Looking at the Habs this year is... well, pain.
And I'm starting to wonder, will they hit the 'Worst record for a team that was a Stanley cup finalist the year prior' record.
So what is that record in the NHL since it's start?
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In the NHL's "modern era", The 2006-7 Hurricanes (40-35-7 OTLs, or 40-42) had the worst record by a defending champion if you count the OTLs as losses (which the NHL doesn't exactly). If you count OTLs as ties (or just count "points"), then the 1995-96 NJ Devils had a slightly worse winning percentage if you count ties as half-wins (but still over .500), and the 1990-91 Edmonton Oilers won only half their games exactly (37-37-6) - but made the playoffs and advanced to the conference finals, so I'm not sure that is quite the same.
To find a team that was in the class of the other three leagues (the other 3 major leagues have a team around .333), you have to go all the way back before the original six era to the 1938-39 Chicago Blackhawks, who at 12-28-8 had a .300 winning percentage of non-tied games, or a .333 winning percentage if you count ties as half-wins. However, they're sort of a special case: the 1937-1938 Hawks won the championship with a record of only 14-25-9 - a .385 winning percentage counting ties as half wins!