yeah, the 1989 16-2 Eskies were another team that owned the league and pooped out in the playoffs ... opening the door for the 9-9 Riders to win their second stripe. I think 16-2 makes that team the best regular season team ever.
The 87 Bombers -- according to Cal Murphy, the best team he ever coached -- were cruising fat and happy at 12-6 until they inconceivably shat the bed in the eastern final.
Of course, everyone remembers the agony of the 2001 Bombers.
More recently the Bombers have turned 7-1 (2011) and 5-1 (2014) starts into playoff heartbreak (no-playoff heartbreak in 2014's case) I remember Swaggerville, and how Drew Willy was playing like Drew Brees for us and how quickly that bubble popped when he started getting hurt.
Regular season record means nothing when the temp gets low and the stakes get high. I agree with folks here that the 2021 Bombers just seem way more fundamentally sound than those gimmicky / lucky 2011 and 2014 teams and that O'Shea is right to keep them focused on not being too proud to compete .... but they still gotta deliver the goods in the wintertime to get the trophy.