for O’Day, who quickly developed a love for this area of the world.
By the early 2000s, he was entrenched as a starter on an offensive line that would become one of the CFL’s finest.
He found a home in Regina — and at centre for the Roughriders.
Six times a West Division All-Star, he was named an All-Canadian in 2006, 2007 and 2009.
In 2007, he helped Saskatchewan secure its first home playoff game in 19 years and win the third Grey Cup championship in franchise history. (He had previously won a title in 1997, as a rookie with the Doug Flutie-quarterbacked Argonauts.)
During Grey Cup week in 2008, O’Day received the prestigious Tom Pate Memorial Award, which recognizes exemplary conduct and contributions on and off the field.
Then came 2009, when the Roughriders earned first place in the West Division for the first time since 1976.
When the team next ascended to top spot, in 2019, O’Day was the Roughriders’ GM/Vice-President of Football Operations.
He made a seamless transition into football operations upon announcing his retirement as a player on Feb. 8, 2011, only a few months after being named an All-Star once more.
Despite the surprising retirement announcement, he wouldn’t spend a millisecond outside of the Roughriders’ organization. He made an immediate, seamless transition into the role of Football Operations Co-ordinator.
Nine months later, O’Day was promoted to Assistant GM and retained that title through the midpoint of the 2015 CFL season.
Along the way, he earned a second Grey Cup ring — helping to build a 2013 Roughriders team that posted a landmark home-field championship-game victory.
By then, it was essentially a hometown victory for the American-born O’Day.
Such is the degree to which the O’Day family has become entrenched in the community.
Jeremy and Dana’s first child, Tyson, is now 19 and in his second year at the University of Regina. He is also a receiver with the Prairie Football Conference’s Regina Thunder.
Brooklyn, 17, is in Grade 12 at Martin Academy. A member of the Regina Diving Club, she has accepted an athletic scholarship from the University of Alabama.
Alyssa, 16, is in Grade 11 at Winston Knoll Collegiate, where she excels academically and in extracurricular activities such as school musicals.
“I feel like we were just teaching them how to tie their shoes,” a proud father marvels, “but now they’re driving cars and picking what they’re going to do in school.”
Meanwhile, their father is in the business of picking players, along with performing the sundry duties that are part of a General Manager’s purview.
O’Day is actually well into his second stint in the GM’s chair.
After a front-office shakeup on Aug. 31, 2015, O’Day was named the interim GM.
When Chris Jones was hired as the Head Coach, General Manager and Vice-President of Football Operations in December of that year, O’Day remained on-board in the new role of Assistant Vice-President of Football Operations and Administration.
After serving in that capacity for three-plus years, O’Day assumed his current role shortly after Jones’s departure for the NFL’s Cleveland Browns in January of 2019.
Nearly five years later, a milestone-filled 2024 is nigh for O’Day.
Twenty-five years as a Roughrider … right around the corner.
“It’s pretty special,” he reflects. “Every once in a while, I think back to when I first got here and about how much it has changed — how the organization has changed as a whole.
“The fan base has been consistent the whole time I have been here, but for the organization — from the business office to the stadium that we’re in now — the changes that we’ve gone through have been pretty amazing.
“It feels like it was a long time ago but, by the same token, it doesn’t feel like it was a long time ago.
“I actually remember the first day I pulled in behind the old Taylor Field. I looked at it and thought, ‘Where am I and what am I doing here?’
“But, even back then, it didn’t really matter. The people, the fans, the focus on football, and how important it is for people was the big deal that kind of sucked me in.
“It didn’t hurt that I met my wife here and I started my family here.
“I like the smaller cities. It’s nice when your phone says that you’re a whopping 12 minutes from home — on a bad day.
“I came from a (CFL) team where you could go wherever you wanted and nobody really knew who you were.
“Here, the people know you are, but that’s not the important thing. People just want to talk to you about the Roughriders.
“Here, it’s still cool to wear jerseys to games. It’s cool to put green and white on and get dressed up.
“Game days are a tradition. It’s not just about going to a game. It’s a whole process for the people of Saskatchewan.”
That description has long applied to O’Day, despite his ties to western New York state.
“Because I’ve been here for so long, I’ve seen people grow up as Rider fans, from when they were little to when they become older,” he continues.
“When we won a Grey Cup, there were people showing up to get pictures of the Grey Cup, and they have their old picture from the last time we won, when they were babies or they had a young family.
“They’d bring in their old picture to get a new picture. That’s what I’m looking forward to the most — to having that again.
“In my house, there’s the last Grey Cup picture, and the kids are too small. We’re due to get back and win a Grey Cup.”
