The Birth of a Gridiron Tradition: The Oak Park Raiders (1991-2001)
While École Secondaire Oak Park High School had been a pillar of the Charleswood community in Winnipeg since the mid-1970s, its celebrated football story began in 1991. [1] That year, the school officially established the Oak Park Raiders football program, entering the highly competitive fray of the Winnipeg High School Football League (WHSFL). The WHSFL was a league with a deep and storied history, and the new Raiders team, clad in their signature blue, white, and silver, faced the daunting task of carving out their own identity among established powerhouses.
The early years of the program were foundational. Like any new team, the Raiders experienced the growing pains of building a culture, developing players, and establishing rivalries. This period was crucial for laying the groundwork for what would become one of Canada’s most respected high school football dynasties. Coaches and players in the 1990s worked to instill a sense of discipline, resilience, and pride in the Raiders jersey. They battled on the field, steadily building a reputation for toughness and beginning the long process of climbing the WHSFL ranks. While detailed records from this initial decade are sparse, the effort and dedication of these early teams were the bedrock upon which a legacy of excellence would be built. They were the pioneers who set the stage for the golden era that was to follow.
The Golden Era: The Stu Nixon Dynasty (2002-2022)
The trajectory of the Oak Park Raiders football program changed forever with the arrival and influence of Stu Nixon. Though he joined as an assistant coach before taking the helm, his name became synonymous with Oak Park football for over two decades. [2][3] Nixon, who retired in 2022 after a 35-year teaching career, with the final 20 years spent at Oak Park, was more than a coach; he was an architect of success and a mentor to hundreds of young men. [3][4] His passing in May 2025 was mourned by the entire community, a testament to the profound impact he had on his players’ lives. [4]
Nixon’s coaching philosophy extended far beyond the Xs and Os of the game. He was remembered by his players, including CFL star Brady Oliveira, as a “father figure” who provided guidance and support both on and off the field. [4] This holistic approach to coaching—focusing on developing character as much as athletic skill—created a culture of accountability and excellence that produced staggering results.
Under Nixon’s leadership, the Raiders became a perennial powerhouse in the WHSFL. His remarkable list of accomplishments includes leading the team to numerous provincial championships and finals. He was an assistant coach on the 2002 championship team and, as head coach, guided the varsity team to ANAVETS Bowl (the WHSFL’s top-tier championship) victories in 2007, 2010, and 2014, along with finalist appearances in 2004, 2009, and 2011. [2][5] He also found success at the junior varsity level, coaching that team to a championship in 2017. [6][7] In recognition of his incredible career and contributions to the sport, Stu Nixon was posthumously inducted into the Manitoba Football Hall of Fame in 2023. [2][4]
The success during the Nixon era was a team effort, a fact Nixon himself was quick to point out. He credited a long-standing and dedicated coaching staff, including names like Ryan Soroka, Dave Black, and Chris Ollson, who were instrumental throughout the journey. [5] This stability in leadership ensured that the program’s values and high standards were consistently passed down to each new class of players.
The CFL Factory: A Legacy of Professional Talent
Arguably the most defining feature of the Oak Park Raiders program is its unparalleled success in developing elite football talent. The school has earned the reputation of being a “veritable assembly line of CFL talent,” having produced more professional football players than any other high school in Canada. [5][8] This extraordinary legacy is a direct result of the high-performance culture and expert player development fostered under Coach Nixon. The list of alumni who have gone on to star in the Canadian Football League is a who’s who of Canadian talent.
Andrew Harris: A true legend of Canadian football, Harris led the Raiders to the championship final in 2004. [9] His professional career saw him become one of the most dominant running backs in CFL history, winning multiple Grey Cups and a Grey Cup MVP award. [9][10]
Nic Demski: A key member of the 2010 Raiders championship team, Demski has become a versatile and explosive offensive weapon for his hometown Winnipeg Blue Bombers. [9][11] He has explicitly credited Coach Nixon and his time at Oak Park for preparing him for the rigors of a professional career. [8]
Brady Oliveira: Oliveira captained the Raiders to a championship in 2015 and has since emerged as one of the CFL’s premier running backs, also with the Blue Bombers. [9][11] He has been named the CFL’s Most Outstanding Canadian twice. Oliveira’s deep personal connection with Nixon highlights the coach’s profound influence beyond the football field. [4][11]
Sean Jamieson: Another product of the Raiders’ system, Jamieson has forged a successful career as a professional offensive lineman, notably with the Montreal Alouettes. [2][11]
Charlie Ringland: A gifted multi-sport athlete, Ringland was a standout for the Raiders. He served as a two-way starter, playing quarterback and free safety. [12] In his senior year, he cemented his place in Raiders history by throwing for three touchdowns to lead the team to the 2017 WHSFL CTV Cup championship. [7][12] After a stellar university career with the Saskatchewan Huskies, where he was named a Canada West All-Star, Ringland was drafted into the CFL in 2023. [12][13] His journey reflects the program’s continued ability to produce top-tier talent, having been coached in the offseason by fellow alumnus Nic Demski and having shared a high school hallway with Brady Oliveira for a year. [14]
The success of these alumni has brought national acclaim to the program. Their continued involvement, often giving back to the team and mentoring current players, strengthens the powerful sense of community and tradition that defines Oak Park football. [8]
A Tradition of Excellence Continues (2022-Present)
The end of the Stu Nixon era did not signify an end to the Raiders’ dominance. The torch was passed to Chris Ollson, a man deeply embedded in the program’s culture as a former player and long-time assistant coach under Nixon. [8] The transition has been seamless, a testament to the robust foundation of the program.
Under Coach Ollson, the Raiders have remained at the apex of high school football in Manitoba. The team continues to compete in the province’s highest AAAA division, consistently fielding championship-caliber rosters. The 2024 season was a prime example of their sustained excellence; the Raiders stormed through the regular season with a perfect 7-0 record, scoring an incredible 346 points while their defense did not allow a single point. [15] Their journey ended in the AAAA final, but their performance earned the program an impressive 6th-place ranking in all of Canada, proving that the future of Oak Park football is incredibly bright. [8][15]
The enduring strength of the program is also supported by a dedicated alumni base, formalized through the Oak Park Raiders Football Alumni Association, which helps to fund and support the team’s future. [16] The story of the Oak Park Raiders is not just about wins and losses; it’s about the creation of a lasting culture. From its formal inception in 1991, through the dynasty-building years of Stu Nixon, and into its current era of sustained success, the program has been a model of excellence. It stands as a powerful example of how dedicated coaching, community support, and a commitment to developing both athletes and individuals can forge a legacy that is unmatched in Canadian high school sports.