It feels like the Winnipeg Blue Bombers are at a crossroads after failing to make the Gray Cup for the first time since 2018, exiting in the first round of the playoffs against the Montreal Alouettes in the East semi-finals last month.
The club has been the class of the CFL for at least fifty years, but sustained success in professional football means constantly finding fresh, high-quality talent while also balancing the number of highly paid veterans on the roster. Mike O'Shea returns as head coach and in the club there is doubled Zach Collaros' lead at quarterback. Beyond this, there are still many questions to be answered by 2026.
Below are 10 pending free agents that the team should re-sign. their list of 35 players who are currently set to hit the open market. Note that “N” denotes citizens (i.e. Canadians), “A” denotes Americans, and “G” denotes global citizens.
Honorable mentions include wide receiver Kerik Whitfall (A), offensive lineman Tui Ely (N), cornerback Michael Griffin II (A) and special teams ace Tanner Cadwallader (N).
10) DL Willie Jefferson (A)
The soon-to-be 35-year-old appears to enjoy playing in Jordan Younger's system, despite being asked to contain the passer more often than not as part of a three-man group. Jefferson's sack totals have decreased in recent years due to scheme and age, although he remains the league's best player when it comes to breaking up passes.
The six-time All-CFL player plays a critical leadership role in Winnipeg, lives in the city year-round and is one of the faces of the franchise. While he's no longer worth $200,000 per season, the Blue Bombers would be smart to bring Jefferson back for one last hurray while developing several young forwards around him.
9) C. Sergio Castillo (c)
The La Jolla, Texas native converted 85.7 percent of his field goals in 2025 despite averaging 37.5 yards per attempt, which was the longest in the CFL. Castillo was a perfect 31-for-31 on field goals from 40 yards out, and also proved he could hit deep, going six-for-11 from over 50 yards.
Good kickers are hard to find—Canadians, Americans, or anyone else. The former All-CFL player and one-time Gray Cup champion shows no signs of slowing down and is a welcoming presence in the locker room. If the Blue Bombers are wise, they will bring back Serge for another season in 2026.
8) OL Stanley Bryant (A)
Although Bryant is no longer his own man, he was still the sixth-best offensive player in the CFL in 2025, according to Professional Football (PFF)and was voted a CFLPA All-Star by opposing defensive linemen. If pass rushers around the league believe Bryant is still the best left tackle, Winnipeg should bring him back for an eleventh season in the blue and gold.
Bryant has already taken a pay cut since being the all-time leading offensive lineman, and he may want to take a little less again in 2026. Left tackles are hard to come by, and it doesn't make sense for Winnipeg to move on from Bryant until his game falls apart or they find a worthy replacement.
7) DL Cameron Lawson (D)
27-year-old native of Caledon, Ontario. he needs to improve against the run, but he has quietly become one of the best pass rushers in the CFL, especially among the Canadians. Lawson has lost weight since his days at Queen's University and has fully recovered from the torn ACL that forced him to miss all of 2024, allowing him to enter the prime of his career.
The six-foot-three, 290-pound guard has been a rotation player since joining the Blue Bombers in 2022, but some league sources are quietly wondering why he isn't starting. Although he will likely need promotion to return to the Bomberlands, Lawson should be given a chance to become a first-team player in 2026.
6) O. L. Patrick Neufeld (N)
Winnipeg's offensive line has declined in recent years, but Neufeld may have been the team's best player in 2025. The future 37-year-old football player was PFF'Fifth-best defensive back in the CFL (min. 100 snaps) and third-best run blocking grade at 71.3, consistently helping open holes for Brady Oliveira.
Changing an offensive line takes a lot of time, money and draft picks. It's entirely possible that Gabe Wallace, Tui Eli or Ethan Vibert could make big moves in 2026, or that the team will sign a top free agent if one becomes available. However, if the Blue Bombers want to avoid any risks, bringing Neufeld back would make a lot of sense.
5) D.B. Dietrick Nichols (A)
The two-time All-CFL player will turn 32 during training camp next season, but remains one of the league's best edge linebackers, perhaps the toughest position to play in the minors. The Miami, Florida native is very fluid and doesn't shy away from contact when the ball carrier is coming his way.
Nichols recorded just seven interceptions in five seasons with the Blue Bombers, although that has a lot to do with how rarely opposing defenders throw the ball to him. Given the team's uncertainty at the cornerback position, Winnipeg would be wise to invest heavily in the midfielder again in 2026. By the way…
4) DB Evan Holm (A)
The 27-year-old was named All-CFL for the first time in his career after making 55 defensive tackles, six special teams tackles, four interceptions and two forced fumbles in 2025. After initially looking out of place during rookie training camp in 2022, you'd be hard-pressed to find a player in the league who has improved more than Holm.
The Edina, Minnesota native is already among the league's highest-paid defensemen.although he will likely receive a promotion this offseason after being nominated for Most Outstanding Defensive Player by Winnipeg. Holm's young family lives just over the border in Minnesota, making Winnipeg a convenient geographic location.
3) DB Redha Kramdi (N)
Native of Montreal, Que. is a proven balance disruptor at linebacker on a strong team, although he also started games at safety in 2025. Crumdy has been a film junkie since his college days at the University of Montreal, and is widely considered to be the glue of Winnipeg's secondary – essentially serving as an additional coach on the field.
The five-foot-ten, 189-pound defensive back has 47 defensive tackles, two special teams tackles, one interception and one forced fumble this season and is just 28 years old. Assuming he wants to return, the Blue Bombers would be wise to sign Crumdy to a long-term contract extension.
2) REC Nick Demski (N)
The five-foot-eleven, 212-pound target was Winnipeg's leading receiver in 2025, recording 67 catches for 1,001 yards and seven touchdowns. Since 2022, Demski has caught 29 touchdown passes, ranking him among the CFL's leading pass rushers during that span.
Demski will turn 32 later this month, but he can still take over opposing defenses and is coming off his third straight 1,000-yard season. The Bomberland's receiving corps needs a major upgrade, but Demski is a player the team should hang on to until he stops performing at a high level.
1) RB Brady Oliveira (N)
Was there ever any doubt which player would be at the top of this list? Oliveira is one of only five Canadians ever named Most Outstanding Player, a hometown hero, a two-time All-CFL player, a two-time rushing leader and Winnipeg's best overall player.
The five-foot-ten, 228-pound ball carrier had four consecutive 1,000-yard seasons and led the league with 5.8 yards per carry in 2025 (minimum 75 attempts). He also continued to improve as a receiver out of the backfield, catching a career-high 61 passes for 546 yards in 2025 while proving to be a solid pass protector.
The 28-year-old is already easily the league's highest-paid running back. but don't be surprised if he gets a significant raise whether he leaves Winnipeg or not, perhaps even reaching the $300,000 range. It seems likely that Oliveira will return to the Blue Bombers squad, although he has made that clear. he wants to play for a championship team and get fair compensation.
The Winnipeg Blue Bombers finished fourth in the West Division standings in 2025 with a 10–8 record, qualifying for the playoffs as a crossover team before losing in the East semi-finals to the Montreal Alouettes. Zach Collaros threw for 3,048 yards, 17 touchdowns and 16 interceptions in 13 regular-season games while going 6-7 as a starter.
The Blue Bombers ranked fifth in net offense, third in net defense and eighth with a minus-eleven turnover margin. The club's leading rusher was Brady Oliveira with 1,163 yards, the leading receiver was Nick Demski with 1,001 yards, and the leading tackler was Tony Jones with 104 tackles. Winnipeg ranked first in attendance with an average attendance of 32,343, up 3.7 per cent from the previous year.
