One man's take -
This is a stacked field, and some of the best players in club and league history will be left off of the top 2 due to the depth at this position. 9 Blue Bomber Hall of Famers, 6 CFL Hall of Famers, 2 members of the 75th Anniversary all-time team, and a third who was feted on the 80th anniversary team, plus a Ring Of Honour member. So if my dismissal of some seems flippant or harsh, consider who I am comparing them against and not just take it as disregard for their skill. With 18 on the list, some will pale in comparison to others.
The also-rans:
Elewonibi, Gauthier, Hardrick, Thompson - these 4 each have only one divisional all-star nom (or in Thompson's case a CFL nod too), and aside from Moe, none were regarded as the team's best lineman in any year, award-wise. Hardrick needs to put many more years before he can rank with the upper echelon.
The "best on the team but not league-best" club:
January, Perez - they both got 3 straight nods as the team's best lineman, and January added three divisional all-star noms, but they were not graded as the best in the CFL when they played with Winnipeg, despite being tops on the team. Perez went on to CFL all-star status after going to BC, and January was a warrior who played through some brutal injuries (and was a real gentleman when I met him at a Bomber dinner - a "player's player" for sure).
The all-time great before he got here but winding down:
Gorrell - Was league-best in his years with Ottawa and Hamilton, but by the time he came to Winnipeg he was not the same dominant player. That is not to say he was not good, or even very good, but just not as brilliant as with other teams (think Dominic Hasek with the Red Wings - still really good, but a shadow of his Buffalo self)
Best in the league in their time but too short a tenure to compete with the legends (NOTE - with weaker competition they may have made an all-timer list):
Bryant, Gainor, Goodspeed, Huffman - Gainor played only 4 seasons but was an all-star and Grey Cup participant every time, a pretty great success ratio. Huffman is a CFL Hall of Famer and had 4 consecutive all-star nods and one of only two offensive lineman to be named the team's outstanding player. Goodspeed was a legit star who blocked for Charles Roberts and had the league accolades to his credit, but his 5 year tenure needed to be tripled to approach the best on this list. Bryant deserves special mention because he is one of only 4 Blue Bomber tackles to ever win the award as Best Lineman in the CFL, and only one of 2 to win it twice (in fact, he is the only Bomber to ever win it in consecutive years), but with only 4 years on the Bombers, he will need to keep up that pace for another 6 years at minimum to enter the discussion as best ever. Check back in a decade to see where he ranks.
A tier below the legends (NOTE 2 - again, on another team they may well top the list, but they are in tough here):
Mudge, Norman, Savoie - Mudge was the glue on the line for a team that reached fantastic offensive heights with Roberts and Stegall, and was the team's best for a 3 year run that included a league best award in '01 and all-star recognition. He is just a shade ahead of the group before him due to his games and years played. Savoie has less award and all-star recognition than his counterparts, mainly because the awards were not around when he played. But no one on the list (save one) played more years or games, or had more Grey Cup success than he did. And he's in the CFL Hall of Fame. He is in contention for top 5 placement on this list, no small feat. Norman was the team's best for 7 years and had some league recognition as well spread out over that time, a giant of a man on the line. His longevity puts him higher on the list, his lack of team success or Best Lineman award probably puts him below the other 2 in this category.
That leaves me with 4 superstars to choose from, all CFL Hall of Famers. Let's flip things and start with the easy choice as top of this field:
The best ever
Walby - Regarded as the best offensive lineman in CFL history. His stature now (6'7", 325 lbs.) would put him among the larger linemen in the league, but nothing outrageous, but at the time he was a giant in the tranches. Gaudy accolades - his 11 divisional nods are the best in club history at any position, and his 9 CFL all-star nods are the most of any tackle, tied for most of any o-lineman, and 2nd only to linebacker Willie Pless' (who had 11) in CFL history. Although not officially retired, his number 63 will not be worn again by any player for the foreseeable future. And the sole member on this list who graces the club's new Ring of Honour. He should be a unanimous pick here as not only top 2 but the best o-lineman in club history, regardless of position.
So who joins him? For me, from 4 to 2 it is as follows:
Bill Frank - if this list counted a player's accomplishments throughout his whole career, and not just with the Bombers, Frank would be #2 on this list I'd wager, and he still makes a pretty good argument anyway. He was a 3 time CFL all-star and best lineman nominee in 1967 with the Argos before coming to Winnipeg. He continued his dominance here, racking up 4 more league all-star nods and 4 club noms as outstanding lineman (the first 3 when he had to compete with the defensive linemen too). He also achieved something that almost no one ever has, being selected the club's outstanding player as an offensive lineman (granted the team was 2-14 that year). Splitting the thinnest of hairs, I rank him below the other 2 because he was not part of the all-time 75th anniversary or 80th anniversary teams, never got to the big dance, played a few less years than the others, and never won a league award for best lineman, none of which should detract from his amazing career.
Buddy Tinsley - a legendary name in Bomber history (and part of grey Cup folklore for "almost dying" in the Mud Bowl - a "fact" he said was exaggerated), he dominated on both sides of the ball during the glory years. Named to the all-time 80th anniversary Bomber team, he played over a decade with the team and had an astounding 7 all-star nods. Had there been awards for best lineman at the time he surely would have won, and he also played in 5 Grey Cups, winning 2. Just outside the cut line for me.
Frank Rigney - before Walby (who is the only offensive lineman other than Rigney named to the all-time Blue Bomber team that was selected in the team's 75th season), he was in the discussion for best offensive lineman of all-time in the CFL. With Walby, Bryant and Mudge, one of only 4 Bomber tackles to win the award for best lineman in the CFL. 7 divisional all-star noms, and "only" 3 CFL all-star noms because the league did not have that recognition until 1962 (he won his 3 in the first 5 years that they awarded it). He was also part of the greatest era of Bomber football ever, with 4 championship rings. Bonus points for coming from Iowa right after his QB Ken Ploen, and being the lead blocker for Leo Lewis. He will be my other selection as greatest Bomber offensive tackle ever. I will honestly be disappointed if he gets overlooked due to recency bias - he like Herb Grey deserves to be on this team.