Cap Era Futility
Buffalo - 12 consecutive seasons outside of the playoffs and counting (11-12 - Present)
Edmonton - 10 consecutive seasons outside of the playoffs (06/07 - 15/16)
Carolina - 9 consecutive seasons outside of the playoffs (09/10 - 17/18)
Detroit - 7 consecutive seasons outside of the playoffs and counting (17/18 - Present)
Florida - 2 playoff appearances over 15 seasons (05/06 - 19/20)
Atlanta/Winnipeg - 2 playoff appearances over 12 seasons (05/06 - 16/17)
Columbus - 2 playoff appearances over 11 seasons (05/06 - 15/16)
Vancouver - 2 playoff appearances over 10 seasons (13/14 - 22/23)
Arizona - 1 playoff appearance over 11 seasons and counting (13 - Present)
Toronto - 1 playoff appearance over 11 seasons (05/06 - 15/16)
New Jersey - 1 playoff appearance over 10 seasons (13 - 21/22)
In a few weeks, Ottawa, Chicago, Anaheim and San Jose will all be a half decade or more into their down cycles as well.
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I don’t think you can pin all of that on bad management. 16 teams are going to miss the playoffs yearly. It’s a big number. Further expansion will exacerbate the issue.
That's unhealthy for individual franchises and the league itself. Toronto was largely irrelevant for a decade! It should happen and I think ultimately will.