Photo: Winnipeg Blue Bombers

It feels like the Winnipeg Blue Bombers are at a crossroads after failing to reach the Grey Cup for the first time since 2018, suffering a first-round playoff exit against the Montreal Alouettes in last month’s East Semi-Final.

The club was the class of the CFL for at least a half-decade but having sustained success in professional football means consistently finding fresh, top-tier talent while also balancing how many high-paid veterans are on the roster. Mike O’Shea is back as head coach and the club has doubled down on Zach Collaros at quarterback. Outside of that, there are many questions left to be answered for 2026.

Below are 10 pending free agents the team should re-sign from their list of 35 players currently set to hit the open market. Please note that “N” denotes nationals (ie. Canadians), “A” denotes Americans, and “G” denotes Globals.

Honourable mentions include receiver Keric Wheatfall (A), offensive lineman Tui Eli (N), defensive back Michael Griffin II (A), and special teams ace Tanner Cadwallader (N).

10) DL Willie Jefferson (A)

The soon-to-be 35-year-old seems to enjoy playing in Jordan Younger’s system despite mostly being asked to contain the passer as part of a three-man front. Jefferson’s sack totals have diminished in recently years due to scheme and age, though he remains the league’s best player when it comes to knocking down passes.

The six-time All-CFL selection plays a critical leadership role in Winnipeg, lives in the city year-round, and is one of the faces of the franchise. Though he’s no longer worth $200,000 per season, the Blue Bombers would be wise to bring Jefferson back for one last hurrah while simultaneously developing some young edge rushers around him.

9) K Sergio Castillo (A)

The native of La Joya, Texas connected on 85.7 percent of his field goals in 2025 despite averaging 37.5 yards per attempt, which was the longest in the CFL. Castillo went a perfect 31-of-31 on field goals from inside 40 yards, while also proving he can hit the deep ones by going six-of-eleven from 50-plus yards.

Good kickers are hard to find — Canadian, American, or otherwise. The one-time All-CFL selection and one-time Grey Cup champion is showing no signs of slowing down and brings affable presence to the locker room. If the Blue Bombers are smart, they’ll bring ‘Serge’ back for another season in 2026.

8) OL Stanley Bryant (A)

Though he’s no longer in a class unto himself, Bryant was still the sixth-best offensive tackle in the CFL in 2025, as per Pro Football Focus (PFF), and was voted a CFLPA all-star by opposing defensive linemen. If pass-rushers around the league think Bryant is still a top left tackle, Winnipeg should bring him back for an eleventh season in blue and gold.

Bryant has already taken a pay-cut since his days as the league’s perennial Most Outstanding Offensive Lineman and might be willing to take a little bit less again in 2026. Left tackles are hard to find and it wouldn’t make sense for Winnipeg to move on from Bryant until his game collapses or they find a worthy replacement.

Photo: Neil Noonan/3DownNation. All rights reserved.

7) DL Cameron Lawson (N)

The 27-year-old native of Caledon, Ont. needs to improve against the run but has quietly become one of the CFL’s best interior pass-rushers, particularly among Canadians. Lawson has cut weight since his collegiate days at Queen’s University and has fully recovered from the torn ACL that caused him to miss all of 2024, making him poised to enter his prime.

The six-foot-three, 290-pound defender has been a rotational player since joining the Blue Bombers in 2022 but some sources around the league have quietly questioned why he’s not a starter. Though he’ll likely need a raise to return to Bomberland, Lawson should get the chance to be a first-stringer in 2026.

6) OL Patrick Neufeld (N)

Winnipeg’s offensive line has regressed in recent years but Neufeld was arguably the unit’s top performer in 2025. The soon-to-be 37-year-old was PFF’s fifth-best guard in the CFL (min. 100 snaps) and he earned the third-best run-blocking grade at 71.3, consistently helping open holes for Brady Oliveira.

Turning over an offensive line takes a lot of time, money, and draft picks. It’s possible that Gabe Wallace, Tui Eli, or Ethan Vibert could take big steps in 2026 or that the team will sign a top free-agent should one come available. If the Blue Bombers want to avoid taking any risks up front, however, bringing Neufeld back would make a lot of sense.

