Jeremy O’Day is poised to celebrate two diamond anniversaries.
The Saskatchewan Roughriders’ Vice-President of Football Operations and General Manager excitedly awaits the 60th Labour Day Classic — today’s matchup with the Winnipeg Blue Bombers (5 p.m., Mosaic Stadium).
A few hours after starting at centre for Saskatchewan in the 39th such game, played 22 years ago today, O’Day offered a sparkling engagement ring to his future wife, Dana.
“I always tell everyone, ‘I lost the game, but I’ve been winning ever since,’ ” says a smiling O’Day, the proud father of Tyson, Brooklyn and Alyssa.
The original (and ultimately successful) plan was for O’Day to propose on his birthday — which was then his 29th. However, the Blue Bombers’ 36-18 victory led him to ponder a deferral.
“We lost the game, so I wasn’t going to ask her that day,” he recalls.
“(Fellow offensive lineman) Rob Lazeo noticed that I was a little more dejected than normal after a loss. He asked, ‘What’s going on?’ He actually sat me down.
“I said, ‘I was going to ask Dana to marry me today. He said, ‘If you’re going to do it, you need to do it. It’s just another game.’ ”
Another factor to consider: The cat was already out of the bag, so to speak.
In an old-school move, O’Day had sought out Dana’s father (Don Steidl) the previous day to formally request permission to marry his daughter. Permission was granted, but the news was kept from O’Day’s future mother-in-law, Marge.
O’Day took everything into consideration and followed through on the proposal, which was quickly accepted.
“I asked her and then we went right to her parents’ house,” he says. “We walked on to the deck and everyone was sitting there.
“Her dad saw us coming and went into the house. Dana walked up to her mom and just put her hand out. Her mom saw it and started jumping up and down. Then Don walked out with champagne. He was already ready for a toast.
“My mother-in-law looked at him immediately and said, ‘You knew?!’ He said, ‘Yup!’ ”
More good news: The Labour Day weekend loss was avenged 63 days later when the Roughriders posted a 37-21 playoff victory in Winnipeg.
When the Roughriders and Blue Bombers next met in the post-season, Saskatchewan registered a 23-19 Grey Cup victory on Nov. 25, 2007.
A sellout crowd of 28,800 was treated to a championship-game preview on Sept. 2 of that year, when the Roughriders won 31-26 in what is widely regarded as the best of all Labour Day Classics.
With six seconds remaining, Kerry Joseph scored the game-winning touchdown on a 27-yard quarterback draw. O’Day made one of the key blocks, driving a Bombers defensive lineman to the north as Joseph began his southward sprint to the end zone.
“For me, the best one — the funnest one — was ’07,” O’Day says.
“Kerry got skinny and got through the hole. They were blitzing on the play, so there was no second level and no contain. He ran in for the big score.
“That was a big one and it was exciting.”
A quarterback had also made headlines five years earlier, when Rocky Butler made a surprise start behind centre and piloted the Roughriders to a 33-19 upset victory over Winnipeg.
O’Day had an unaccustomed vantage point on Sept. 1, 2002. He watched from Taylor Field’s west sideline.
He suited up for all 18 regular-season games in 10 of his 13 years as a Roughriders player. One of the exceptions was the 2003 season, in which he missed five games after suffering a torn ligament in his right knee.
Andrew Moore started at centre as Butler, who got the nod at quarterback due to the Roughriders’ rash of injuries at that position, ran for three touchdowns.
“He was our fourth-string quarterback coming into camp, so it was the first game he played,” O’Day remembers. “I remember on the one run he scored on, his helmet got knocked off.”
The headgear went flying as Butler landed in the north end zone to complete a 32-yard touchdown run on a quarterback draw — the same play on which Joseph took off five years later.
All these years later, O’Day awaits his 26th Labour Day Classic.
Today’s contest will even his personal slate: 13 Classics as a player and as a key member of the football-operations staff.
As it stands, the Roughriders are 18-7 in Classics since he joined the team in 1999.
Saskatchewan was victorious in his first Classic as a player (42-25 in 1999), a member of the front office (27-7 in 2011), an interim GM (37-18 in 2015) and the full-time GM (19-17 in 2019).
The latter game ended in unforgettable fashion when Brett Lauther kicked a 26-yard field goal to give the Roughriders a 19-17 win.
“After Brett’s walk-off in 2019, I remember him and (holder) Jon Ryan jumping into Pil Country,” O’Day says.
Long before Pil Country, the territory behind the south end zone at the Roughriders’ home facility was unofficially known as Hemorrhoid Hill. There wasn’t any formal seating, but the area was a popular destination for overflow customers — including resourceful Rider Priders who brought lawn chairs.
“To me, it goes back to the old stadium where there was grass in the end zone and it was standing room only,” O’Day reflects. “You got excited because you knew it was going to be the biggest crowd of the year.
“If people came back for one game, it was always the Labour Day game.”
A contest that often leaves the fans — and, in one case, the starting centre — engaged.