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Winnipeg Blue Bombers star running back Brady Oliveira is in the midst of a 1,000-yard season.James Carey Lauder/USA TODAY Sports via Reuters

Sunday’s 109th Grey Cup game will feature three players who all walked the halls of the same Winnipeg high school, each starring in different years for its popular football team, the Oak Park Raiders.

Andrew Harris, Nic Demski and Brady Oliveira each had their own unique electrifying seasons for the Raiders in the Winnipeg High School Football League and remain a source of pride for the school today.

Cheering for the trio in this Grey Cup creates mixed feelings for their old high school coaches, though. While Demski and Oliveira aim to help their hometown Winnipeg Blue Bombers win their third successive CFL’s championship game, Harris is suiting up for the opposing Toronto Argonauts after five seasons and two Cups with the Bombers.

“I grew up in Winnipeg, so I cheer for the Bombers,” said Stu Nixon, who coached all three players at Oak Park High School. “The best way we could spread this out would be for Andrew to get 150 yards and a touchdown, and maybe 80 yards in receptions, and be the Canadian player of the game, and then the other two guys get the championship.”

Nixon, recently retired, will drive to Regina from Winnipeg to attend Sunday’s Grey Cup. Some other Oak Park coaches will watch together at a Winnipeg sports bar. This isn’t the first time this trio of Oak Park players are in the country’s most famous annual football game.

They won the past two Grey Cups together as Blue Bombers – with the veteran running back Harris the game’s most-outstanding Canadian and MVP in 2019; then slotback Demski the top Canadian in the 2021 game. Oliveira was on the injured list in 2019, a young backup, mentoring under Harris through 2021.

Going into 2022, and approaching age 35, Harris said he there was a lack of communication from the Bombers about a new contract and he felt unwanted. So he signed with the Argos. Now 25-year-old Oliveira is Winnipeg’s star running back, in the midst of a 1,000-yard season. This Grey Cup will pit them as foes.

“Andrew and Brady have very similar styles; it’s going to be neat to see both of them compete in really tough weather conditions,” Nixon said.

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Toronto Argonauts running back Andrew Harris spent five seasons and won two Grey Cups with the Winnipeg Blue Bombers.Heywood Yu/The Canadian Press

Harris was a high school kid in the early 2000s, so he was the first of this trio to star at Oak Park – a school of some 900 students where about 90 play for its varsity and junior varsity football teams, which routinely draw hearty crowds to their games. They’ve had a handful of players drafted to the CFL.

Harris transferred to Oak Park for his senior season (2005), after his concerned football coach at another school, Grant Park, called Oak Park and said, as Nixon recalls, “‘you got to get him out of this school. He’s hanging out with the wrong people and making the wrong decisions.’ That coach was giving up his best player because he knew he had to help the kid.”

Nixon had known Harris from coaching at Grant Park a few years earlier. On top of football, Harris was a stellar hockey player, too, and dazzled at pickup basketball, but he and his mother moved around a lot, and he lacked a father figure. He turned that negative energy into fierce fuel as a game-breaking running back, who also returned punts and kicks.

“Andrew was guarded with his emotions, but off-the-charts athletic,” Nixon said.

With Harris as its star, that Oak Park team made it to the championship game. He didn’t head off to play in university, though. Harris made it to the CFL via a very rare path – through junior football. Thriving with the Vancouver Island Raiders with people who treated him like family, he landed a spot with the CFL’s B.C. Lions in 2009. There he won a Grey Cup in 2011 and started a standout pro career that is likely to land him in the Canadian Football Hall of Fame.

The next standout teen in Oak Park High School’s backfield was Demski in the late 2000s. The coaches recalled seeing Demski as an eight-year-old at one of their youth camps several years earlier – already sporting a unique burst of speed, and a sense of when to cut or hit the hole straight ahead. They eagerly awaited his arrival in high school.

Demski, who today is 28, shone back then at hockey and soccer, too. Multitalented on the football field, he could run or play quarterback.

“In high-school football, you want to get the ball to your best player, right?” says Steve Ollson, long-time assistant coach who recently took over Oak Park’s football program after Nixon’s retirement. “So get it to Nic. He’s got an ability to see the field and make special plays, to just make people look silly out there.”

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Winnipeg Blue Bombers receiver Nic Demski won a championship with Oak Park High School in his senior year.John Woods/The Canadian Press

In Demski’s senior season, 2011, Oak Park won a championship.

“Nic, the dude was high on life. He was just filled with joy, one of the happiest kids you’ve ever met,” Nixon said. “He’d walk into a room or a gymnasium and you could feel the electricity off him, just got some really solid positive karma.”

A few years later, Oliveira was the next star rusher at Oak Park. He had turned heads as a 10th grader, called up to the varsity team, then left briefly for Grade 11 to attend a specialty football prep school in St. Catherine’s Ont. He returned to Oak Park for Grade 12, where they won a championship in 2015.

“Brady was that ground-and-pound kind, put his head down and get the hard few yards,” Ollson recalls. “Even as a Grade 10 kid, he was just running through everybody, didn’t matter how big they were. He was just playing at a different level. He worked and worked at it. He looked like a grown man in high school.”

Today Oliveira’s name is still all over the Winnipeg High School Football League records in Class AAA & AA for rushing yards, points and touchdowns. Some of the records he eclipsed were Demski’s.

Oliveira went on to play at the University of North Dakota before the Bombers drafted him in 2019.

“Brady, Nic and Andrew, they never played together in high school, but when they eventually all got to the Bombers, I think Andrew was like an older brother to them,” Nixon said.

All three have remained in touch with the high school. The school held pep rallies before Grey Cups in the past, the gym and its students decked in blue, white and gold, with large cardboard cutouts of the three players bouncing among the crowd. Demski and Oliveira brought the Grey Cup for a visit with students last spring. The three CFLers have contributed to youth football programs and fundraisers and provided some mentorship to Raider high school players.

“We just feel incredibly lucky,” Ollson said, “to have had all of those guys in our program.”

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