My biggest L was probably Season 54 with the Vancouver Whalers. After coming off a tough year where the team struggled to adapt to FHM and only won 17 of 50 games, we had high hopes going into the season after a pretty good draft. A 3-1 start seemed to solidify this, but then the wheels completely fell off. The Whalers lost something like 18 of the next 20 games after that and nothing we did worked. Our best strategy was just hoping our goalie Name Redacted could make 35-40 saves and we could win a game. We went 11-37-2 and blew up the team, selling off our captain Sven Yxskaft and our 1C Stracimir Petrovic for picks. Thankfully, this tank job ended up paying off in the end, as we made six draft picks in the ensuing draft that all ended up being key contributors to our championship team in S56. As they say, no pain, no gain.