5) DB Deatrick Nichols (A)

The two-time All-CFL selection will turn 32 during training camp next season but he remains one of the league’s best boundary halfbacks, which is arguably the toughest position to play in the secondary. The native of Miami, Fla. is ultra-smooth in coverage and doesn’t shy away from contact when a ball-carrier heads in his direction.

Nichols has only recorded seven interceptions over five seasons with the Blue Bombers, though that’s largely due to how infrequently opposing quarterbacks throw his way. Given the team’s uncertainty at cornerback, Winnipeg would be wise to invest heavily at halfback again in 2026. Speaking of which…

4) DB Evan Holm (A)

The 27-year-old was named All-CFL for the first time in his career after recording 55 defensive tackles, six special teams tackles, four interceptions, and two forced fumbles in 2025. After initially looking out of place during his rookie training camp in 2022, you’d be hard-pressed to find a player in the league who has improved more than Holm.

The native of Edina, Minn. is already among the league’s highest-paid defensive backs, though he’ll likely command a raise this offseason after being named Winnipeg’s nominee for Most Outstanding Defensive Player. Holm’s young family lives just across the border in Minnesota, which makes Winnipeg a nice geographical fit.

Courtesy: Winnipeg Blue Bombers.

3) DB Redha Kramdi (N)

The native of Montreal, Que. is a proven ratio-breaker at strong-side linebacker, though he also started games at safety in 2025. Kramdi has been a film junky since his collegiate days at the Université de Montréal and is considered by many to be the glue in Winnipeg’s secondary — essentially serving as an extra coach on the field.

The five-foot-ten, 189-pound defender made 47 defensive tackles, two special teams tackles, one interception, and one forced fumble this season and remains just 28. Assuming he wants to return, the Blue Bombers would be smart to sign Kramdi to a long-term contract extension.

2) REC Nic Demski (N)

The five-foot-eleven, 212-pound target was Winnipeg’s best receiver in 2025, recording 67 catches for 1,001 yards and seven touchdowns. Demski has caught 29 touchdown passes since 2022, which puts him among the top scorers in the CFL over that time frame.

Demski will turn 32 later this month but can still take the top off opposing defences and is coming off his third-straight 1,000-yard season. The receiving corps needs a significant upgrade in Bomberland but Demski is a piece the team should hang onto until he can no longer produce at a high level.

1) RB Brady Oliveira (N)

Was there ever a doubt which player would be at the top of this list? Oliveira is one of only five Canadians ever to win Most Outstanding Player, a hometown hero, two-time All-CFL selection, two-time rushing leader, and Winnipeg’s best overall player.

The five-foot-ten, 228-pound ball-carrier has recorded four-straight 1,000-yard seasons and led the league with 5.8 yards-per-carry in 2025 (min. 75 attempts). He has also continued to improve as a receiver out of the backfield, catching a career-high 61 passes for 546 yards in 2025, while proving solid in pass protection.

The 28-year-old is already easily the league’s highest-paid running back but don’t be surprised if he earns a substantial raise regardless of whether or not he leaves Winnipeg, possibly even reaching the $300,000 range. It seems likely that Oliveira will be back with the Blue Bombers, though he’s made it clear he wants to play for a championship team and be fairly compensated while doing so.

The Winnipeg Blue Bombers finished fourth in the West Division standings in 2025 with a 10-8 record, qualifying for the playoffs as the crossover team before losing the East Semi-Final to the Montreal Alouettes. Zach Collaros threw for 3,048 yards, 17 touchdowns, and 16 interceptions over 13 regular-season games, going 6-7 as a starter.

The Blue Bombers ranked fifth in net offence, third in net defence, and eighth with a turnover differential of minus-eleven. The club’s leading rusher was Brady Oliveira with 1,163 yards, leading receiver was Nic Demski with 1,001 yards, and leading tackler was Tony Jones with 104 tackles. Winnipeg ranked first in attendance with average crowds of 32,343, which was a 3.7 percent increase from the previous year.