Kind of connected to my other thread (which was resurrected today) about franchise failures. But this time: Which previously successful / awesome / dynastic / iconic franchise had the saddest fall from grace?
My selections to choose from:
Detroit Red Wings
Grace period: 1942 to 1957 (still competitive, on-and-off, from 1957 to 1970)
Fall from Grace: 1970 to 1986
The Wings' sixteen-year fall will be forever known as the 'Dead Wings' era. During this heinous period, they had exactly one winning season (and none whatsoever from '73 to '86... ouch!). From 1971 to 1983, they made the playoffs... once. The team actually reached its low-point in 1985-86 (at .250) just before recovery began when the Ilitches hired Jacques Demers, who made Steve Yzerman captain.
Toronto Maple Leafs
Grace period: 1940 to 1951, and again roughly 1959 to 1967 (still somewhat competitive from 1967 to 1979)
Fall from Grace: 1979 to 1992
The Leafs' thirteen-year fall will be forever known as the 'Ballard' era, when the team itself was often called the 'Maple Laughs'. The sexist, homophobic, profane majority owner (Ballard) drove the franchise into the ground safe in the knowledge that no matter how awful the team was, the loyal fans would still fill the building and guarantee revenue (which indeed they did). This horror-show thirteen year period featured no seasons with the Leafs over .500, with the 1984-85 (.300) season perhaps being the nadir.
New York Islanders
Grace period: 1975 to 1984 (still competitive from 1984 to 1988)
Fall from Grace: 1988 to 2001
The post-Potvin Islanders fell to .381 in 1988-89 (Billy Smith's last season) and didn't really recover until 2001-02. This wretched period included no fewer than seven seasons with a win-percentage in the .300's. The latter part of this era was topped-off by GM Mike Milbury's remarkable capacity for trading away young talents and signing/drafting ordinary players. (However... out of nowhere, the 1992-93 Isles had a decent season and took down the defending Cup champs in the second round, before losing in the Conference series. So, there was that.)
Edmonton Oilers
Grace period: 1981 to 1992 (still competitive from 1996 to 2006)
Fall from grace: 2006 to 2019 (ongoing)
The post-Dynasty Oilers fell badly circa 1992 to 1996, but this was mainly down to lack of revenue, not team management. They recovered, and made a Cup-run in spring 2006. Since then, they've been the worst team in the NHL, cumulatively, over an almost 13-year period, despite four 1st-overall draft picks in six years. The usual revolving door of coaches and GMs has highlighted this dark era. Superstar Connor McDavid is about to miss the playoffs for the third time in four years, while the franchise as a whole will do so for the twelfth time in thirteen seasons (2016-17 being the lone, brief, bright spot).
In short, then, which franchise (has) had the saddest fall from grace?
