The Winnipeg Blue Bombers are one of the most successful teams in Canadian Football League history. With 12 Grey Cups and a record 28 Grey Cup appearances, Winnipeg has been a consistent competitor in Canada’s top football league. For such success to happen, the front office has to draft, develop, and sign players reliably. Winnipeg did that successfully with Brady Oliveira and Willie Jefferson, two key players on Winnipeg’s last Grey Cup Championship team in 2021. Today, let’s look at what makes them such strong players on the Blue Bombers.

Who Is Brady Oliveira?

Oliveira is a hometown hero. He is a 26-year-old running back from Winnipeg, Manitoba. He finished his career at the University of North Dakota as the all-time leading rusher and garnered interest from National Football League teams.

At 5’10” and 225 pounds, Oliveira received no offers from the Power Five conference teams and elected to stay closer to home by attending North Dakota. During his career, he earned All-Big-Sky Conference honours in 2016 and 2017 and was a finalist for the Jon Cornish Trophy given to the best Canadian player in college football.

After his senior year, he was named the Red Jarrett Male Athlete of the Year at North Dakota and had his sights on the NFL. However, after going undrafted, his hometown Bombers took him in the 2nd round with the 14th overall pick in the draft.

Who Is Willie Jefferson?

Unlike Oliveira, Jefferson was not a hometown hero. Born in Beaumont, Texas, he was recruited by Pac-12, Big Ten, SEC, and Big 12 schools.

At  6’7″, he ultimately signed with Baylor as a wide receiver in 2009 and then moved to tight end in 2010. However, he was dismissed from the team after he was found asleep in his car in possession of marijuana with future NFL star Josh Gordon. It was his second drug policy violation, resulting in his dismissal.

He transferred to Stephen F. Austin University and was named the Southland Conference Newcomer of the Year in 2011. He moved to defensive end and racked up 16 sacks. He signed with the Texans as an undrafted free agent and appeared in six games with Houston before being cut. After spending time with the Buffalo Bills in 2014, he signed with the Edmonton Eskimos.

After two years in Edmonton, he got one more shot in the NFL with Washington but was again cut during Training camp. He broke out with the Saskatchewan Roughriders in 2017, recording eight sacks and making the CFL All-Star Team before recording his first double-digit sack season in 2018. He then signed a one-year deal with Winnipeg and has been there since.

How Successful Have They Been in Winnipeg?

Both players wound up in Winnipeg simultaneously and have helped lead the Blue Bombers to success as a constant football lines favourite. Jefferson has been an All-Star thrice in Winnipeg, including a 2019 season that saw him win the CFL’s Most Outstanding Defensive Player award.

Both were key contributors to the 2019 team that reached the Grey Cup but ultimately lost. In 2021, Jefferson made another All-Star team and helped lead the Blue Bombers to their 12th Grey Cup championship. Oliveira was the team’s second-leading rusher behind starter Andrew Harris.

However, Oliveira took the next step last season, taking over as the starter and having a career year that saw him named an All-Star alongside Jefferson. He rushed for over 1,500 yards, scoring nine touchdowns and adding nearly 500 yards through the air.

Both Jefferson and Oliveira’s performances helped lead the Blue Bombers to their fourth Grey Cup in five seasons, but they ultimately lost to the Montreal Alouettes. Oliveira was named the team’s Most Outstanding Player, while Jefferson was the team’s Most Outstanding Defensive Player for the second consecutive season.

Will They Stay With the Blue Bombers?

There was some doubt that Winnipeg would retain both players after their big 2023 seasons. Both were free agents after 2023, but Oliveira and Jefferson said they hoped to remain with the team through 2025 in a joint press conference after the season.

“Being a local kid here, playing for my hometown team is a dream come true, and I really don’t see myself going anywhere. I love the organization. I think it’s a great fit for me personally and my career, the role that I’ve stepped into and taken by storm last season,” Oliveira said in the press conference.

Both players are great for the community, receiving Blue Bombers Community Service Awards in 2023. Fans love these two players, and as long as they continue to deliver on and off the field, there is nothing to suggest Winnipeg would move on from their franchise players.

Who Is the Next Great Player for Winnipeg?

While Oliveira is still young in his career, Jefferson is 33 years old, and the Blue Bombers must be proactive in finding young talent to continue reaching Grey Cups. The 2024 CFL Draft is scheduled for April 30, and Winnipeg has more picks than anybody else in the draft. Maybe their next great player is waiting for them in the upcoming draft.