Oak Park grads Oliveira and Demski cheering on Raiders
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Hey there, time traveller!
This article was published 06/11/2024 (334 days ago), so information in it may no longer be current.
The West Division Final isn’t the only big game that’s pulling Brady Oliveira to Princess Auto Stadium this week.
The Winnipeg Blue Bombers running back will be in attendance supporting his former high school, the Oak Park Raiders, in the Winnipeg High School Football League AAAA championship game against the Dakota Lancers on Thursday (7:30 p.m.).
“I’m gonna try and swing by here and catch the game,” Oliveira said Wednesday. “Obviously, a big game for the Raiders and hopefully another championship for the legacy of that great program. Two big games coming up at Princess Auto Stadium.”

Tara Walton / THE CANADIAN PRESS files
Brady Oliveira
Oliveira spent the 2012 and 2014 seasons at Oak Park where he made a name for himself as one of the best young players in the province. He was named WHSFL Rookie of the Year in his first year with the Raiders, then, after returning from Canada Prep Academy in Ontario, tore up the record books in his Grade 12 season, rushing 170 times for 2,220 yards and 34 touchdowns, and adding six catches for 142 yards and two majors.
His record-breaking year culminated in a provincial championship, which the Raiders won at the stadium. Oliveira maintained it’s an experience no player will ever forget.
“I’m in my fifth year pro and I always will remember that game,” he said. “Word of advice for the kids playing tomorrow: enjoy and embrace every single moment because I promise you 10 years, 15 years down the road, you’ll always remember that game.”
Nic Demski, another Oak Park alum on the Bombers, won’t be in attendance Thursday but said he will be cheering from home.
Demski rose to prominence in his Grade 11 and 12 seasons after switching from quarterback to running back and receiver. He helped lead the Raiders to a provincial championship in 2010, his graduating year, when he was named Most Valuable Player and the league’s Offensive Player of the Year.
The Bombers receiver offered his own words of encouragement to this year’s group:
“I played in two championship games there for Oak Park — one of them we won, one of them we lost — so all I’d say is keep calm, cool and collected, man,” he said. “At the end of the day, obviously you’re going to know the magnitude of the game, it’s a championship game, but it’s just another opportunity to go out there and play with your teammates and have fun.
“As long as they do the right things and play for each other, good things will always happen.”

MIKE DEAL / FREE PRESS files
Nic Demski
Both Demski and Oliveira stay in touch with members of the Raiders football program. Oliveira said he supports the team in any way he can, including past visits to the locker room to speak with players. Demski has taken a more hands-on approach with some players through the Recruit Ready development program during the off-season.
Both said they have kept tabs on this year’s team, which, along with Dakota, has been the most dominant squad in the high school loop, recording 346 points for to zero points against during the seven-game regular season.
“There were great teams in the past with Oak Park. Nic was on some pretty good teams, I was on some pretty good teams, but it seems like this is the team of the century for the Oak Park Raiders,” Oliveira said. “It really looks like they have everyone on that team so hopefully they can cap it off with a victory (Thursday) night and get a championship.”
joshua.frey-sam@freepress.mb.ca
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Josh Frey-Sam reports on sports and business at the Free Press. Josh got his start at the paper in 2022, just weeks after graduating from the Creative Communications program at Red River College. He reports primarily on amateur teams and athletes in sports. Read more about Josh.
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